Editor’s note: Summer 2020 was a wild one! We’ve transitioned to cold-weather activities in Chicago, but we’ll see you back here next May with suggestions on making the best of summer 2021 in Chicago! Stay safe and stay home as much as possible this winter, Chicago!

Smile. Play. Repeat. Good — you’ve got the basics of a perfect summer. Now add a few highlights to your warm-weather bucket list. It’s prime time to explore all that Chicago and the surrounding area has to offer, from hunting trolls to cheering on dragon boats. Here are our top to-dos this summer with kids.

photo: Morton Arboretum via Maria Chambers

1. Troll take-over at Morton Arboretum. Seek and find the 15- to 20-foot-tall guardians of the forest constructed from reclaimed wood hiding in the woods, meadows and vast open spaces. More details.

2. Play a round of miniature golf. Mini-golf. Putt-putt. Goofy golf. Adventure golf. Shorties. No matter what you call it, you have a blast playing it. Most of Chicago’s mini-golf courses are pure, kitschy fun and are only open for a limited time each year. So grab a short pencil and head to one of our city and suburban favorites. More details.

3. Attend a Pride Fest. Honor Pride Month in person Jun. 27 at the People’s Pier for the 5th consecutive year of Navy Pier Pride. Celebrate equality, love and the LGBTQ+ community with a free daylong celebration that includes live musical performances. More details

4. Hike a trail even toddlers will love. You could hang out in the urban jungle all summer and never run out of family fun. But how about adding fresh air, unforgettable scenery and a chance to spy on animals in their natural habitat? More details.

5. Beat the heat at your local splash pad. Lazy days at the pool are a summer must. Even better? Raging days at splash pads. You’ll have to wait until later in the summer to play due to Covid-19 restrictions, but we’ve uncovered spots that are neighborhood gems while others are all-out amusement park-style destinations. Either way, you and your tot will be happy to cool off without taking a dunk or forking over much moola. More details.

6. Staycation in one of the best cities in the world. Summer is not the time to be heading out of town, as it’s the best time to be a Chicagoan—even with Covid-19 restrictions in place. But sometimes a break from your own four walls is needed and we found hotels with great kid-centric amenities. More details.

15th Dragon Boat Race for Literacyphoto: Chinatown Dragon Boat Race

7. Watch the Dragon Boat Race for Literacy. Watch a traditional Chinese Dragon Boat Race (for free) as 30 boats head down the Chicago River from Ping Tom Memorial Park. The roots of this ancient competition date back more than 2,000 years. This year’s date hasn’t been postponed until August 22, but the event typically includes live music and dance performances, kid’s activities, vendors and special guests. More details.

8. Pick (and eat!) loads of berries. Make your summer a whole lot sweeter by making the rounds at local u-pick berry farms. More details.

9. Participate in a virtual donut race. You read that right. Not only do you receive a donut at the finish line, but this virtual race can be completed any time in the month of August. More details. 

10. Bike the 606. Chicago’s 606 biking trail stands on a former elevated train line. Connecting six neighborhood parks at ground level with numerous art installations along the route, the 606 gives kids a sweet (rooftop) view of the city. More details.

11. Dabble in different activities with Pearachute. Encourage your little multi-taskers to try a range of activities and summer camps (lots of virtual options!) at some of the top kids’ classes in Chicago with Pearachute, the one-stop solution for fun. More details.

12. Meander through the North Shore Sculpture Park. Walk. Bike. Run. Skip. Gallop. However you make your way down this two-mile trail, you’re sure to enjoy the sights. The paved path is lined with sculptures from artists across the world. More details.

13. Shop the Wicker Park Farmers Market. The wildly popular Wicker Park Farmers Market is back, every Sunday, beginning Jul. 5. More details.

14. Compete in the Chicago Ducky Derby. Watch as more than 50,000 yellow rubber duckies splash their way into the Chicago River on August 6 from the Columbus Drive bridge, raising money for Special Olympics Illinois. Put a duck in the game by adopting your own for only $5. More details.

15. Hail a water taxi. Shoreline Water Taxis are a cheap, convenient and fun mode of city transport. Travel via the Chicago River to Chinatown, Navy Pier the Museum Campus, Willis Tower, Michigan Avenue and Union Station while feeling the wind whipping through your hair. More details.

16. Romp on a Chinatown playground. Ping Tom Memorial Park is a 12-acre park located in Chinatown, along the Chicago River, making for a stunning green space with outstanding river views. The Asian-inspired landscaping and structures make for a more interesting park experience and the playground contains elements to keep all kids amused. More details.

17. Cruise the waterways on a Fireboat. Once the largest diesel-powered Fireboat in the world, the Fred A. Busse is now set to share a bit of history with its passengers. More details

18. Rope fake cattle at Onesti’s Wild West Town. Your little buckaroo would love to meet a real cowboy (why else would he spend playtime chasing bad guys and roping imaginary cattle?). Skip the flight to Wyoming and do the next best thing: spend a day at Onesti’s Wild West Town. More details.

