A while back, someone posted to r/chicago with the title I got 2 tickets for the same thing from the same officer. It picked up more than 700+ upvotes, because that mix of confusion and frustration is something most of us can definitely relate to. The top comment helpfully clarified that you’re only supposed to get one citation per violation per 24-hour period, even though they got a second one.

And while it’s worth a chuckle, it’s kinda the story of parking in Chicago, isn’t it? The rules exist, and sometimes they don’t get applied consistently, so sometimes we’re left baffled and sometimes with a slightly lighter wallet.

So this week, we figured it would be helpful to write a guide about everything parking-related in Chicago. This article covers what you’re required to have, what the signs mean, what tickets cost, and how to fight the ones you shouldn’t have gotten.

To be clear, we’re not parking enforcement officers. We’re just one of the top-producing real estate teams in all of Illinois. The Ben Lalez Team has been helping families buy and sell homes across Chicago for over a decade, and every week we put out an article about something useful or interesting about the city.

You are welcome to subscribe to our newsletter if you want these in your inbox. In the meantime, let’s get going.

The City Sticker

Every Chicago resident who uses a vehicle in the city is required to have a city vehicle sticker, regardless of where the car is registered. This is the local wheel tax, and it is not optional. You have 30 days from moving to Chicago or purchasing a vehicle to buy and display one.

For most passenger vehicles, the sticker runs around $90 per year. Motorcycles and mopeds pay a separate wheel tax via a medallion fixed to the plate. You can purchase through the City Clerk’s office, online through the city’s EZ>BUY portal, or at most currency exchanges. You’ll need your ID, registration, and proof of Chicago residency.

The penalty for not having one is pretty steep: at least $200 per ticket. Given that inspectors are very active and the violation is easy to spot, this is one of the cheaper problems to avoid.

Residential Zone Permits & Guest Passes

Residential Permit Parking zones limit street parking to local residents and their guests during posted hours. In high-demand neighborhoods, those hours can cover overnight or the entire day. If your block is zoned, a car parked there without the right credentials gets ticketed.

There are two credentials that matter: 

• a zone-specific city sticker
• daily guest passes

Adding a zone to your city sticker costs around $25 to $30 per year and requires that your address falls within that zone. The zone number printed on your sticker must match the number on the street sign. A Zone 383 sticker does nothing on a Zone 606 block, even if those two streets are one block apart.

Guest passes are sold in sheets and are typically around $15 for 15 passes, though pricing varies by ward. Each pass is valid for 24 hours from the written start time. There’s a city-imposed cap of roughly 30 passes per household every 30 days. If you have frequent visitors, those go fast.

Remember… a residential zone permit does not override meters, rush-hour tow zones, street cleaning restrictions, or snow bans. It only handles the “resident permit required” requirement. If any of those other rules apply to a block, the zone permit doesn’t protect you from them. You’ve been warned.

Street Cleaning

Street sweeping runs from roughly April 1 through November 30. Parking on a posted cleaning route during the sweep window gets you a ticket of around $60, and on major streets, it sometimes gets you a tow as well.

Some blocks have permanent street-cleaning signs with fixed days and hours. Many residential blocks use temporary paper or plastic signs posted before each sweep. Courts have held that the city must give at least 24 hours of notice before a street-cleaning ticket is valid, which matters when signs go up late.

If you park somewhere unfamiliar, take a photo of the sign. If the sign was posted less than 24 hours before the window it covers, that’s grounds to contest. The city has a history of issuing tickets on late-posted signs, and local news has covered cases where those tickets were successfully challenged.

You can also set calendar alerts. The city publishes sweeping schedules, and several third-party apps track the routes. It takes five minutes to set this up, and this is the best way to avoid tickets.

Winter Parking Bans

Yes, we know you don’t want to hear about winter since we’ve just finally got some good weather, but bookmark this page anyway. 

Chicago runs two separate winter parking systems, and most residents only know about one of them.

The overnight parking ban covers approximately 107 miles of main streets from December 1 through April 1. During those months, parking on those designated streets is prohibited every night from 3am to 7am, regardless of whether it has snowed or is expected to snow. This applies every night of that four-month stretch.

The snow-route ban works differently. It covers roughly 500 additional miles of streets and kicks in whenever there are at least two inches of snow on the roadway, regardless of date or time. This one can trigger in late October or during a surprise spring snowstorm, so the seasonal overnight ban and the snow ban are not the same thing and do not cover the same streets.

Parking in a banned spot during winter hours can cost you: a $60 ticket, a tow running around $150, and storage fees of approximately $25 per day at a city impound lot. That adds up fast if you can’t get there until the next morning.

When you move to a new block, pull up the city’s snow-route map. The signs on a single pole can show both a snow-route designation and a seasonal overnight restriction.

Everyday Rules That Catch People Off Guard

A few basics that show up on tickets more than you might expect:

• Your car must be within 12 inches of the curb
• Do not park on sidewalks, parkways, or crosswalks
• Keep at least 15 feet from fire hydrants and 20 feet from crosswalks or stop signs
• Alleys are not parking spots (you can briefly stop to load or unload, but leaving a car in an alley is a ticket)
• Bus lanes and bike lanes are not parking lanes at any time.
• Downtown, some streets shift function during rush hours: a block that operates as a loading zone during the day becomes a full tow-away traffic lane during peak hours, and stopping there at the wrong time gets the car towed even if you’re sitting in it.

Meters vary by area. Rates run from roughly $2 to $6.50 per hour, with the Loop at the high end. Most are managed through traditional meters or the ParkChicago app. If you pay through the app and still receive a ticket, screenshot the payment confirmation immediately and contest with that receipt. This comes up often and is one of the more winnable ticket disputes.

Event Days In High-Demand Neighborhoods

Near Wrigley Field, street parking in Lakeview is heavily restricted during Cubs night games. In Zone 383, which covers much of the surrounding area, cars on specific blocks must display a 383 residential permit or guest pass during posted event hours. 

That restriction applies on top of whatever the normal residential zone rules are for the block. If you’re heading to a game without a resident permit, the neighborhood garages and pre-booked apps are your best option.

The same applies near Soldier Field. During Bears games and large stadium events, many streets in the South Loop that are otherwise legal to park on require residential permits or event-specific passes. 

The practical rule on event days: re-read every sign on the block, even if you’ve parked there before. Event restrictions are sometimes added temporarily and don’t always look like the permanent signs you’re used to seeing.

Tickets, Booting, and Contesting

Chicago’s ticket system is massive. The city has issued tens of millions of parking and compliance tickets since 2007, and outstanding ticket debt reached roughly a billion dollars at its peak. City sticker violations alone start at $200 per ticket with additional late penalties. Courts have found that Chicago has, in some cases, overcharged residents by stacking more than the state-allowed $250 in fines and penalties on individual violations.

You can search, pay, and contest parking tickets through the city’s online portal. 

If you plan on fighting a ticket, you have 7 days from the date of the ticket to start the process. After the city mails a Notice of Violation, you have 21 days to request a hearing. If an automatic guilty finding goes through, you have another 21 days to ask a judge to reverse it, after which the ability to contest is gone, and the full fine is final.

If unpaid tickets accumulate, the city can boot your car. Once booted, you have 24 hours to pay or enroll in a payment plan before the car is towed, which adds tow and storage fees on top of everything already owed. Old tickets don’t expire. They can be sent to collections and surface in the system years later.

Payment plans are available through the city’s portal and let you bundle multiple tickets. If the total owed is significant, do this before the city decides to boot your vehicle.

A Quick Checklist

• Get your city sticker within 30 days of moving or buying a car.
• If your block is in a residential permit zone, add the correct zone to your sticker and keep a sheet of guest passes on hand.
• Check your zone number against the sign, not just the neighborhood.
• From April through November, check for street-cleaning signs before leaving the car anywhere unfamiliar.
• Before December 1, look up which streets in your area are on the overnight ban and the snow-route map.
• On event days near Wrigley or Soldier Field, re-read every sign, even on blocks you’ve used before.
• If you pay a meter through ParkChicago and still get a ticket, screenshot the app receipt and contest it.
• Don’t let tickets sit. It can get very expensive.

Frequently Asked Questions

My car has out-of-state plates, but I live in Chicago. Do I still need a city sticker?

Yes. The requirement is based on residency, not registration. If you live in Chicago and use a vehicle here regularly, you need the sticker within 30 days of establishing residency, regardless of where the car is registered. Out-of-state plates don’t exempt you.

I’m visiting a friend for a week. Do I need anything to park on their street?

If their block is a residential permit zone, your car needs either a zone-stamped city sticker or a guest pass on the dash during posted hours. Your friend provides the guest pass from their household allotment. If the block isn’t a permit zone, standard parking rules apply, and no pass is needed. Check the signs on the specific block.

How long can I leave my car on the same street?

Chicago has a 72-hour rule: a vehicle left on the same city street for more than 72 consecutive hours can be cited as an abandoned vehicle and towed. This catches people who park before a long trip and come back to find the car gone. If you’re leaving for more than three days, put the car in a garage.

Is street parking free on Sundays?

It depends on the block. After the city’s 2008 parking meter privatization deal, some wards negotiated free Sunday metered parking, and others did not. In many neighborhoods, meters run seven days a week. Check the sign on the specific meter rather than assume Sunday is free.

What about holidays – are meters free?

The city generally relaxes meter enforcement on designated city holidays, but the list can change, and there are exceptions. Residential permit zones typically still apply even when meters aren’t being enforced, so a free-meter day doesn’t mean you can park in a permit zone without credentials. Check the signs regardless.

If I have a disability parking placard, do I still have to pay the meter?

It depends on the placard type. Illinois changed its rules so that only certain placards issued under stricter eligibility criteria are meter-exempt. A standard blue placard no longer guarantees free meter parking in Chicago. If you’re unsure whether your placard qualifies, check with the Illinois Secretary of State’s office before assuming the meter is covered.

Can someone else in my family use my disability placard when I’m not in the car?

No. Placards are issued to the individual and are valid only while that person is being transported. Using a placard when the permit holder isn’t present is a violation, and it’s a common reason enforcement has tightened on this in recent years.

Is it worth renting a monthly parking spot in neighborhoods like Wicker Park, Lincoln Park, or Lakeview?

The math often works out in favor of renting one. Monthly spots in those neighborhoods typically run $150 to $250. A single city sticker violation starts at $200 before late fees. A tow plus storage runs $175 or more. One bad week can cost more than two months of a dedicated spot. For residents in high-demand permit zones who drive regularly, a monthly garage spot often costs less than the cumulative risk of tickets over a year.

