Hey there, Chicago lovers!

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!