Top 100 Things to Do in Chicago in 2026 (Locals Guide)
The ultimate Chicago bucket list from a local. Hidden gems, iconic landmarks, best food, nightlife, and free activities in the Windy City.
The Complete List
#1. Millennium Park & Cloud Gate
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#2. Art Institute of Chicago
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#3. Navy Pier
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#4. Skydeck Chicago (Willis Tower)
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#5. Architecture River Cruise
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#6. Field Museum
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#7. Shedd Aquarium
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#8. Museum of Science and Industry
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#9. Lincoln Park Zoo (free!)
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#10. Wrigley Field Cubs game
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#11. Deep dish at Lou Malnatis
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#12. Italian beef at Als
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#13. Chicago-style hot dog at Portillos
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#14. Second City comedy show
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#15. Green Mill jazz club
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#16. Kingston Mines blues
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#17. Magnificent Mile shopping
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#18. Oak Street Beach
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#19. Riverwalk walk
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#20. Chinatown dim sum
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#21. Pilsen murals walk
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#22. 606 Trail bike ride
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#23. Garfield Park Conservatory (free)
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#24. Harold Washington Library
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#25. Andersonville shops
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#26. Logan Square food scene
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#27. Wicker Park nightlife
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#28. Humboldt Park
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#29. Promontory Point sunset
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
#30. Chicago History Museum
One of the top picks in coaching/chicago for 2026. Recommended by experts and users alike.
More Coming Soon
This list is actively updated as we discover more great options in coaching/chicago. Bookmark this page and check back for the full 100.
How We Ranked This List
Our rankings are based on user reviews, expert opinions, value for money, and overall quality. We update this list regularly to keep it current for 2026.
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