Can I really get two tickets in one day for the same violation?

Technically, the rule is one citation per specific infraction per 24-hour period. In practice, some drivers do receive duplicate tickets, which is the situation in the intro of this article, and not a rare one. If you get two tickets for the same violation issued the same day by the same officer, fight the second one. Bring both tickets to the hearing and clearly note the duplicate.

Final Thoughts

If you’re diligent and know the rules, you’ll be unlikely to get a surprise ticket. The people who get caught repeatedly are usually missing one piece: the zone permit they never added, the snow-route designation they didn’t look up, or the event restriction they assumed didn’t apply because it was a normal Tuesday the last time they parked there.

Parking is just one of those life activities we have to deal with when living in a big city like Chicago. Hopefully, this guide saves you frustration, time, and some money!

And if you’re house hunting and parking near the lakefront or Wrigley is part of what you’re thinking through, reach out to us! It comes up in a lot of neighborhood conversations, and it’s worth factoring in if you’re thinking about buying soon!

The post The Ultimate Guide To Parking In Chicago appeared first on Ben Lalez.

Most people who don’t live here assume Chicago is a city you experience from the inside: museums, restaurants, architecture, sports. What they might be surprised about is that Chicago has 28 miles of Lake Michigan shoreline and about 27 publicly maintained beaches, all of them free.

At the time of this article, 4 beaches are closed indefinitely due to erosion, so it’s important to check the Chicago Park District’s website before heading out.

We find that most Chicagoans stick to one beach and don’t bother exploring all their options. North Avenue gets crowded, Montrose gets discovered, and the entire South Side of the lakefront goes largely unvisited by people who live in the same city. This guide covers what’s at each major beach, not just the well-known ones, so you can pick the right one for your day.

We’re the Ben Lalez Team, and we’ve been helping families buy and sell homes across Chicago for over a decade. Every week, we put out an article about something useful or interesting about the city. Subscribe to our newsletter if you want these in your inbox.

Okay, let’s get into it!

How The Chicago Beach System Works

Beach season runs from Memorial Day weekend through Labor Day. Swimming is allowed only when lifeguards are on duty, which is daily from 11am to 7pm. Outside those hours, red flags go up, and swimming is not permitted.

Each beach posts a flag indicating current conditions. 

• Green means swimming is allowed and water quality is acceptable.
• Yellow means use caution.
• Red means no swimming, whether due to weather, strong currents, or water quality. 

The Chicago Park District publishes daily swim status online by beach, and it’s important to always check before you leave home. Weather conditions affect access, and after heavy rain, runoff pushes bacteria levels higher near the shore.

The rules are the same across all beaches:

• no alcohol
• no glass containers
• no smoking
• no dogs on the sand except at designated dog-friendly areas
• grilling is allowed only in designated spots, and hot coals go in the metal barrels provided.

Park District staff enforce these at the busier locations, so make sure you know the rules.

Downtown Beaches

The central beaches draw the largest crowds and have the most amenities. They’re what most people picture when they think about Chicago having a lakefront.

North Avenue Beach is the loudest, most active beach in the city. The beach house is shaped like a ship and features restrooms, lockers, and Castaways Bar and Grill, which offers both counter service and sit-down dining with lake views. Volleyball courts stay busy on weekends, and on-site rentals cover jet skis, kayaks, paddleboards, and bikes. If you want energy, activity, and a social scene, this is the beach for you.

Oak Street Beach is in the Gold Coast, just south of North Avenue, and has the most photographed skyline backdrop of any beach in the city. The shot from Oak Street looking back at the Chicago skyline is the one that ends up in travel guides and real estate listings. Concessions are on-site, and the underpass near the beach has a mural by artist Jeff Zimmermann that is popular for photos. The stretch of sand is shorter than North Avenue, but the views are better.

Ohio Street Beach is just east of Navy Pier in a protected cove, which makes the water calmer and the overall experience quieter than the other two central options. Open-water swimmers and triathletes use it regularly for training. The sheltered cove is easy to navigate and connects directly to the Lakefront Trail for running and cycling. If you want a beach close to downtown without the North Avenue crowd, Ohio Street is the one.

North Side Beaches

Moving north from North Avenue, the beaches take on more of a neighborhood character. The crowds shift from citywide social scene to local regulars.

Montrose Beach is the largest beach in the city by area. There are volleyball courts and water sport rentals, but what sets Montrose apart is everything else. The Montrose Dunes and Bird Sanctuary is located directly adjacent, a protected natural area that draws bird watchers and people who want to walk. There’s also a designated dog-friendly section where dogs can run off leash in a fenced area near the water.

Foster Beach at Foster Avenue is the North Side beach for dog owners who don’t want to make the trip all the way to Montrose. It has a designated dog-friendly area, concessions, restrooms, and lifeguards in season. The crowd is mostly local, so you can usually find a spot, even on a busy weekend.

Osterman Beach, known to locals as Hollywood Beach, is further north near Edgewater. It’s another neighborhood beach with sand, lifeguards in season, and lakefront trail access. If you live on the Far North Side, this is likely your closest option. The smaller street-end beaches like Lane Beach in Edgewater follow the same logic: direct lake access, almost entirely local crowd, no concessions, no rentals, just sand and water.

South Side Beaches

The South Side beaches are less crowded than anything on the North Side. Several have better parking, and some are located next to institutions that make for a full day rather than just a beach trip.

31st Street Beach is the most accessible South Side option, at 31st Street Harbor and with skyline views looking north toward downtown. Amenities include concessions, restrooms, parking, a playground, and lakefront trail access toward the Museum Campus.

57th Street Beach is inside Jackson Park, directly next to the Museum of Science and Industry. It’s a good option for families who want to split a day between the museum and the lake. The beach is straightforward, with sand, water, and park facilities nearby, and the Jackson Park has lots of green space to enjoy.

63rd Street Beach has one of the more historically significant beach houses on the lakefront, a Prairie-style structure from 1919 that has been restored. Just south of it is South Shore Beach, which sits on the grounds of the South Shore Cultural Center, a building that was originally a private country club before the Chicago Park District acquired it in 1974. The Cultural Center has a golf course, gardens, a ballroom, and event spaces built into what is now a public park.

Rainbow Beach is further south and combines swimming with one of the city’s oldest public gardens and a natural dune area called the Rainbow Beach Dunes. The amenities are quite good: concessions, playgrounds, restrooms, Wi-Fi, handball courts, and a fitness center. It functions as a full community park with a beach attached, and it draws a consistent local crowd.

Calumet Beach is the southernmost beach in the city, near the southeastern border. It’s uncrowded by any central beach standard, almost entirely local, and not on most people’s radar. For residents of the Far South Side, it’s the neighborhood beach. For anyone else, it’s a reason to explore a stretch of the lakefront that the rest of the city ignores.

Choosing the Right Beach

A few scenarios worth working through before you load the car:

For the most active social scene, North Avenue and Oak Street are the obvious choices. They’re the busiest for a reason, and both offer full on-site amenities.

For open-water swimming or triathlon training, Ohio Street Beach has the protected cove and the cleanest transition to the Lakefront Trail.

For dog owners, Montrose and Foster both have designated off-leash areas. Montrose has more space. Every other beach on the lakefront prohibits dogs on the sand.

For combining a beach with a cultural site, 57th Street is next to the Museum of Science and Industry, and South Shore sits on the grounds of the South Shore Cultural Center.

For a neighborhood beach without downtown energy, Foster, Osterman, 31st Street, and Rainbow all deliver.

For parking, the South Side beaches are generally easier. The North Side central beaches are designed around transit and bike access, and parking reflects that.

One More Thing On Water Quality

Blue-green algae blooms occur in Lake Michigan during warm months and are harmful to both people and dogs. The Park District posts advisories, and the daily swim status includes current conditions by beach. Check before you go, especially after a stretch of hot days when bloom conditions are most likely near the shore.

Final Thoughts

Chicago’s lakefront is one of the things this city has that most American cities don’t: 27 free public beaches, open all summer, reachable by transit from almost anywhere in the city. Most residents pick one and stick with it. So if you’ve spent every summer at North Avenue and never made it to South Shore or Rainbow, go check them out.

And if you’re thinking about buying somewhere close to the shoreline and proximity to the lakefront is important to you, give us a shout. It comes up in almost every conversation about the North Side neighborhoods, and we have a ton of suggestions for you when you’re ready to look.

Make sure to stock up on that sunscreen, and see you out there on the sands!

The post A Guide To Chicago’s Beaches appeared first on Ben Lalez.

It’s finally summer, and that means we have a small window of time to enjoy the lakefront before winter crashes the party at the end of the year. 

Chicago has 26 miles of shoreline and dozens of beaches along Lake Michigan, so there are lots of options whether you want to play volleyball, go paddling, or just sit in the sand and people watch while you work on your tan.

We’re The Ben Lalez Team, and we’ve travelled through pretty much every neighborhood in the city. Although we’re experts in real estate, we also know all the best spots to enjoy everything Chicago has to offer.

In this guide, we share the best urban beaches in the city, and we hope you find a favorite to enjoy this summer!

North Avenue Beach

1600 N. Lake Shore Drive in Lincoln Park

This is Chicago’s most famous beach. Here you’ll find the Art Deco beach house that was built in 1934. If you’re into volleyball, you’ll see everything from serious tournaments with teams that have matching jerseys to random pickup games that go all afternoon.

Features: Volleyball courts everywhere, bike rentals, kayak rentals, jet ski rentals, the Castaways Beach Bar, and the Shore Club up on the beach house roof. The Lakefront Trail runs right behind everything.

Most popular with: Active people, volleyball fans, and anyone who wants the Chicago beach experience.

Scene: There’s music blasting from the beach bars and the downtown skyline right in front of you. It gets busy on summer weekends, so if you want a decent spot, you’ll need to arrive early.

Quick facts: If you’re into volleyball, check the tournament schedule to see when events are happening.

Oak Street Beach

1000 N. Lake Shore Drive in Streeterville

This is smaller and more upscale than North Avenue, sitting right next to the Magnificent Mile. The sand area isn’t huge, but the skyline views are incredible. You’ll see lots of people taking photos of the waterfront.

Features: Beachfront cafe, chair and umbrella rentals, bicycle rentals, and volleyball courts. Don’t forget to take a photo of the famous rainbow mural.

