25 Things to Do in Chicago Before School Starts

Two little Chicagoans, fresh from the splash pad at 31st Street Harbor, contemplate going to the beach.
Two little Chicagoans, fresh from the splash pad at 31st Street Harbor, contemplate going to the beach.
7/20/25 - By Bonnie Broeren

If seeing school supply lists is sending you and your kids into a panic over the impending end of summer, stay calm, and summer on! We've done the research, and rounded up the ultimate Chicago summer bucket List, complete with all the outdoor movies, festivals, and FREE summer activities for families in Chicago that you'll want to fit in before school starts up again.

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1. Green City Market in Lincoln Park, Avondale, and West Loop

 Chicago hosts amazing farmers' markets, where the whole family can snack, shop, and enjoy cooking demonstrations and live entertainment. Check out their calendar for hours and exact locations.

2. Find a summer street festival

This is one of our favorite parts of summer, and there are dozens still left to go on our big master list! We love Taste of Lincoln Avenue and Chalk Howard Street. 

3. Go on a boat ride

If you haven't experienced Chicago by boat yet, prepare to fall in love with this city all over again during one of the Best Boat Rides in Chicago. Head to Navy Pier and check out one of the family-friendly cruises, or take the water taxi to the museum campus. 

4. Navy Pier Fireworks

Navy Pier hosts a FREE spectacular fireworks display every Wednesday and Saturday evening through the end of August. You can see the fireworks from the pier or any nearby establishments, parks, or beaches. Or, cross off two items on your Chicago summer bucket list in one fell swoop by watching the fireworks from a boat on a fireworks cruise!  

RELATED: 100 Things to Do With Chicago Kids Before They Grow Up

riding the rides at Navy pier should be on everyone's Chicago summer bucket list
Head to Navy Pier to soar on the Centennial Wheel, then hit the other thrilling rides. Photo courtesy of Navy Pier

5. Centennial Wheel

Have you ridden the Centennial Wheel? Or the other rides on the pier? Check these out and more of our Things To Do on Navy Pier

6. Visit a Free Beach 

Chicago has a ton of beaches along the Lake Michigan shoreline. A personal favorite is 31st Street Beach, with its snacks, new playground, splash pad, and beautiful harbor. 

7. Take a dip in a free Chicago Park District Pool

The Chicago Park District maintains fifty FREE outdoor pools. most of which are accessible. Many also have water playgrounds, and a few even have twisty-turny water slides! Holstein Pool is one of our favorites, located in Bucktown with fun free attractions to visit before or after your swim including the 606 Trail. Check out our other favorites here

8. Visit a Splash Pad

If you can't commit to a swim, but still want to cool off, check out some of Chicago's Best Splash Pads and Water Playgrounds

​Grant Park Music Festival photo courtesy of the Chicago Park District 
Having fun dancing at Grant Park Music Festival. Photo courtesy of the Chicago Park District

9. Grant Park Music Festival

Check out the Grant Park Music Festival for world-class concerts at the Jay Pritzker Pavilion. Or, for a more intimate (and free) experience, see a Night Out in the Park concert at one of Chicago's many neighborhood parks.

10. The Field Museum 

Experience the wonder of the Field Museum of Natural History. If you have a dinosaur lover in your family, visiting this museum to hang with Sue is a must when checking off the things on your Chicago summer bucket list. The museum is free for Illinois residents on Wednesdays during the summer! Read our review first to make the most of your visit. 

RELATED: 100 Free Things to Do With Chicago Kids This Summer

11. The Shedd Aquarium 

Did you know that the Shedd Aquarium has an actual baby Beluga whale? It also has an outdoor stingray petting station during the summer and several live shows throughout the day. The kids will especially love the animal, where they can learn about sea lions, dolphins, and that adorable Beluga! Plus, the aquarium is free on Tuesday evenings throughout the summer. Read our review before you go. 

12. Broadway in Chicago

From Beauty and the Beast to Twenty-Sided Tavern, there are a few kid- or tween-friendly Broadway in Chicago performances to treat yourself and your kiddo to before school starts. 

13. Adler Planetarium

Stay up past your bedtime and gaze at the moon. Get a glimpse of the moon through the Adler Planetarium's powerful telescope at Doane at Dusk for FREE, something that should be on everyone's Chicago summer bucket list. Read more about Adler here

14. Morton Arboretum

Stroll through miles of beautiful trees and gardens. Families can hike through the Morton Aboretum, where kids will love the Children's Garden, and right now, you can enjoy the Wonder Woods, a new tree-themed mini golf course, or Vivid Creatures, five giant colorful statues of Illinois wildlife.

15. Art on the Mart

See art and architecture at nightNeed more excuses to stay up past your bedtime? Go see Art on the Martafter dark, a massive public art installation, featuring images from Chicago artists projected onto the 2.5-acre river facade of the Merchandise Mart. 

16. Play in Millennium Park

There's plenty to do at this iconic Chicago park. Home to one of the city's Best Splash Pads and Destination Playgrounds, Millennium and Maggie Daley parks are must-see summer destinations. Play tourist as you splash in Crown Fountain, take a selfie with Cloud Gate (affectionately known as "The Bean"), or climb a wall (or a whale) at Maggie Daley Park.  

Chicago Cubs fans at Wrigley Field checking of things on their Chicago summer bucket list 
Chicago Cubs fans at Wrigley Field. Photo by Ryan Dickey via Flickr CC BY-NC-ND 2.0

17. Cubs or White Sox Game 

Now, the tough question: Cubs or Sox? Why not both? The Chicago White Sox hosts Family Sundays, and the Cubs host Kids Sundays, each featuring family-friendly themes, activities, and ticket packages. 

18. See the Bud Billiken Parade

This is the true sign that summer is over in Chicago. This 94-year-old event takes over the South Side on the second weekend of August every year, encouraging kids to stay in school.

19. Movie in the Park

Watch a movie under the stars. There's something about watching movies outside that feels quintessentially summer. The Chicago Park District hosts free movies throughout Chicago, and our calendar is chock full of even more.

20. Watch the Chicago Air and Water Show

One of the coolest free things you'll see every summer is the planes flying in formation over the lake the third weekend in August. Find a spot on the beach or a friend with a boat to enjoy the show from up close!

21. Lincoln Park Zoo 

Lincoln Park has a FREE zoo and farm in the zoo, both with calendars full of exciting, family-friendly fun.  

22. Brookfield Zoo

The Brookfield Zoo is the largest in Chicagoland. It's newly opened Bramsen Tropical Forests exhibit gives visitors a fantastic up-clsoe view of fascinating primates.

23. Griffin Museum of Science and Industry

For your science lovers, there are endless things to see and explore at the Griffin Museum of Science and Industry. Superhero fans will love the new Spiderman exhibit, while seafaring little folk will want to learn about the German submarine from World War II, and everyone will love the coal mine and train exhibits. Read our review here

24. Go on one last quick road trip

We recommend Indianapolis, which we did over spring break! We're also trekking up to Madison before school starts. 

25. Visit a Michelin Star restaurant

The best time to dine at one of these fancy places is during the off-peak hours — which is perfect when there's no school!

 

 

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