Hey there, future Chicago visitor!
So you’re thinking about spending a summer weekend in our city? Good call! Chicago in the summer is the kind of place that gets under your skin in the best way possible, and we know you’ll leave here already planning your next trip back.
We’re the Ben Lalez Team, and after helping over a thousand families make Chicago their home over the past decade, we’ve gotten pretty good at showing people what makes this city special. Summer here really is something else. The lakefront comes alive, every neighborhood has something going on, and there’s this energy that just makes you want to be outside exploring.
If it’s your first time here and you’ve only got a couple of days, here’s how to make them count. We’re going to show you the Chicago that locals love while hitting those spots that make for great stories back home.
Before You Arrive: What You Need to Know
When To Visit
June through September is the best time to enjoy Chicago. The weather’s great, festivals are happening everywhere, and you’ll catch the city at its most vibrant. Summer brings all kinds of surprise events that add to the fun. You might stumble onto the Chicago Duck Derby in August, where thousands of rubber ducks race down the Chicago River. Or you could be here during Navy Week with ship tours and air shows. That’s the thing about summer in Chicago – there’s always something unexpected happening.
Getting Into The City
You’ll probably fly into O’Hare or Midway. From O’Hare, take the Blue Line for about 45 minutes straight into downtown. It’s cheap, easy, and gives you a good preview of different neighborhoods on the way in. From Midway, the Orange Line gets you downtown in about 30 minutes. Both connect right to our transit system, so you’re in the thick of things pretty quickly.
Getting Around
Chicago is super walkable, but our public transit system is your best friend here. Grab a CTA Ventra card or just tap your phone or credit card on the L trains and buses. The system is pretty straightforward once you get the hang of it. For those perfect summer days, Divvy bike stations are everywhere. Cycling along the lakefront is honestly one of the best ways to see the city. Our grid system makes navigation simple too, even if you’re new here.
Where To Stay
River North puts you right in the middle of our best restaurant and nightlife scene. It’s buzzing with energy and perfectly located for exploring. The Loop keeps you close to major landmarks and cultural stuff. If you want that young, creative traveler vibe, check out places like the Freehand hostel or one of our boutique hotels. They really capture Chicago’s independent spirit and usually put you in interesting neighborhoods.
Day 1: The Heart Of Chicago
Morning
Start your day at Goddess and the Baker. They’ve got great vibes and food that works for pretty much any dietary thing you’ve got going on. Their coffee hits different when you’re excited about exploring a new city.
Walk over to Millennium Park early to beat the crowds. Cloud Gate (aka “The Bean”) is way more impressive in person than in photos. You’ll want those perfect shots without fighting through tour groups. Don’t skip Crown Fountain either – kids splash around while digital faces “spit” water. It’s pretty cool. The Lurie Garden is this peaceful spot that showcases native prairie plants. It’s a nice contrast to all the urban energy around you.
Take a stroll down Michigan Avenue to soak up the Magnificent Mile atmosphere. If it’s not Tuesday or Wednesday, think about popping into the Art Institute. Their collection is world-class. You can see Grant Wood’s “American Gothic” and this massive Georges Seurat painting that inspired the musical Sunday in the Park with George.
Afternoon
Head to the Chicago Riverwalk for a snack or drink. The riverwalk transformed what used to be industrial waterway into one of our most beautiful spaces. You can grab everything from craft cocktails to ice cream while watching kayakers paddle by and checking out the amazing architecture all around you.
Book an architecture boat tour for early evening. This isn’t just tourist stuff – it’s actually really cool. Chicago basically invented the skyscraper, and seeing our architectural history from the water during golden hour makes for some of the best photos you’ll ever take. You’ll learn about legends like Louis Sullivan and Frank Lloyd Wright while floating past buildings that changed the world.
Evening
Time for deep dish pizza at Lou Malnati’s. Yes, it’s touristy, but it’s also a Chicago thing. The butter crust, chunky tomato sauce, and cheese blend create something completely different from what most people call pizza. Come hungry and be patient – good deep dish takes time.
End your night catching the skyline from Milton Lee Olive Park or Cindy’s Rooftop. The park gives you that classic Chicago skyline shot, while Cindy’s has craft cocktails and panoramic views. If you want the full tourist experience, Navy Pier’s Ferris wheel looks pretty cool lit up at night. Or you can see The Bean all lit up after dark when the crowds have cleared out.
Day 2: Neighborhoods, Food, And Lake Life
Morning
Fuel up with breakfast at Beatrix, Wildberry, or Lou Mitchell’s. Beatrix has healthy options in a bright, modern space. Wildberry is famous for their pancakes and fresh ingredients. Lou Mitchell’s is this classic Chicago diner that’s been serving hearty breakfasts since 1923. Each one gives you a different slice of Chicago’s food culture.
Rent a Divvy bike and ride down the Lakefront Trail. This 18-mile path along Lake Michigan is one of Chicago’s best features. The trail connects beaches, parks, and neighborhoods while giving you incredible lake views. You’ll get why we’re so proud of our lakefront access. Stop by North Avenue Beach if you want to dip your toes in Lake Michigan or just people-watch from the sand.
