There’s truly nothing like summer in Chicago.
Block parties spill into the streets, the lakefront becomes everyone’s favorite hangout, and you can hear the beat of a street festival happening in Chicago before you even know what it’s for.
I’ve planned entire trips around Chicago summers. That’s just how good they are. Even after living here, I still get that same excitement every season when the city flips the switch.
Whether you’re cooling off with frozen treats, watching fireworks at Navy Pier, kayaking along the Chicago River, or exploring a new neighborhood festival, this is the essential guide for your first or forever summer in the city of Chicago.
Here are 43 of the best things to do in Chicago this summer. Whether you’re crossing off your Chicago bucket list, revisiting your favorite iconic landmarks, or seeking out something new, this is your ultimate seasonal guide.
Locals, tourists, planners, and wanderers: this one’s for you.
How to Spend Summer Outdoors in Chicago
1. Hit the waves of Lake Michigan on a pontoon, sailboat, yacht, or kayak.
2. Root for the Cubs or White Sox all summer long.
3. Rock climb for free on the South Side at Steelworkers Park.
4. Unwind in a secluded park or garden.
5. Soak up the sun at hidden gems like Promontory Point.
6. Go mural scouting in one of Chicago’s coolest neighborhoods.
7. Cruise Lake Michigan on a pontoon, yacht, kayak, or sailboat.
8. Take a water taxi to Chinatown or Goose Island.
9. Catch a breeze on a walk or bike ride along the Lakefront Trail.
10. Swim or sunbathe at one of Chicago’s 24 publicbeaches.
11. Experience free movies, music, and workouts in the park (Millennium Park or Chicago Park District).
12. Hike local trails or day trip to a nearby state park.
13. Visit a Chicago public pool or splash pad for a no-cost cool-down.
14. Picnic at Promontory Point or in Jackson Park.
15. Explore the city with a Divvy bike or scooter rental.
16. Take a scenic stroll along the Chicago Riverwalk.
Chicago Summer Events, Festivals, and Cultural Activities
17. See a play or musical at a theater downtown.
18. Hop aboard an architecture cruise or a themed walking tour.
19. Join a community 5K or 10K run for a good cause.
20. Plan an interactive indoor date night The Escape Games Chicago.
21. Learn something new at Chicago’s Museum Campus. The Art Institute and Museum of Science and Industry are must-sees as well.
22. Sing with your favorite music artist at a summer music festival.
23. Treat yourself to a luxe spa experience.
24. Explore one of Chicago’s most unique museums.
25. Tour Chicago’s most popular attractions with aGoPass.
26. Watch free fireworks at Navy Pier on Wednesdays & Saturdays.
27. Catch a neighborhood block party or porch concert.
Where to Eat and Drink in Chicago This Summer
28. Start your weekend with a bottomless and boozy brunch.
29. Savor an icy treat from a novelty dessert shop.
30. Quench your thirst with beer from a local brewery.
31. Sample the best Southern and soul food restaurants from Black-owned restaurants.
32. Tour and dine Chinatown’s food scene.
33. Grab an iconic Chicago-style deep-dish pizza. Or tavern, if that’s your style.
34. Sip cocktails with a view at the best rooftop bars in Chicago.
35. Chill out at a neighborhood patio restaurant.
36. Sample bits from aChicago food festival.
Haute Tip: Chicago is a city worth exploring year-round. Start planning now with our guide to the top fall experiences in Chicago.
Chicago Summer Markets, Makers, and More
37. Shop local at a summer artisan’s market.
38. Grab fresh produce from a Chicago farmers’ market.
39. Browse local bookstores and build your summer reading list.
40. Refresh your wardrobe with finds from local fashion boutiques.
41. Add to your vinyl collection from a local record shop.
42. Explore the art scene with free gallery shows and street art tours.
43. Take a DIY class at a local shop or maker space.
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