Unique Things to Do in Chicago
Chicago's most unique experiences include The Hideout, a tiny bar in an industrial alley hosting eclectic live shows, Empty Bottle's indie music scene, Green Mill's speakeasy jazz since 1907, and UP Comedy Club above Second City.
5 places · 1 free · Updated Oct 2026
1,700-acre outdoor museum of trees and plants with a dedicated Children's Garden featuring climbing structures, a splash pad, a hedge maze, and nature play areas. The Troll Hunt (giant wooden troll sculptures hidden in the woods) is a year-round scavenger hunt kids obsess over. 25 miles west of downtown. Worth the drive.
A city park with a small free zoo featuring ducks, alpacas, goats, and other animals. Also has a playground, splash pad, tennis courts, and a fieldhouse with free Park District programs. The zoo is compact enough for toddlers and the playground is well-maintained. A hidden gem on the far North Side.
Art Deco jazz club, former Prohibition speakeasy -- Al Capone's favorite hangout. Live jazz seven nights a week, small cover. Sunday night Uptown Poetry Slam has run since 1986 -- longest-running in the country. Cash only. They will shush you.
Chicago's underground music cornerstone since 1992. 400 capacity, dive bar vibe, no pretension. Experimental noise, indie rock, electronic -- whatever's interesting. Free Monday shows. The kind of room where you hear a band two years before everyone else does.
Century-old bar tucked in an industrial pocket of Bucktown. Prohibition-era hangout turned into one of Chicago's most intimate live music rooms. Alt-country, folk, rock, comedy, literary events. About 100 capacity -- shows sell out fast.