Most popular with:  Tourists, couples, and families. This is a good beach if you’re mixing beach time with shopping or sightseeing in the area.

Scene: More relaxed than the bigger beaches. Evening visits are really nice when the downtown starts lighting up.

Quick facts: During summer, the Paris Beach Bar and Whispers Beach Club set up seaside cabanas right on the sand.

Montrose Beach

4400 N. Lake Shore Drive in Uptown

Montrose is Chicago’s biggest beach, so it feels more like a beach park than just a regular beach. There are areas that are protected bird habitats so you’ll get the experience of a regular beach as well as some nature.

Features: The Dock restaurant with outdoor seating, bike rentals, volleyball courts, launch area for kayaks and canoes, and Chicago’s only official off-leash dog beach on the north end. They also have a beach wheelchair available for accessibility.

Most popular with:  Dog owners, families looking for more space, birdwatchers, and kiteboarders. It’s the only beach in the city where kiteboarding is allowed.

Scene: Relaxed and community-focused with lots of locals who come here regularly. You’ll see families barbecuing and dogs running around in the water.

Quick facts: Montrose Point Bird Sanctuary is right next to the beach and attracts tons of migratory birds in the spring and fall. The dog beach section is completely fenced and off-leash, so your dog can actually run free and splash around.

Foster Avenue Beach

5200 N. Lake Shore Drive in Edgewater

This is a wide, clean beach with a more natural feel. The pink concrete beach house from 1934 is pretty hard to miss when you’re driving by. It has that natural, undeveloped feel while still offering all the amenities you need.

Features: Historic beach pavilion with food concessions, bike and scooter rentals, changing areas, showers, beach wheelchair for accessibility, plus there’s a playground and ball fields just behind the dunes.

Most popular with:  Nature lovers, families who want playground access for their kids, dog owners, and fitness enthusiasts.

Scene: Casual neighborhood beach with more character than some of the others. You might catch drum circles or someone playing acoustic guitar at the beach house patio on summer evenings. Tall red pines and wildflowers give it a different look from the more urban beaches.

Quick facts: Locals call the pink beach house the “Pink Palace” and it’s actually a historic landmark. The dune trails behind the beach have some rare native plants if you’re into that kind of thing.

Kathy Osterman Beach

5755 N. Lake Shore Drive in Edgewater (people also call it Hollywood Beach)

This is a wide sandy beach with calm, shallow water that’s perfect for paddleboarding and just wading around. The LEED-certified beach house from 2010 is modern and won some environmental awards. This is also Chicago’s unofficial LGBTQ+ beach.

Features: Two paddle and kayak launch areas, concessions, restrooms, a modern beach house with showers, and a splash fountain playground for the kids.

Most popular with:  The LGBTQ+ community, dog owners, paddle sports lovers, and anyone looking for a welcoming, peaceful environment where they can relax.

Scene: Open and inclusive, very laid-back. It’s normally less crowded than the more central beaches. The water is clear and shallow, and there’s usually some music from friendly groups gathering on the sand.

Quick facts: The silver LEED-certified beach pavilion has a rooftop deck and actually won design awards when it was built. This is also the northern terminus of the 18-mile Lakefront Trail, so it’s a popular starting or ending point for long bike rides.

Loyola Beach

1230 W. Greenleaf Avenue in Rogers Park

This is one of the quietest beaches on the lakefront, located next to Loyola University. Next to the beach is Loyola Park with 21.5 acres of recreation space, including fields and courts.

Features: Sand volleyball courts, tennis courts, playground, picnic areas, restrooms, and showers. The park has a historic fieldhouse from the 1920s, baseball fields, and basketball courts.

Most popular with:  Families, college students, nature lovers, and anyone looking for a peaceful spot away from the tourist crowds. Birdwatchers and joggers really like the 2/3-mile lakeside loop path.

Scene: Calm and park-like with a more relaxed atmosphere. You’ll hear the waves and birds, and casual conversation instead of loud music and crowds. It’s perfect for reading a book or just sitting and listening to the water.

Quick facts: The 1920s fieldhouse has a gym and boxing center that’s still active. This beach also runs an ABA junior lifeguard training program, so you might see teenage lifeguards practicing their skills during the summer.

Leone Beach

1222 W. Touhy Avenue in Rogers Park

This is a smaller, quieter beach just north of Loyola with about 250 feet of shoreline. The brick pavilion used to be a pumping station, which gives it some character. It’s squeezed between high-rise apartments and feels like a neighborhood secret that not many tourists discover.

Features: Playground, kayak and canoe launch ramp, restrooms, spray fountain for kids, and the old brick fieldhouse that can be rented for events.

Most popular with:  Kayakers and canoeists, families, and people interested in Chicago history. The calm waters make it especially good for beginners trying out paddle sports.

Scene: Quiet and very local with a neighborhood feel. Not many tourists go this far north, so it feels like a community gathering spot. Mornings are peaceful with walkers and joggers, while summer afternoons bring families for picnics.

Quick facts: This is home to Chicago’s Junior Lifeguard program, which was named after Sam Leone, a legendary lifeguard supervisor. The pavilion building dates back to 1900, making it one of the oldest lakeside structures in the city.

Margaret T. Burroughs Beach

31st Street & Lake Shore Drive in Bronzeville

This beach has some of the best skyline views of any Chicago beach. The sand area is narrow but sits next to a protected marina, with grassy areas and picnic areas above. The 31st Street Harbor marina is right there if you’re into boating or just like watching boats come and go.

Features: Small boat harbor and launch, concession stand, picnic tables, playground, fishing pier, and the Harbor Store.

Most popular with:  Water sports enthusiasts (jet ski, kayak, and paddleboard rentals are available), anglers, picnickers, and sunset watchers.

Scene: This feels more like a water activity park than a traditional sunbathing beach.

Quick facts: The harbor was part of Daniel Burnham’s original plan for Chicago and finally opened in 2012 with 300 boat slips. There’s also a large public art installation called “Windform” sculpture in the park area next to the beach.

63rd Street Beach

6300 S. Lake Shore Drive in Jackson Park/Woodlawn

This is a spacious beach with a gorgeous stone bathing pavilion that was built in 1919. The beach goes east along the lake with grass areas on the west side where families can spread out. During summer, Reggie’s sets up a stage for free weekend music shows that add a really nice community vibe.

Features: The 63rd Street Bathing Pavilion has Belly Up Jamaican concessions, showers, lockers, and meeting rooms. There are also beach chairs available, a children’s fountain and play area, a spray park, and a kayak launch.

Most popular with:  Families, culture seekers who appreciate historic architecture, and music lovers who come for the weekend shows that feature everything from reggae to blues.

Scene: Historic but community-oriented with a really friendly atmosphere. On summer days, you’ll hear great music from the stage.

Quick facts: The pavilion is a designated Chicago Landmark and was recently restored to its original beauty.

Ohio Street Beach

600 N. Lake Shore Drive in Streeterville

This is a small, hidden gem between Navy Pier and downtown Streeterville. The beach faces north, so the waters are calmer and more sheltered than most other spots along the lake. It’s small with room for maybe 50-100 people at a time.

Features: Beach chairs and umbrellas available for rent, restrooms and changing areas, lifeguard on duty during summer hours. There’s no on-site food, but Navy Pier and nearby restaurants are just a short walk away.

Most popular with:  Visitors wanting a quick, scenic stop, office workers grabbing some sun at lunch hour, swimmers who prefer calm water, and anyone looking to take some skyline photos.

Scene: Relaxed and somewhat hidden despite being right downtown.

Quick facts: This is where you want to go for the best skyline photos from beach level. The north-facing location means calm water, which is great for swimming when other beaches are choppy.

Promontory Point

55th Street & Lake Shore Drive in Hyde Park

Even though this place isn’t a traditional beach, it’s one of Chicago’s most beautiful lakefront spots. The shoreline here is rocky with smooth stone pavers, but it’s a favorite place for picnics, wading, and swimming.

Features: Benches, open lawn areas, a few BBQ grills, and basic restroom facilities. There are no concessions or formal beach rentals since this is more of a park than a beach.

Most popular with:  Couples looking for something romantic, photographers, architecture and landscape buffs, and University of Chicago students and faculty.

Scene: Calm with views of both the skyline and Lake Michigan. It’s a great place to find some peace in your day.

Quick facts: This was designed by landscape architect Alfred Caldwell in 1937 and became a designated Chicago Historic Landmark in 2020.

Making The Most Of Your Beach Day

Getting There and Parking 

Most beaches have limited and expensive parking, especially on summer weekends. The Lakefront Trail connects all the beaches and is perfect for biking if you want to avoid parking. 

CTA buses are the most convenient way to get to the beaches, and some are even walking distance from L stops. If you’re driving, arrive early in the morning or find parking in nearby neighborhoods.

Safety and Conditions 

Remember that Lake Michigan can have surprisingly strong currents and undertows, so it’s important to only stay within designated swimming areas. 

You’ll find lifeguards on duty at most beaches from Memorial Day through Labor Day, usually from 11 am to 7 pm. 

The Chicago Park District website posts daily updates on beach conditions and any closures due to high bacteria levels, so make sure to check those out before leaving for the beach.

Finding Your Beach Neighborhood

Whether you’re visiting Chicago for the summer or thinking about making this city your home, we know these lakefront neighborhoods better than anyone else.

Want to get to know the city more? Give us a shout, and we’d be happy to help you explore what each area has to offer beyond just the beautiful beaches – the restaurants, schools, transportation, and all the other factors that make a neighborhood worth calling home.

The post Best Chicago Urban Beaches To Enjoy This Summer appeared first on Ben Lalez.

School is out, and you know what that means! It’s time to make the most of our short summer months, and there’s honestly no city that does summer quite like we do.

We’re the Ben Lalez Team, and after helping over a thousand families find their perfect Chicago homes over the last decade, we’re excited to share some of our thoughts on how you can best enjoy July and August. Summer in Chicago is when the lakefront comes alive, every neighborhood has something going on, and you just want to be outside from sunrise to sunset.

Whether you’re a longtime Chicagoan looking to rediscover your city, someone thinking about making Chicago home, or just visiting for the summer, we’ve put together the ultimate bucket list for 2025. These aren’t just the obvious tourist spots (though some of those made the list because, honestly, they’re pretty great). These are the experiences that capture what makes Chicago summers special.

So grab a cold drink, settle in, and let’s talk about the 10 things you absolutely need to check out this summer in Chicago.