19. Watch a movie under the stars. The mother of all outdoor film events is put on by Chicago Park District and typically spreads across your favorite green spaces. This year is a bit more limited with just one scheduled so far: Aug. 21 at Pottawattomie Park. Best part? It’s free! More details.

20. Make a splash at Raging Waves. Splish, Splash! Illinois’ largest waterpark dedicated to family fun for all ages, Raging Waves, is planning to kick off their season late June or soon thereafter. They invite locals and travelers alike to soak up the best moments of summer. More details.

21. Go on a lightening-fast cruise. It’s fast and furious aboard the 75-minute Seadog, which jets off from Navy Pier, speeds along the lakefront, then zips down the Chicago River. The fast-paced excitement makes it the most kid-friendly architectural cruise of all. More details.

22. Take a spin on Navy Pier’s Ferris Wheel. Get a birds-eye view of Chicago on Navy Pier Ferris Wheel! Among the top six tallest Ferris wheels in the United States, this ride features closed, air-conditioned gondolas that are perfect for taking a quick break from summer’s swelter. More details.

23. Tour the Baha’i Temple gardens. Take in the beauty of Baha’i Temple with a walk around their gardens. Once restrictions are lifted, you can get lost in the charms of this house of worship for followers of the Baha’i faith (it’s open to the public for free, self-guided tours). More details.

24. Build sandcastles at Ohio Street Beach. Located near Navy Pier, this right-sized kid-friendly beach provides the perfect atmosphere for a family outing. More details.

25. Hit up a hot dog stand. Love ’em or leave ’em, hot dogs are big in Chicago, and if your kids haven’t begged for one yet, they will soon—and they get a pass on the sacrilege of using ketchup. Grab one at a legendary local spot and turn eating into an adventure. More details.

Get creative with hot dogs at home by reading our story 25 Totally Unique Hot Dog Recipes.

26. Discover the magic of the Original Rainbow Cone. The colors of the rainbow never tasted so good with five flavors in one scoop (chocolate, strawberry, Palmer House vanilla with cherries and walnuts, pistachio and orange sherbet). If you celebrate a summer birthday, check out the Rainbow ice cream cake. More details.

27. Try the New Slide at Raging Waves. Raging Waves is treating Chicagoans to a brand new experience at their already tricked out waterpark. Aussie Mat Dash is a six-lane mat racing waterslide on which six riders race side-by-side in tunnels to the bottom. More details.

photo: Jo Jo’s Milk Bar

28. Grab an over-the-top treat from Jo Jo’s Milk Bar. JoJo’s Milk Bar brings River North a nostalgic take on creative desserts and a reimagined and elevated take on classic diner fare. Along with deliciously whimsical desserts, you’ll find tongue-in-cheek decor including a lifesize Lite Brite wall, Got Milk mural and more. More details.

29. See Brookfield Zoo’s temporary Dinos Everywhere. Once Brookfield Zoo swings open their gates to the general public Jul. 8, you’ll be greeted by 40 animatronic dinosaurs that are BIGGER and BADDER than any dinos you’ve ever met. More details.

30. Attend the Water Lantern Festival. This magical night includes the beauty of thousands of lanterns adorned with your letters of love, hope and dreams reflected upon the water, Jul. 25 in Lincoln Park. More details.

31. Search Chicago for the best Chocolate Chip Cookie. Chicago does the indulgence justice because we have kid-friendly bakeries and restaurants that make delicious, from-scratch versions of the treats—from cookies as big as your head to infused deliciousness. You’re never far from your next fix. More details.

32. Have a sleepover with Mother Nature. Take your family on a glamping trip where social distancing is a breeze. Lock arms with Mother Nature while you camp in style with special touches like cozy beds, stocked kitchens and even air conditioning. More details

Gather ideas that’ll impress the kids in our story 15 Ways to Up Your Backyard Camping Game.

photo: Big Monster Toys via Maria Chambers

33. Make a few wacky roadside stops. Many of the historic and wacky places in Chicago can be easily and safely seen from the comfort of your car to accommodate social distancing, and your kids just might think you’re slowly turning into Mrs. Frizzle from The Magic School Bus. More details

34. Whip up some homemade icre cream. I scream, you scream, we all scream for ice cream. Thankfully, it’s easy to make ice cream at home (without a machine, even!). We pulled together six machine-free, fool-proof methods—including how to make ice cream in a bag—to try at home this summer. More details

If you’d rather leave the ice cream making to the professionals, check out our story Old-School Ice Cream Parlors That Are Sweet City Secrets.

35. Play at a Kohl Children’s Museum Pop-Up. The Kohl Children’s Pop-Up Museum will make its return to Round Lake Beach, every Tues.-Sat., Jun. 23-Jul. 24, with old favorites and two new exhibits for one-hour sessions of family play. More details.


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36. Pay a Visit to Shedd Aquarium. Shedd is opening Jul. 3 for in-person visits with safety measures in place, including mandatory mask-wearing. If you want to make Shedd a part of your summer, but you’re not quite ready for an in-person visit, sign the kids up for their virtual summer camp Summer Splash: Stay Home Edition for stay-at-home fun. More details

— Maria Chambers


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