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.
3 places · Updated Oct 2026
Art Deco jazz club with a storied speakeasy past dating back to Prohibition -- Al Capone's favorite hangout. Live jazz seven nights a week with a small cover charge. The Sunday night Uptown Poetry Slam, running since 1986, is the longest-running poetry slam in the country. Cash only. No talking during performances.
Beloved indie music venue and bar that has been a cornerstone of Chicago's underground music scene since 1992. Capacity of 400 with a no-frills dive bar vibe. Hosts everything from experimental noise to indie rock to electronic music. Many free Monday shows. One of the most respected small venues in the country.
A century-old bar tucked in an industrial pocket of Bucktown that served as a Prohibition-era hangout. Now one of Chicago's most intimate and eclectic live music venues, hosting alt-country, folk, rock, comedy, and literary events. Capacity around 100 -- shows sell out fast. A true Chicago institution with fiercely loyal regulars.