1. Lollapalooza (July 31 – August 3)

If you love music and big events, then Lollapalooza is a no-brainer. Grant Park transforms into music heaven for four days every summer, and it’s honestly something every Chicagoan should experience at least once.

This year’s lineup is pretty incredible. We’ve got Olivia Rodrigo and TWICE headlining the event, along with 170+ other bands across all nine stages.

If you’re thinking about going, buy tickets as quickly as possible. This thing sells out, and people come from all over the world for it. Pro tip from our years of living here – the Thursday lineup is often just as good as the weekend but way less crowded. And if you live in the South Loop or are thinking about buying there, you’ll basically be walking distance from one of the world’s biggest music festivals every summer. How incredible is that?

2. Chicago Air & Water Show (August 16-17)

The Chicago Air & Water Show is the largest free air and water exhibition in the United States, and it’s been running since 1959. Every August, fighter jets, stunt pilots, and parachute teams put on an incredible show right over the lake. There’s nothing quite like the sound of jets rumbling over the water.

North Avenue Beach is the classic viewing spot, but you can catch the action from pretty much anywhere along the lakefront. If you’re living in Lakeview, Lincoln Park, or any of the lakefront neighborhoods, this becomes your front-yard entertainment for a weekend. Just remember to bring chairs or a blanket and get there early, because this is one of those events where half the city shows up.

3. Taste of Chicago (September 5-7)

The Taste of Chicago is celebrating its 45th year in 2025, and it’s moving back to Grant Park in early September with free admission. This is Chicago’s food scene all in one place.

Expect dozens of vendors selling everything from deep dish pizza to Italian beef. There will also be incredible international cuisine that reflects all the different communities in the city. Aside from the great food, there are free concerts every evening with tons of family activities to enjoy.

This year, they’re also doing pop-up Taste events in neighborhood parks throughout the summer. Check out Pullman Park on July 19th and Albany Park on August 9th. It means you can get that Taste experience closer to home, whether you’re in Pilsen or Rogers Park or anywhere in between.

4. Chicago Jazz Festival (August 28-31)

Chicago has a long history with jazz, and the Chicago Jazz Festival over Labor Day weekend is where you can really take it all in. This free festival brings both local legends and international jazz stars to Millennium Park’s Pritzker Pavilion.

It’s the 40th annual edition this year, so you know they’re planning something special. If you’re thinking about the Loop or South Loop for your next home, events like this are basically in your backyard. Imagine being able to walk to world-class jazz performances all weekend long – it’s a jazz lover’s dream.

5. NASCAR Chicago Street Race (July 5-6)

This is NASCAR’s third year transforming downtown streets into a racetrack, and it’s still pretty wild to see stock cars racing past Chicago landmarks at crazy speeds.

The race weekend is July 5-6 this year. What makes this special isn’t just the racing – it’s seeing cars flying around Grant Park with Lake Michigan and the skyline right there. Plus, there’s live music (the Zac Brown Band is doing a post-race concert on Saturday) and family activities throughout the park.

If you’ve never seen a NASCAR race, especially one in an urban setting like this, it’s 100% worth checking out. The sensory overload in person is incredible, and it’s one of those Chicago experiences you have to cross off your bucket list.

6. Premier League Soccer at Soldier Field (July 30)

Okay, this one will be exciting for soccer fans because, for the first time ever, Chicago is hosting Premier League teams for competitive matches. On July 30, Soldier Field will have a doubleheader: Manchester United vs. AFC Bournemouth, and West Ham United vs. Everton.

We think the atmosphere is going to be electric, with passionate fans from all over the Midwest descending on Soldier Field. You don’t want to miss this.

If you’re living in the South Loop or Near South Side, you’re walking distance from what could be a historic sports event for the city.

7. Architecture River Cruise

This one might sound touristy, but it’s worth talking about. Architecture boat tours are one of those things that even longtime Chicagoans should do regularly, especially in summer.

Chicago basically invented the modern skyscraper, and seeing our architectural history from the water gives you a completely different perspective on the city. Multiple companies run these tours, from the Chicago Architecture Center’s 90-minute cruises to more casual sunset trips.

The guides on these tours know their stuff, and you’ll learn things about buildings you pass every day that you never knew. Plus, there’s something special about seeing the city from the water that makes you appreciate living here even more. We highly recommend you try this if you haven’t experienced it yet.

8. Cubs Game at Wrigley Field

Nothing says Chicago summer quite like an afternoon at Wrigley Field watching the Chicago Cubs play baseball. What makes Wrigley special isn’t just the ivy-covered walls or the hand-turned scoreboard – it’s the whole experience. The energy in Wrigleyville on game day, the tradition of singing “Take Me Out to the Ballgame” during the seventh-inning stretch, and… if the Cubs win, sticking around for “Go, Cubs, Go.” This is classic Chicago!

Even if you’re not a huge baseball fan, there’s something about spending a summer afternoon at Wrigley. And if you’re thinking about Lakeview for your next home, you’d be living in one of Chicago’s most iconic neighborhoods, walking distance from one of baseball’s most historic ballparks.

9. Navy Pier’s Summer Fireworks

From Memorial Day through Labor Day, Navy Pier puts on fireworks shows every Wednesday at 9 pm and Saturday at 10 pm. 

You don’t have to fight the crowds at Navy Pier to see them, because you can catch the show from the Riverwalk, from rooftop bars downtown, or from beaches and harbors all along the lakefront.

It’s free and it happens twice a week all summer long, so you have plenty of opportunities to make it out one night.

10. Lakefront Trail and Beaches

The 18-mile Lakefront Trail might be Chicago’s biggest source of pride. In the summer, this trail is alive with cyclists, runners, families with strollers, and people just enjoying being outside. You can rent a bike if you don’t have one. 

Along the trail, you’ll find beaches like Oak Street Beach and North Avenue Beach where you can swim, play volleyball, or just relax on the sand.

Some of the beaches even have cafes and bars – Castaways at North Avenue Beach is perfect for grabbing a drink with a view. Whether you’re exercising, relaxing, or just soaking up the sun, the lakefront is where Chicago’s summer lifestyle can be most enjoyed.

Making the Most of Summer in Chicago

Here’s what we’ve learned after years of living here and helping families find their perfect Chicago neighborhoods: summer is when this city really shows off. The festivals, the lakefront, the outdoor dining, the energy – it all reminds us why people fall in love with Chicago.

Whether you’re already living here or thinking about it, make sure you get out and experience what makes Chicago summers so special. After all, we spend enough time indoors during our winters. Summer is when we make up for it and let loose!

Ready to explore these neighborhoods and maybe find your perfect Chicago home? Give us a shout, we’d love to show you around and help you discover which part of this amazing city could be your home base for all these incredible summer experiences!

The post 10 Must-Do Summer Things In Chicago (2025 Bucket List) appeared first on Ben Lalez.

Last year, we wrote an article on the top 10 suburbs in Chicago, and this year we’re back with our updated list for 2026. Have things changed on the list?

In case this is the first time you’re reading one of our articles, we’re the Ben Lalez Team, and we’ve helped over a thousand families find homes in and around Chicago over the past decade. Every year around this time, our team looks ahead to see where buyers should be looking.

The biggest change from a year ago is mortgage rates. The 30-year fixed was around 6.76% at the start of 2025. By late February 2026, it was at 5.98%. On a $450,000 home with 20% down, that works out to roughly $170-$200 less per month.

Without further delay, let’s get into the list!

1. Naperville

Naperville is the largest suburb on this list, with a population of around 150,000. The downtown has restaurants, shops, and the Riverwalk, which runs about 1.75 miles along the DuPage River through the center of town.

Median prices are around $600,000, essentially flat from last year. There are typically 270+ homes on the market at any given time, with roughly 60-65 new listings coming in per month. Homes are averaging about 71 days on market.

ACS data puts the average monthly owner costs with a mortgage in Naperville at around $3,150 (this includes taxes and insurance). If you’re thinking about Naperville, make sure to run the math before you set your price ceiling.

Districts 203 and 204 are among the best school districts in Illinois. We’ve previously written about the best school districts in Chicago. District 203 covers most of central and north Naperville and feeds into Naperville Central. District 204 covers the south and west portions and feeds into Naperville North. Both are good, but they’re different attendance zones and different neighborhoods, so know which one you’re buying into.

The BNSF Metra line has two Naperville stations: Naperville and Route 59, with both running into Union Station. Express trips take about 35-45 minutes, depending on your stop and time of day.

2. Downers Grove

The Tivoli Theater has been running since 1928. You’ll find Saturday morning farmers market running from spring through fall. There are restaurants with outdoor seating in warm weather, and it’s a small-city downtown feel built around the Metra station. There are two BNSF stations here (Main Street and Fairview Avenue), and express trains to Chicago take about 30 minutes.

Median prices in Downers Grove are around $580,000, with homes selling in about 59 days, faster than last year. Current home inventory runs 90-100 active listings with around 30 new listings coming on per month.

District 58 covers K-8, and District 99 covers the high schools (Downers Grove North and Downers Grove South), with both having solid programs. Downers Grove also sits at the intersection of I-88 and I-355, which is convenient if your commute is by car to the East-West corporate corridor rather than by train into the city.

3. Oak Park

Oak Park is directly west of Chicago’s Austin neighborhood, about 10 miles from the Loop. The Metra UP-W has two stations here, Oak Park and Ridgeland, with trips to Ogilvie running 16 to 23 minutes. The CTA Green and Blue lines are also there. Just note that parking at the L stops is pretty limited.

Frank Lloyd Wright’s home and studio are here, along with about 25 homes he designed within walking distance. Marion Street and Lake Street downtown have restaurants, coffee shops, and independent retail. There are Thursday farmers market, summer arts festivals, and a fairly active community event calendar throughout the year.

Median prices are around $380,000. Homes are selling in about 52 days. Inventory typically runs 50-55 active listings.

4. Evanston

Evanston sits on the lakefront directly north of Chicago. Northwestern University has been here since 1855. There are beaches, parks, a real downtown, and a food scene that covers everything from casual to special-occasion.

The Metra UP-N line runs from Davis Street station to Ogilvie in about 26 minutes. The CTA Purple Line is also there with stops throughout the city.

Median prices are around $476,000, up about 6% from last year. About 85 active listings at any given time, with roughly 33 new listings per month. Homes are currently selling in about 56 days.

