15 Top Things to Do in Chicago This Summer: Your Complete Bucket List

Few things compare to summertime in Chicago. When the cold and snow finally melts away and the days get longer, Chicago transforms into a lively city of rooftop bars, lakefront adventures, and street festivals. As someone who has lived in Chicago for five years, I can confidently say there’s nothing quite like the energy of this city in the summer. 

Whether you’re a local looking to soak up every second or a visitor planning your summer trip, there’s no shortage of ways to make the most of the season. From iconic, bucket-list experiences to hidden gems, this Chicago summer bucket list has all the best things to see, do, and enjoy while the city is at its best.

Your Complete Chicago Summer Bucket List

1. Ride Divvy Bikes Along the Lakefront Trail

Hop on a Divvy bike and cruise along the scenic Lakefront Trail with unbeatable views of the skyline and Lake Michigan. Single rides start at $1 to unlock plus $0.39/minute; day passes are also available.

2. Attend Jazzin’ At The Shedd

Enjoy live jazz, skyline views, and after-hours aquarium access at Shedd Aquarium every Wednesday from May 28 through August 27, 2025, 5–10 p.m. Tickets for Jazzin’ at the Shedd start at $39.95 for adults, with discounts for Chicago residents and members.

3. Eat Your Way Through The Taste of Chicago

Sample dishes from dozens of local restaurants at this iconic (and delicious!) food festival from September 5–7, 2025, with additional neighborhood events on June 28 (Marquette Park), July 19 (Pullman Park), and August 9 (Albany Park). Admission is free; food and drink tickets are available for purchase on-site. Be sure to check out the headliners – one year we saw Nelly perform there for free!

4. Have a Boat Day

Gather your friends and rent a boat or join a charter for a day of sun, music, and floating fun in the Playpen, Chicago’s lively off-shore party zone. Alternatively, book a sunset cruise along the shores of Lake Michigan and take in the stunning views of the city’s skyline during Golden Hour.

5. Watch the Chicago Air and Water Show

Experience thrilling aerial and water performances on August 16–17, 2025, along the lakefront near North Avenue Beach. Admission is free but you will want to arrive early (expect crowds like in the photo below) to secure a good viewing spot along the lake or make a reservation at a waterfront restaurant (Theater on the Lake or Castaways) or rooftop bar (Offshore Rooftop or Cindy’s). 

6. Join a Chicago Architecture Boat Tour

This is one of the most popular activities to do in Chicago and for good reason – it’s both fun and informative! Learn the fascinating history behind Chicago’s skyline while cruising down the Chicago River on this must-do tour. Tours operate daily and tickets typically range from $40–$50.

7. Cheer on Your Favorite Team at a Cubs or White Sox Game

Whether you’re rooting for the Northside or the Southside, nothing says summer like a baseball game in the city. Grab a Chicago-style hotdog and cheer on your favorite team during a summer baseball game at Wrigley Field or Guaranteed Rate Field. 

8. Visit Lincoln Park Zoo & Conservatory

Explore one of the nation’s oldest free zoos and the adjacent conservatory. Admission to both is free, but donations are appreciated.

Looking for more budget-friendly activities in Chicago? Be sure to check out my list of 12 Free Things to Do in Chicago: Budget-Friendly Attractions & Activities!

9. Stroll the Chicago Riverwalk

Grab a drink or bite to eat and enjoy a scenic walk along the vibrant Chicago Riverwalk, featuring restaurants, bars, and public art installations. Stay after the sun sets to experience Art on theMART, a massive nightly projection show displayed on the side of the Merchandise Mart – shows run twice each evening from mid-April through December and are completely free to watch from the Riverwalk.

10. Kayak On The Chicago River

The Chicago River gets a bad rap, but there has actually been tremendous progress made in terms of its conservation and restoration! Paddle your way through downtown for a unique (and surprisingly peaceful) perspective of the city. For a meaningful and educational experience, sign up for one of Shedd Aquarium’s Kayak for Conservation programs, where you’ll learn about local wildlife and help with data collection (no prior kayaking experience is needed)! 

11. Spend the Day at The Beach

Sandy shores might not be the first thing you associate with Chicago, but come summer Chicago’s lakefront turns into a full-on beach destination. Spend the day soaking up the sun, playing beach volleyball, swimming in Lake Michigan, or grabbing a drink at one of the beachside cafés with skyline views. Beach access is completely free, and there are multiple underpasses along Lake Shore Drive that make it easy to get from downtown to the sand without crossing traffic.

12. Watch the Navy Pier Fireworks

Enjoy free fireworks displays at Navy Pier every Wednesday and Saturday night from Memorial Day through Labor Day. Best viewed from the pier, a boat in the playpen, nearby beaches, or from the aquarium’s patio during Jazzin’ at the Shedd.

13. Lounge at a Rooftop Pool

Cool off at one of Chicago’s rooftop pools, such as those at the Robey, Viceroy or Soho House. Access may require a hotel stay, drink minimum or day pass but it’s worth it to go for a swim while enjoying stunning skyline views.

14. Shop at a Local Farmer’s Market

Stock up on fresh produce, baked goods, and flowers at neighborhood favorites like Green City Market in Lincoln Park (Wednesdays and Saturdays, 7 a.m.–1 p.m.) or West Loop (Saturdays, 8 a.m.–1 p.m.).

15. Catch a Free Movie at Millennium Park

Watch free movies during the Millennium Park Summer Film Series at Jay Pritzker Pavilion every Tuesday from July 1 through August 26, 2025. Films start at 6:30 p.m. Arrive early to secure a spot on the lawn and BYOB (bring your own blanket!).

Bonus: Attend a Summer Music Festival

Chicago comes alive with music during the summer, and there’s a festival for every genre. Whether you’re into rock at Lollapalooza (July 31 to August 3), jazz at the Chicago Jazz Festival (August 28 to 31), or exploring local talent at the Windy City Smokeout (July 10 to 13), there’s no shortage of live music to enjoy.

Final Thoughts

Chicago summers are truly something special, with a mix of iconic events, outdoor fun, and a variety of cultural experiences. Whether you’re a local or a first-time visitor, there’s no shortage of ways to enjoy the city’s lively atmosphere during summertime! 

What are you most excited to check off your Chicago summer bucket list?

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