Afternoon
For lunch, head to Mr. Beef for an authentic Italian beef sandwich. This is especially cool if you’re a fan of “The Bear” – the show put this local spot back on the map, but it’s been serving Chicago-style beef sandwiches for decades. If you want the full Chicago experience, try Portillo’s for their famous hot dogs paired with a chocolate cake shake. It sounds weird, but trust us on this one.
Explore Lincoln Park neighborhood and the actual park it’s named after. The Lincoln Park Zoo is free and surprisingly great, with everything from big cats to farm animals. The Nature Boardwalk offers a peaceful walk around a pond filled with local wildlife. Even if you just find a bench and watch people enjoying the green space, you’ll get a sense of how Chicagoans live during our beautiful summer months.
Walk through Old Town along Wells Street for charm, boutique shopping, and cozy cafes. This neighborhood keeps its historic character while offering modern amenities. The tree-lined streets and well-preserved architecture make it feel like a small town within the big city.
Evening
Try thin crust pizza at places like Zazas if you want a change from deep dish. Chicago-style thin crust is totally different from deep dish but equally important to our pizza culture. The crust is crispy, almost cracker-like, and cut into squares instead of triangles.
If the Cubs are in town, catch a game at Wrigley Field. Even if you’re not a baseball fan, Wrigley’s atmosphere is pretty infectious, especially during summer evening games. Or catch a show at Second City, where tons of Saturday Night Live cast members got their start. Chicago’s comedy scene is legendary, and seeing improv and sketch comedy at its birthplace is a unique experience.
Bonus Ideas For Longer Stays
If you have extra time, think about 360 Chicago or the Skydeck at Willis Tower for incredible city views. Both offer amazing perspectives, but they’re different experiences. The Skydeck has those famous glass ledges that extend from the 103rd floor, while 360 Chicago offers “Tilt,” where you lean out over the city in a glass enclosure.
The Museum Campus houses the Shedd Aquarium, Field Museum (home to Sue the T-Rex), and Adler Planetarium. Each one deserves half a day if you’re into museums. The campus itself offers beautiful lake views and connects easily by public transit.
For a taste of Chicago’s neighborhood diversity, explore Andersonville or Logan Square. These areas give you the authentic local experience without tourist crowds. Andersonville celebrates its Swedish heritage while embracing LGBTQ+ culture. Logan Square buzzes with art galleries, craft breweries, and some of the city’s best restaurants.
Food: The Real Chicago Experience
Let’s talk about what you should actually eat and why it matters:
Deep Dish Pizza (Lou Malnati’s, Pequod’s) – This isn’t just pizza. It’s Chicago’s contribution to American food culture. The thick crust, layers of cheese, and chunky tomato sauce create something totally unique. Lou’s is the most accessible option, while Pequod’s has this caramelized crust that locals love.
Italian Beef (Mr. Beef) – Especially meaningful for “The Bear” fans, but this sandwich represents Chicago’s working-class Italian-American heritage. Thin-sliced beef in spicy jus, served wet with hot peppers on a French roll. It’s messy, delicious, and completely Chicago.
Chicago-Style Hot Dogs (Portillo’s) – An all-beef frank with yellow mustard, chopped onions, bright green relish, tomato wedges, pickle spear, sport peppers, and celery salt on a poppy seed bun. Never, ever ask for ketchup. The chocolate cake shake is this local obsession that’s worth trying.
Thin Crust Pizza (Zazas) – Often gets overshadowed by deep dish, but equally important to Chicago pizza culture. The ultra-thin, cracker-like crust cut into squares represents our tavern-style pizza tradition.
Classic Diner Food (Lou Mitchell’s) – This breakfast spot has been serving Chicago since 1923. Double-yolk eggs, thick-cut bacon, and hash browns represent the hearty, no-nonsense approach to dining that defines a lot of Chicago’s food culture.
Coffee Culture – From the fancy Starbucks Reserve Roastery to neighborhood spots like Mojo Coffee, Chicago takes coffee seriously. Summer means iced drinks on patios and coffee shops that spill onto sidewalks.
Quick Itinerary Snapshot
Day 1: Millennium Park and The Bean → Michigan Avenue → Riverwalk → Architecture boat tour → Deep dish dinner → Skyline views
Day 2: Neighborhood breakfast → Lakefront bike ride → Lincoln Park exploration → Italian beef or hot dogs → Cubs game or Second City comedy
Final Thoughts
Here’s what we want you to know about Chicago. This city isn’t just a bunch of tourist attractions you check off a list. It’s a feeling. It’s the way the lake breeze cools you down on a hot afternoon. It’s discovering a Chicago street festival you didn’t know existed. It’s that friendly argument you’ll have with locals about which pizza place is actually the best. It’s realizing that a city this big can still feel welcoming and approachable.
Whether you’re here for a weekend or thinking about a longer stay, Chicago has this way of making people feel at home. And who knows? Maybe after experiencing a summer weekend here, you’ll start thinking about what it would be like to call Chicago home year-round.
If you find yourself wanting to explore that idea, give us a shout. We’d love to grab coffee and share more insights about what makes this city so special. After all, the best Chicago experiences often start with good conversation and great recommendations from people who truly know and love this place.
Welcome to Chicago. We think you’re going to love it here!