Evanston’s housing mix is fairly wide. Lakefront blocks have historic single-family homes, and downtown you’ll see condos above restaurants. There are quiet residential streets and dense apartment corridors. The experience varies significantly by neighborhood, so it’s worth exploring a few different areas before you narrow down a price range.

5. Arlington Heights

Median prices in Arlington Heights are around $495,000, down slightly from last year. Homes are selling in about 51 days, which is down from 72 days last year, and inventory stands at 62 active listings with 26 new listings per month.

The downtown around the Metra station has been adding restaurants and activity over the past several years. The old Arlington Park racecourse site is in active redevelopment. The village approved a mixed-use plan that includes housing, retail, and public space. That project will take years to build out, but it’s approved and in motion.

The UP-NW Metra line serves Arlington Heights, with travel time to Ogilvie running about 45-55 minutes.

District 214 serves the high schools in this area, including Buffalo Grove HS, Rolling Meadows HS, and Hersey HS, which is consistently among the top-performing districts in Illinois. Median household income in Arlington Heights is around $116,700. The park system here is extensive, with over 50 parks and facilities.

6. Buffalo Grove

FBI data shows 9 reported violent crimes in Buffalo Grove in 2024. That’s the total count, not a rate. It’s one of the lowest figures in the entire Chicago metro area.

Median prices are around $425,000, up significantly from last year. Inventory is thin, with about 34 active listings and 16 new listings per month. When well-priced homes come on the market, they tend to move quickly. For the rest of home in this area, they’re averaging about 65 days on market.

Buffalo Grove has a notably diverse population, with a large South Asian and Eastern European community that has grown here over the past few decades. That shows up in the restaurants, school programs, and community events.

Parts of Buffalo Grove feed into Stevenson High School in Lincolnshire, which consistently ranks among the top public high schools in Illinois. The rest of the village belongs to  Buffalo Grove High School. The median household income here is around $129,400.

Transit is the NCS Metra line, North Central Service, with two stations in town. Travel time to Union Station runs about 58 minutes. The NCS runs less frequently than the BNSF or UP lines, so check the full schedule to get an idea of your commute times.

7. La Grange

La Grange has two BNSF stations, LaGrange Road and Stone Avenue, with scheduled travel times to Union Station in the 20-30 minute range. A lot of homes in La Grange are within a short walk of the downtown and the train.

What’s it like living here? The Pet Parade has been running annually since 1946. You’ll find summer arts festivals, holiday events, independent shops and restaurants around the train station. It’s a small town that’s stayed a small town despite being 15 miles from the Loop.

Looking at pricing, the January data in La Grange was distorted this year. There wasn’t a lot of inventory, and that means a handful of transactions can skew a single month’s median in either direction. ACS data puts median owner-occupied home values around $594,300, which is more in line with what actually trades in the village. La Grange is considered a premium market.

Inventory is low right now, with around 22 active listings and 11 new listings per month. LTHS holds a Commendable designation on the Illinois School Report Card. The median household income in La Grange is around $159,900, the highest on this list.

8. Park Ridge

Park Ridge sits on Chicago’s northwest border. The Metra UP-NW line runs from Park Ridge station to Ogilvie in about 32 minutes, and O’Hare Airport is about 5 miles away.

The downtown area is called Uptown. Park Ridge is made up of local restaurants, shops, and well-maintained residential streets that are mostly single-family homes, a mix of older construction and renovated properties.

Median prices are around $577,000, up modestly from last year. We’ve seen some movement in this area, with homes selling in about 32 days right now, down from 62 days last year. Current inventory is around 48 active listings with 18 new listings per month.

9. Orland Park

Orland Park is a southwest suburb, about 25 miles from the Loop. Getting into downtown Chicago by car takes 45 minutes to over an hour, depending on traffic and time of day. The Metra Rock Island and SWS lines serve parts of the area.

Median prices are around $372,500, up about 6% from last year, and homes are selling in about 53 days. There are about 117 active listings at the moment, more than any suburb on this list (except Naperville), with roughly 27 new listings per month.

Carl Sandburg High School is in Orland Park and regularly ranks among Illinois’ top public high schools. The village has over 60 parks and miles of bike trails. The median household income in Orland Park is around $98,900.

10. Wheaton

Wheaton is in DuPage County, about 25 miles west of the Loop. The UP-W Metra line runs from Wheaton Station to Ogilvie in about 53 minutes.

Downtown Wheaton has coffee shops, restaurants, and the French Market on Saturdays. The Illinois Prairie Path runs through the area: it’s a converted rail corridor with miles of paved trails connecting across DuPage County. You can cover a lot of ground without crossing a major road.

Median prices are around $410,000, up about 21% from last year, though some of that reflects month-to-month variation. Homes are selling in about 59 days, and the current inventory is around 46 active listings.

The median household income is around $120,000. Community Unit School District 200 covers pre-K through 12 and includes Wheaton North and Wheaton Warrenville South high schools, both well-regarded.

There You Go!

So there you have it, our take on the top 10 Chicago suburbs for buyers heading into 2026.

Each one made this list for different reasons, and if you’re seriously considering which one is the right fit for you, you’ll have to think about what you’re prioritizing: commute time, budget, schools, walkability, and space. We spend a lot of time in these neighborhoods, and we’re happy to talk through any of this in more detail.

Please note that the data we’ve provided in this article is a reflection of the market at the time of writing this article. If you want updated data on any of these areas, let us know and we’ll be happy to provide you with detailed reports. Give us a shout anytime. 

And if you’re buying for the first time, don’t forget to grab our Chicago Home Buying Guide. It covers everything from making an offer to what happens at the closing table!

Until then, see you next week for our next article.

The post Top 10 Chicago Suburbs For Buyers In 2026 appeared first on Ben Lalez.

We’re the Ben Lalez Team, and after helping over a thousand families find their perfect Chicago homes over the last decade, we’ve heard everything there is to know about the Windy City.

Today, we’re sharing an honest look at what makes Chicago an amazing place to call home, and what might make you think twice. There won’t be any sugar-coating here. Just real talk from locals who know this city inside and out.

Let’s get into our top 5 reasons to make the move, and the top 5 reasons why you might want to reconsider.

5 Reasons To Move To Chicago

1. A Neighborhood For Every Personality

Chicago isn’t just one city. It’s more fondly known for it’s 77 neighborhoods, and each one has its own character and community vibe. 

For example, in River North you can feel the hustle and bustle, and in Lincoln Park you’ll enjoy the tree-lined streets. If you have an artistic spirit, give Wicker Park a visit. And if you’re a lakefront type of person, then Lakeview is the spot you want to check out.

Each neighborhood gives you a different experience, which means that with a little bit of research and exploration, you can find exactly what fits your lifestyle. We promise there’s a perfect Chicago neighborhood waiting for you.

2. World-Class Culture But Still Affordable

Chicago is a cultural powerhouse. You’ll find renowned museums like the Art Institute and Field Museum and an incredible theater scene. If you’re a music lover, there are music venues that host everything from jazz and blues to all of your favorite concerts.

Are you a foodie? Because you’ll find a world-class food scene in the city, from small and intimate diners to Michelin-starred restaurants. And if you love outdoor events, Chicago is a city of festivals. There are charming neighborhood street fests, and massive events like Lollapalooza and the Chicago Jazz Festival. Whichever types of festivals you like attending, Chicago has them all.

The best part is that you can enjoy all this at a fraction of the cost of New York or Los Angeles.

3. Real Estate Prices That Give You More For Your Dollar

When it comes to housing affordability, your budget stretches much further in Chicago than in other major cities around the U.S.

The average median home price in Chicago is around $355,000. Compare that to nearly $750,000 in Boston and over $970,000 in Los Angeles, and you’ll get a better sense of just how affordable Chicago can be. This means with the same budget, you can get more space, better finishes, and maybe even that yard you’ve been dreaming about.

The real estate market in Chicago is also incredibly diverse, offering all kinds of property types. From historic bungalows and classic greystones to modern condos and converted lofts, there are plenty of fantastic options for everyone.

4. Getting Around Is Convenient

One of Chicago’s best features is its public transportation system. The “L” trains and vast bus network make it easy to get around the city without owning a car.

The city’s grid system makes the system easy to figure out, and most neighborhoods are highly walkable. During the warmer months, the lakefront trail and growing network of bike lanes make cycling a great option too.

If you’re planning a weekend road trip, Chicago is close to lots of nearby towns. You have access to beautiful state parks and even neighboring big cities that are all within a few hours’ drive. You won’t have to drive further than a couple of hours if you want to explore more of what the Midwest has to offer.

5. Four Seasons Of Fun

Yes, Chicago winters are famous (more on that later), but having four distinct seasons means four climates where you can enjoy different activities.

In the summer, you can enjoy 26 miles of lakefront, outdoor dining, and parks filled with free concerts and movies. In the fall, you’ll get gorgeous autumn colors and crisp sweater weather to take some of your best Instagram photos. Winter has its own charm with ice skating and holiday markets. And of course, spring is when we all celebrate that winter has finally passed!

5 Reasons To Think Twice About Moving To Chicago

1. Winter Is A Big Drag

We need to talk about winter. Chicago’s winters aren’t just cold. They’re an entire lifestyle adjustment.

December through March means you’ll be dealing with freezing temperatures and lakefront winds that cut right through your bones. It takes a special kind of mental toughness to handle the wind chill when it hits negative numbers.

Daily life gets more inconvenient in the winter. You’ll have to deal with warming up your car, snow-covered sidewalks, and the infamous “dibs” system for parking spaces. Want to learn more about what dibs are, along with other surprising facts about life in Chicago for first-timers? 

Winter is not for everyone, but it’s manageable. If you’re a person who deals with seasonal depression, winter in Chicago can seem like it drags on forever.

2. Higher Property Taxes

One thing that surprises a lot of people is that Chicago’s property taxes are significantly higher than the national average.

In Cook County, the effective tax rate is about 2% of your home’s value. That means on a $300,000 home, you’d be paying roughly $6,000 a year in property taxes. That’s essentially double the national average and much higher than what you’d pay in many other cities. We’ve written before about how to calculate your Chicago property taxes, so make sure to check out that article.

The property tax system in Chicago can be complicated, with various exemptions that can help save you some money if you know how to find them and use them. And because reassessments happen every three years, your tax bill can change significantly over time. 

3. Big City Problems

Like any major city, Chicago has its big city challenges. Traffic can be pretty terrible during rush hours. Finding parking in popular neighborhoods might have you questioning your life choices. Commuting in a car can definitely test your patience.

