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91 TO DO
Today's draw — Monday, Aug 3

What should we do in Chicago?

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MON · AUG 3 · CHICAGO
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Andersonville Farmers Market

A compact after-work farmers market in one of Chicago's most walkable LGBTQ-friendly and Swedish-heritage neighborhoods, easy to combine with the strip's vintage shops and restaurants.

Local Life & MarketsFree№ 3029
◎ Andersonville ☾ Wednesdays 3pm-7pm, mid-May through October ✓ Verified Jul 2026
No lists. No scrolling. Just go.

91 hand-picked things to do in Chicago, United States — 35 completely free — each with a real address, price, hours, and an insider tip. Updated July 2026.

Chicago FAQ

What are the best free things to do in Chicago?

Millennium Park & Cloud Gate ("The Bean"), The 606 Trail (Bloomingdale Trail), Lincoln Park Zoo are among the 35 completely free activities in our Chicago list. Each entry includes the address, hours, and an insider tip.

How much do things to do in Chicago cost?

Our 91 hand-picked Chicago activities range from free up to about $57 per person, with most under $25. Use the Free / Budget toggle on the deck to deal within your price range.

How does DrawTheDay pick activities in Chicago?

Every activity is a real, verified place or experience with a current price, address, and opening hours — hand-picked for travelers and locals. Last updated July 2026.