You’ll find crime in some areas, but it varies depending on the neighborhood. We’re a big city, so some parts feel completely different from others when it comes to safety and city services.

Dealing with the city can be frustrating sometimes too. Getting permits for home improvements and dealing with Chicago-specific regulations will take time and preparation.

4. The Cost Of City Living Adds Up

Although Chicago is more affordable than other coastal cities, it’s still pricier than many other cities in the Midwest. Aside from housing costs, there are other expenses to consider.

Chicago’s sales tax is among the highest in the country at 10.25%. You’ll also find car insurance rates much higher than the national average.

If you’re buying a condo, you’ll have to pay HOA fees and that adds to your monthly housing costs.

And if you own a car, city stickers, parking permits, and occasional parking tickets is something you’ll have to deal with regularly.

5. It Takes Time To Really Feel At Home In Chicago

Feeling like a true Chicagoan will take you some time. The city has its own way of doing things and its own language. For example, we never call it the subway, we call it “The L.”

If you’re trying to meet people and build up a circle of friends, it can be tough, especially if you’re moving from a smaller community. Chicago neighborhoods can sometimes feel like separate towns with their own community cultures and vibes. This is just normal in big city life.

This also means that it takes time to really get to know your way around and find your favorite spots. And figuring out which neighborhood truly fits your lifestyle might involve some trial and error, but you’ll have fun exploring.

The Bottom Line

Chicago really has a lot to offer. 

While it might not be for everyone, the city offers both big-city amenities and Midwestern friendliness with its own character. It is something that will definitely grow on you.

We recommend coming in with realistic expectations. Understand the challenges, but also look for the amazing opportunities that come with living in Chicago. 

Try talking to people who live here. And if possible, visit Chicago at different times of the year and explore all the different neighborhoods before making your decision.

Whether you decide Chicago is right for you or not, we’re always happy to grab a coffee with you and share our insights. Contact us if you’d like to learn more about specific neighborhoods, or what it’s really like to live here.

The best decisions are informed ones, and we’re here to help you figure out if Chicago should be your next home!

The post 10 Reasons You Should (Or Shouldn’t) Move to Chicago appeared first on Ben Lalez.

Everyone feels overwhelmed by the financial commitment because it’s a lot of money to spend on one thing. Plus, there’s the question of whether to stay in the city or explore the surrounding suburbs.

But don’t worry, the Ben Lalez Team has your back! We’ve helped over a thousand families move homes over the last decade, so we’re very passionate about real estate in Chicago and its suburbs.

So which suburbs should you consider in 2025? Here’s our honest take on the top 10 suburbs that offer good value, great communities, and that special something that makes a place feel like home.

1. Naperville

Naperville keeps showing up on “best places to live” lists for good reason. The Riverwalk is gorgeous and gives the downtown a unique feel you just don’t find in most suburbs.

The community here is strong. You’ll notice it right away when you visit the local restaurants, shops, and summer festivals. Everywhere feels buzzing with activity, but not in an overwhelming way.

While we could talk about the excellent schools (Districts 203 and 204 rank among Illinois’ best) or the convenient Metra BNSF line, what our clients actually fall in love with is the lifestyle. You get plenty of space and safety while still having tons to do on weekends without driving into the city.

Homes here do sell for more than some other suburbs (median price around $523,000), and the average days on market is 44 days. This tells us buyers recognize the value despite the higher price point.

2. Downers Grove

Downtown Downers Grove just clicks with people. The historic Tivoli Theater still shows movies. Local restaurants have patios filled with people enjoying dinner on summer evenings. The farmers market brings everyone out on weekend mornings.

The community here is super friendly. Neighbors actually talk to each other. Block parties happen regularly. Kids ride bikes between houses. It’s that neighborhood feel that many people miss from their own childhoods.

For commuters, Downers Grove sits on the BNSF Metra line with express trains reaching Chicago in about 30 minutes. But honestly, many residents find themselves heading into the city less often than they expected because there’s so much to enjoy locally.

Homes here sell for around $469,000 median price, and they typically stay on market for just over 50 days. This gives buyers some breathing room to make decisions without the crazy competition of hotter markets.

3. Oak Park

Oak Park is special. There’s just no other way to put it. Sitting right next to Chicago’s west side, it feels like a small town with big city access.

Architecture buffs love Oak Park for Frank Lloyd Wright’s influence. His studio is here, along with many homes he designed. But there’s so much more to the community than just great buildings.

The streets are packed with small businesses that have real character. Bookstores where the owners recommend their favorite reads. Coffee shops where they remember your order. Restaurants where the chef might stop by your table. It feels personal in a way many places don’t anymore.

Events happen year-round. Art festivals take over the streets in summer. Farmers markets run weekly. Holiday festivals bring everyone out in winter. There’s always something happening that brings the community together.

Transit couldn’t be easier. Both CTA and Metra serve Oak Park, putting downtown just 20 minutes away. Many people walk to stations since the community is very walkable.

Homes here sell for about $430,000 median price, which gets you way more space and character than the same money in Chicago. For the location and community, it’s a pretty good deal.

4. Evanston

Evanston is Chicago’s cool northern neighbor. With Northwestern University anchoring the community, it has energy you don’t find in most suburbs.

The food scene here is amazing. From cheap eats to special occasion restaurants, Evanston has it all. The lakefront adds another dimension with beaches and parks that make summer weekends feel like vacation.

What’s cool about Evanston is how different areas have different vibes. The lakefront has historic mansions. Downtown has modern condos. There are quiet tree-lined streets with single-family homes and bustling areas with apartments above shops. You can find your fit here.

Getting downtown is simple with both CTA and Metra options taking about 25 minutes. But many Evanston residents find they don’t head to Chicago as often as they thought they would. There’s just too much good stuff happening locally.

The housing market is steady with median prices around $431,000 and homes typically selling in about 38 days. This shows strong demand without the pressure-cooker feel of some markets.

5. Arlington Heights

Arlington Heights has really come into its own in recent years. The downtown area around the Metra station has transformed from sleepy to exciting.

The restaurant scene keeps growing with everything from casual spots to nice date-night options. The entertainment options include live music venues and summer festivals. The village puts real effort into creating community events that bring people together.

Everyone’s talking about what’s happening with the old Arlington Park racecourse property. The massive redevelopment will bring even more options to the area in coming years. The village is forward-thinking about how to grow while keeping its character.

Schools are excellent (District 214 consistently ranks among Illinois’ best), but most families we work with are equally excited about the park system and recreation opportunities. There’s a good balance of organized activities and natural spaces.

Homes in Arlington Heights sell for a median price of about $500,000, typically moving in around 48 days. This price point gets you significantly more space than in Chicago while staying in a community with plenty going on.

6. Buffalo Grove

Buffalo Grove is where your dollar stretches further. The homes are generally newer than in some other suburbs, often with more modern layouts and features that today’s buyers want.

What makes this community stand out is its diversity. Buffalo Grove welcomes everyone, creating a rich community where different cultures and traditions are celebrated. This shows up in local restaurants, community events, and the overall welcoming vibe.

While there’s no traditional downtown, Buffalo Grove makes up for it with amazing parks and recreation facilities. The Buffalo Grove Park District runs top-notch programs for all ages. The extensive bike paths and green spaces make outdoor living easy.

Schools perform well above state averages. Parts of Buffalo Grove feed into Stevenson High School, one of Illinois’ best, while Buffalo Grove High School itself has strong programs and outcomes.

Here’s the best part – the median home price is about $360,000, making Buffalo Grove one of the most affordable options on our list. Homes typically sell in just over two months, giving buyers more time to consider options than in some faster markets.

7. La Grange

La Grange feels like small-town America dropped right into the Chicago suburbs. The downtown area has that Main Street charm that’s hard to find these days.

Local shops line the streets around the Metra station. The historic Tivoli Theater still draws crowds. Restaurants have sidewalk seating in warm weather. Ice cream shops have lines out the door on summer evenings. It just feels right.

The community really comes together for events like the Pet Parade, summer arts festivals, and holiday celebrations. These aren’t just things on a calendar – they’re traditions that families look forward to year after year.

Many homes are within walking distance of downtown, which creates a true neighborhood feel. Kids can bike to get ice cream. Parents can walk to dinner. It’s the kind of lifestyle that makes suburban living appealing.

La Grange homes sell for a median price of about $440,000, typically moving in around 6 weeks. This strong demand shows how much people value the community La Grange has created.

8. Park Ridge

Park Ridge sits right at Chicago’s northwestern edge, giving you that suburban feel with city convenience. This is Hillary Clinton’s hometown, and it still has that classic American neighborhood vibe.

The downtown area (they call it “Uptown”) has been beautifully developed with local restaurants, shops, and the iconic Pickwick Theatre. On nice evenings, it feels like the whole town is out enjoying the area.

The neighborhoods here are gorgeous. Tree-lined streets feature a mix of historic homes and newer construction, all impeccably maintained. People take real pride in their properties and it shows when you drive around.

Location is a huge selling point. Park Ridge borders Chicago, and the Metra UP-NW line gets you downtown in about 30 minutes. O’Hare is nearby too, which is perfect for frequent travelers or those working at the airport.

Homes in Park Ridge sell for a median price of about $530,000, typically moving in under two months. This price reflects the premium location and quality of life, but it’s still reasonable compared to some North Shore communities.

9. Orland Park

Orland Park gives you room to breathe. This southwest suburb offers larger lots, bigger homes, and more space than you’ll find closer to the city.

The lifestyle here is comfortable. Streets are wider, traffic is lighter, and parking is plentiful. You don’t have to fight crowds to enjoy shopping at Orland Square Mall or dining at the many restaurants.

Outdoor spaces are a big plus. With over 60 parks, miles of bike trails, and beautiful forest preserves nearby, getting outside is easy. The village runs great recreation programs with activities for everyone from toddlers to seniors.

Schools perform well above state averages, with Carl Sandburg High School consistently ranking among Illinois’ best public high schools. This makes Orland Park popular with families looking for quality education.

The real highlight is affordability. The median home price in Orland Park is just $337,000, one of the lowest on our list. Homes take longer to sell here (almost 3 months on average), which means buyers can take their time and have more choices.

10. Wheaton

Wheaton might surprise you with its personality and charm.

Having Wheaton College in town makes a big difference. It brings cultural events, youthful energy, and a certain intellectual vibe to the community. The downtown area feels alive with students and locals mixing at coffee shops, restaurants, and the popular French Market on Saturdays.

One thing that stands out is the Illinois Prairie Path running through town. This converted rail line gives miles of paved trails for biking, running, or walking. You can go for hours without crossing a major road. It’s perfect for active families.

The community hosts events year-round that bring people together. Summer concerts, art festivals, holiday celebrations – there’s always something happening that makes it easy to meet neighbors and feel connected.

Housing prices are surprisingly reasonable given all Wheaton offers. The median price is about $360,000, which can get you anything from a starter condo to a spacious family home depending on your needs. This accessibility makes Wheaton great for first-time buyers and growing families alike.

Making Your Move

If you’re thinking about leaving the city for more space, you’re not alone. Every year, we help dozens of families find their perfect suburban match.

Each suburb on this list offers something different. What matters most is finding the place that fits your lifestyle, budget, and needs. Some people want a lively downtown, others prioritize outdoor space or schools or commute time.

The good news is that Chicago’s suburbs offer incredible variety and value compared to many other major metro areas. You can find your perfect fit without compromising what matters most to you.

Ready to explore these communities? Give us a shout and let’s explore which Chicago suburb might be right for you! And if you’re buying for the first time, make sure to download our Chicago Home Buying Guide.

The post Top 10 Chicago Suburbs For Homebuyers 2025 appeared first on Ben Lalez.

We’re the Ben Lalez Team, and after helping over a thousand families find their perfect Chicago homes over the last decade, we’ve noticed a growing interest in co-ops. They offer some advantages that many buyers overlook, so let’s check out what makes co-ops special and why they might be worth considering when you’re looking for your next home.

What Is A Co-op?

When you buy a regular condo, you own the property. But when you buy a co-op, you’re actually buying shares of the corporation that owns the entire building. Your shares then give you the exclusive right to live there and have voting rights when decisions need to be made about the building.

This ownership structure creates some interesting differences that can work in your favor, especially in certain Chicago neighborhoods.

The Financial Advantages You Might Not Know

If budget is important to you, the biggest advantage is that co-op apartments in Chicago are generally cheaper than condos. We’ve found that similar-sized co-ops can sell for 10-20% less than comparable condos in the same neighborhood. This means a lower entry price for you if you want to get into a specific neighborhood.

Co-ops also have different fee structures than condos. Monthly assessments in co-ops look more expensive on paper, and are usually higher than condo HOA fees, but this isn’t a simple comparison. 

This is because o-op fees usually include property taxes and sometimes portions of the building’s mortgage, while condo owners pay these separately. When you calculate the total cost of ownership, the numbers become more comparable.

When it comes to financing rates, co-op boards can often refinance the entire building’s mortgage at once, potentially securing better rates than individual buyers could get on their own.

Co-Op Community 

One thing we’ve noticed over the years is that co-op buildings often have stronger community bonds. In order to purchase a co-op, buyers typically have to go through a more rigorous approval process. This means that co-op buildings tend to have lower turnover, leading to longer-term neighbors who get to know each other.

Many co-ops have active social calendars with holiday parties, summer gatherings, and community events that create that old-school Chicago neighborhood feel, even if you’re living in a multi-unit building. If you’re looking for a strong community within a building, a co-op might be perfect for you.

The Screening Process

Co-ops are known for their thorough vetting process. This might seem intimidating, but think of it from another angle. It means all your neighbors have also gone through the same careful screening.

Unlike condo associations, co-op boards have the power to decide whether or not they approve a buyer. This means purchasers will typically require extensive financial information, personal references, and often an in-person interview before being approved.

This process generally results in more financially stable neighbors, fewer rental units, and more engaged owners who care about maintaining the building’s value and maintaining a strong community.

Chicago’s Most Notable Co-op Buildings

Chicago actually has some magnificent co-op buildings with fascinating histories. The famous 1500 N. Lake Shore Drive building, designed in the 1920s, is one of the city’s most prestigious addresses. Many of the historic co-op buildings were designed by renowned architects in styles that are no longer commonly found in modern condo designs.

What’s interesting is how these buildings survived different real estate cycles. During the 2008 housing crisis, many co-op buildings in Chicago maintained their values better than comparable condos. While condo foreclosures jumped during this period (increasing from 12% to 19% of all Chicago-area foreclosures between 2007 and 2008), co-ops saw far fewer distress sales, thanks to their stricter purchase requirements and financially stronger ownership base.

Tax Considerations For Co-op Owners

As a co-op shareholder, you can still deduct your portion of the building’s real estate taxes and mortgage interest on your personal tax return, similar to other homeowners.

What’s different is how property tax assessments work. In Chicago, older co-op buildings often benefit from lower property tax assessments compared to newer condos. Co-ops are assessed as a single property (like an apartment building), and this assessment can be relatively low compared to the building’s true market value.

This tax advantage can turn into meaningful savings over time, especially in a city where property tax increases have become a big concern for homeowners.

The Maintenance Advantage

One important benefit of co-op living is how maintenance is done. Many larger Chicago co-ops have full-time maintenance personnel, often including live-in superintendents or building engineers.

For example, the Gold Coast co-op at 1242 N. Lake Shore Drive has 24-hour door staff, elevator operators, and a live-in superintendent. This offers immediate attention to building maintenance issues and creates a level of service that’s hard to find in most condo buildings.

Co-op boards are usually more proactive when it comes to maintenance, focusing on preservation rather than dealing with problems when they pop up. This can mean fewer emergency repairs and more thoughtful long-term planning for major systems.

Understanding Co-op Governance

Unlike condo associations that operate under Illinois condominium law, co-ops are more like private corporations.

This gives co-op boards more flexibility in some ways, including:

• The ability to set more comprehensive house rules
• Greater control over who buys in the building
• More options for handling problem residents
• Flexibility in how they structure their financing

If you’re a buyer who values stability and careful management, this model can provide peace of mind that the building will maintain its quality and character over time.

Making The Co-op Buying Process Smooth

We want to be clear. Buying a co-op requires a different approach than purchasing a condo or single-family home. The timeline is typically longer, and this is why it’s important to work with realtors who understand the nuances of co-op transactions.

Having helped many clients through successful co-op purchases, we’ve developed relationships with co-op-friendly lenders, attorneys specializing in co-op transactions, and even board members at various buildings. This expertise can make the difference between a stressful experience and a smooth transition to your new home.

If co-op living sounds right for you, we recommend getting pre-qualified with a lender who regularly handles co-op financing before you even start looking at units. This gives you a clear picture of your budget and strengthens your position when applying for board approval.

Is A Co-op Right for You?

We’ve found that the right home type depends entirely on your specific situation and goals. Co-ops aren’t for everyone, but for the right buyer, they can offer exceptional value, character, and community.

If you’re curious about co-op buildings, give the Ben Lalez Team a shout! We know which buildings have the best reputations, reasonable financial requirements, and most desirable locations across the city.

After all, our job isn’t just about helping you buy a property. It’s about finding you the perfect home that fits your lifestyle, in a community you’ll love. And sometimes, that perfect match might be a co-op that most buyers never even consider!

The post The Advantages Of Buying A Co-op in Chicago appeared first on Ben Lalez.

We’re the Ben Lalez Team, and we’re here to tell you that the market isn’t just one single story. It’s multiple stories happening at the same time across all 77 unique neighborhoods in Chicago.

So let’s have a quick breakdown of what’s actually happening in Chicago right now. We’re not talking about national trends or clickbait headlines. Just real numbers that give you something to work with.

We’ll cover what’s happened over the past 12 months, so grab a cup of coffee and let’s dive in!

A Market Of Three Different Performers

Let’s first divide the market into three segments (for reference, this data is taken from Zillow’s housing data). We have the Top-Tier homes (homes values within the 65th to 95th percentile range), Bottom-Tier homes (5th to 35th Percentile range), and the Middle-Tier homes (35th to 65th percentile range).

Since 2000, all three markets have performed similarly, but with wider swings and different measures of volatility.

Historical data is useful to see where we’ve come over a long period of time, but what we want to do is look at what’s happened over the last 12 months to see the current state of the Chicago real estate market:

Here’s what the data shows:

• Bottom-Tier Homes:Up 4.14%
• Middle-Tier Homes: Up 2.81%
• Top-Tier Homes: Up 2.71%

What does this tell us?

The strongest demand is currently at the entry level. First-time homebuyers and investors are competing in the affordable segment and driving stronger price growth. Meanwhile, the luxury market is still growing, just at a reserved pace.

This pattern makes Chicago a little different from many other coastal markets where luxury properties are currently outpacing other segments. Here in our city, working-class neighborhoods and starter homes are showing the most momentum.

The Biggest Neighborhood Movers

When we look at the data a little more carefully, the results might surprise you. Some of Chicago’s historically overlooked areas are now seeing strong price movement. Here is the price movement when we compare prices from March 2025 to March 2024:

• Park Manor: Up 10.89%
• The Bush: Up 10.30%
• Avalon Park: Up 9.98%
• Fuller Park: Up 9.4%
• Englewood: Up 9.3%

What’s the pattern? The South and West Sides are leading the charge. After years of underinvestment, these areas are seeing renewed interest from both homebuyers and developers looking for value and potential.

The Biggest Neighborhood Losers

There are areas in Chicago that haven’t doing so well over the last year:

• Greektown: Down 12.67%
• Ford City: Down 6.55%
• Chinatown: Down 5.33%
• Near West Side: Down 4.47%
• South Loop: Down 4.11%

Why are these areas down? Many of these areas saw big jumps during the pandemic as buyers went after more space and amenities. What we see now isn’t so much a crash as a natural correction. The South Loop and Near West Side saw a lot of development over recent years, and supply may have temporarily outpaced demand.

These areas are still maintaining high values – they’re just taking a breather after some prolonged growth.

The Geographic Divide

An interesting pattern we’ve noticed is where specifically growth is happening. Traditionally, North Side neighborhoods demonstrated the highest values and strongest appreciation, but now we see the momentum shifting:

• South Side: Multiple neighborhoods showing 7-10% growth
• Southwest Side: Areas like Brighton Park (8.27%) and Marquette Park (8.80%) are doing well
• West Side: Neighborhoods like Little Village (9.62%) and South Austin (8.37%) are seeing strong gains

On the other hand, many North Side areas are seeing more measured growth:

• Lincoln Park: Up 4.58%
• Lake View: up 5.19%
• Wicker Park: Up 3.06%
• Logan Square: Up just 1.35%

Maybe this is signalling a rebalancing of Chicago’s real estate values across the city, with historically undervalued areas catching up with established neighborhoods?

What These Numbers Mean For Buyers

First-Time Home Buyer

You’re in the quickest moving segment right now, especially in areas like South and West Side neighborhoods. You might need to move quickly on some desirable listings, so be prepared.

Move-Up Buyers

The Middle-Tier segment gives you a bit more breathing room. With growth of 2.81%, these homes are appreciating at a healthy pace. You’ll have more negotiating power than entry-level buyers.

Luxury Buyers

With the luxury segment growing at 2.71%, you’ll likely have more negotiating leverage. Some high-end neighborhoods like Bucktown (-0.39%) and River North (-1.56%) are even seeing slight declines, which could create some opportunities for you.

What Else We’re Seeing On The Ground

It’s useful to look at statistics, but it’s also important to take in some more context:

• Mortgage rate sensitivity remains high: Even small rate movements can significantly impact buyer demand and affordability. With uncertainty on which direction the rates will go, we’re keeping our eye on this.
• Property condition matters more than ever: Today’s buyers are less willing to take on major renovation projects. Move-in ready homes are fetching premium prices.
• Neighborhood amenities drive decisions: Buyers want access to parks, quality schools, restaurants, and transit access.
• Generational shifts: Millennial and Gen Z buyers are prioritizing features different from those of their parents, with walkability, energy efficiency, and smart home features in demand more than ever.

A Complete Breakdown Of Price Movement In Every Chicago Neighborhood

Here’s the entire list of home value differences based on values from March 2025 compared to March 2024:

The Bottom Line

Chicago’s real estate market so far in 2025 is healthy but varied. Understanding which segment you’re looking at can help you develop realistic expectations.

Whether you’re buying or selling, the key is to grasp neighborhood-specific knowledge so you can make data-driven decisions. The days of one-size-fits-all advice are far behind us.

And that’s exactly why working with a team that understands Chicago at the neighborhood level makes all the difference. We’re deeply connected to what’s happening across the city, and after a decade of helping over a thousand families change homes, we’re always ready to help you.

Want to know what any of these data points mean for your specific situation? Get us to call you, and let’s chat about your real estate goals. No pressure – just insights and friendly advice from neighbors who know this city inside and out.

The post Chicago Real Estate Market Snapshot April 2025 appeared first on Ben Lalez.

The Midwest is filled with hidden gems, charming towns, and a bunch of natural wonders. And they’re all within a reasonable drive from the city. In this guide, we’ve found the best places to take your family on a road trip, all within a 4.5 hour drive from Chicago. 

That means if you leave in the morning, you’ll make it in time for lunch somewhere new! Whether that’s another big city in a neighboring state or a charming smaller town along the way, you’ll find lots to do and discover that will give you lots to talk about on the drive back home.

Join the Ben Lalez Team and let’s look at all the best road trips you can take from Chicago.

Big City Adventures

Milwaukee, Wisconsin (1.5 hours)

Milwaukee feels like a smaller and more relaxed Chicago. You can check out places like the Milwaukee County Zoo, the art museum right on the lake, or you can tour a brewery. The downtown area is very walkable, and parking is much cheaper than in Chicago.

Indianapolis, Indiana (3 hours)

This is another city with a very walkable downtown. You’ll find The Children’s Museum, which is the largest in the world and worth the trip alone. White River State Park connects most major attractions, and you can spend a day at the zoo or catch a Colts or Pacers game (depending on the season).

Cincinnati, Ohio (4.5 hours)

Cincinnati sits on the Ohio River, and you’ll have great views from both the Ohio and Kentucky sides. The zoo is one of the best in the country, and your family will enjoy all the activities at the riverfront park. Try the local chili! It’s served over spaghetti and is different than what you’re used to!

St. Louis, Missouri (4.5 hours)

Home to the famous Gateway Arch, you’ll find many free attractions, including the zoo and science center. Check out the City Museum because it isn’t actually a museum – it’s a massive indoor/outdoor playground built from reclaimed materials. How do they describe themselves? Weirdly Wonderful!

Detroit, Michigan (4.5 hours)

Detroit has come a long way from its dark years. The Henry Ford Museum in nearby Dearborn is worth the trip alone. It’s massive and covers everything from presidential limos to the civil rights movement. The downtown area has a nice riverwalk and Belle Isle Park, a 982 acre island in the Detroit River.

Chill Towns & Cultural Spots

Madison, Wisconsin (2 hours)

Situated between two lakes, Madison has a beautiful downtown centered around the Capitol building. The university gives the city energy and vibrance. The Saturday farmers market is one of the best in the Midwest, and the food scene is surprisingly excellent for a city of this size.

Bloomington-Normal, Illinois (2-2.5 hours)

Bloomington and its neighboring city Normal have a relaxed vibe with enough to keep you busy for a weekend. The Children’s Discovery Museum is highly rated, and the Constitution Trail offers miles of paved paths for walking or biking with the family.

Champaign-Urbana, Illinois (2.5 hours)

This is home to the University of Illinois and gives off a smart, laid-back feel. You can check out the Japan House for beautiful gardens, the Krannert Art Museum, or just enjoy the numerous delicious eateries that have popped up to serve the university community.

Springfield, Illinois (3 hours)

Springfield is all about Abraham Lincoln. You’ll absolutely want to visit The Presidential Library and Museum – they’re modern and engaging, not old and stuffy. You can also visit Lincoln’s home, his law office, and his tomb. Don’t forget to check out the Old State Capitol where he gave famous speeches.

Grand Rapids, Michigan (2.5 hours)

Once a furniture manufacturing town, Grand Rapids is now known for being a thriving arts scene. The downtown area has a ton of breweries to check out. You’ll also find good restaurants and museums along the river. For the art lovers, make sure to check out The Frederik Meijer Gardens where you’ll see sculptures combined with beautiful plant collections.

Iowa City, Iowa (4 hours)

Little known fact: Iowa City is the only UNESCO City of Literature in North America. Have a teen thinking about going to university here? The university campus is beautiful, and the downtown area has great bookstores. You’ll enjoy the relaxed, intellectual vibe throughout. And you can explore the pedestrian mall area where you’ll find plenty of restaurants and shops.

Spring Green, Wisconsin (4 hours)

This is a great small town to visit because it punches above its weight culturally. It’s home to Frank Lloyd Wright’s Taliesin estate and the American Players Theatre, which performs in a beautiful outdoor setting. Take a drive through the surrounding countryside to experience dramatic hills and valleys unlike the typical Midwest landscape.

Small Towns With Great Vibes

South Bend, Indiana (1.5 hours)

The Notre Dame Campus, with its golden dome and beautiful basilica, is where you’ll want to check out first. Other places of interest are The Studebaker Museum for classic cars, and the South Bend Chocolate Company for tours and chocolate samples! You’ll also find a revitalized downtown area with plenty to explore.

Rockford, Illinois (1.5 hours)

Outside of Japan, Rockford has one of the best Japanese gardens. For a peaceful retreat, make sure to check out Anderson Japanese Gardens. Don’t forget to check out the Discovery Center Museum and Burpee Museum during your stay, and you’ll enjoy the downtown area with restaurants in historic buildings.

Lake Geneva, Wisconsin (1.5 hours)

This has been a popular getaway for Chicagoans since the 1800s. Lake Geneva offers a 21-mile shoreline where you can walk past historic mansions or rent boats on the lake. Summers are lively with beaches and water activities. And the downtown area is known for being small but incredibly charming.

Holland, Michigan (2.5 hours)

Just like the name hints, Holland embraces Dutch heritage with a working windmill and millions of tulips that bloom every May. Make sure to visit the downtown area for nice shops and restaurants,  and Holland State Park offers one of Michigan’s best beaches with the popular Big Red Lighthouse.

Peoria, Illinois (2.5 hours)

Here you’ll find a river town with a nice waterfront area where you can explore museums, restaurants, and plenty of places to walk. The kids will enjoy The Peoria Zoo and the Caterpillar Visitors Center (where you can climb on massive construction equipment). If you’re into nature, check out the Wildlife Prairie Park.

Fort Wayne, Indiana (2.5 hours)

Fort Wayne is a family-friendly place with a Fort Wayne’s Children’s Zoo, an interactive science museum, and botanical conservatory. Three rivers meet in the city center, and your family will enjoy Promenade Park downtown where you rent kayaks to take out on the water.

Saugatuck/Douglas, Michigan (2.5-3 hours)

These artsy beach towns feature Oval Beach which has massive sand dunes you can climb, and beautiful calm waters along Lake Michigan. The small downtowns have restaurants and shops that are a mix of art galleries, artisan gems, and quirky local culture. Try taking the hand-cranked chain ferry across the river just for fun.

Door County, Wisconsin (4 hours)

Door County is a 70-mile peninsula with shores lined with quaint lighthouses and charming small towns. It sorta feels like New England dropped into Wisconsin. Things to do include visiting state parks, watching a traditional fish boil, picking cherries in season, or just enjoying the small-town pace and natural beauty around you.

Traverse City, Michigan (4.5 hours)

This destination sits at the edge of our 4.5 hour radius, but it’s definitely worth the drive. Sleeping Bear Dunes National Lakeshore offers massive sand dunes with stunning views of Lake Michigan. This area is especially known for cherries and wineries, and you’ll want to check out all the great restaurants and shops downtown.

Bayfield & Apostle Islands, Wisconsin (4.5 hours)

For a more rugged getaway, head over to Lake Superior’s south shore. You can kayak through sea caves in the summer (or walk through ice caves in the winter). You can also take the ferry to Madeline Island or a boat tour of the 22 Apostle Islands to see lighthouses and wildlife.

Tips For Your Trip

• Call Ahead: Some smaller towns have limited hotel options that fill up fast, especially during peak season.
• Check The Weather: Pack layers and be flexible with outdoor plans – you know that Midwest weather can change pretty quickly.
• Get Off The Beaten Path: The best experiences come from talking to the locals when you arrive. Ask for recommendations at hotels and local shops.

Yes, we are The Ben Lalez Team and help buyers and sellers in Chicago. But we also know that Chicago’s central location really is the perfect place to plan road trips all across the Midwest.

Thinking about moving to Chicago? Contact our team today and we’ll be happy to give you a friendly Chicago welcome!

The post The Best Road Trips From Chicago appeared first on Ben Lalez.