Entertainment & Experiences in Chicago, IL
25 places · 2 free · 21 indoor · Updated 2026-10-18
Old Town
Tina Fey, Steve Carell, and dozens more started here. $10 shows available nightly.
Two doors from Second City. Touring headliners. Two-drink minimum. Thu-Sun.
In the Second City building. Stand-up format. $15-40. Zanies is next door.
Uptown
Al Capone's hangout. Jazz 7 nights. Cash only. No talking during sets.
50 years of original African American musicals — 2026 season includes Muddy Waters
Loop
American Gothic, Nighthawks, Seurat's Sunday -- all here. Kids under 14 free. Chicago teens under 18 free.
The marquee sign. The grand staircase. $32 tour takes you backstage.
Free concerts all summer. Frank Gehry bandshell. Bring a blanket and a picnic.
Chicago's oldest theater. $15 tix-at-six rush. Collaborations with David Byrne.
The building tour that launched a thousand architecture buffs. Boat tours from $47.
Lincoln Park
Two stages, simultaneous blues bands, until 5am Saturdays. Open since 1968.
Founded by Gary Sinise and John Malkovich. New in-the-round theater. Rush tickets available.
500 capacity. Sister venue to Schubas. Best mid-size room on the North Side.
Near North Side
Improvised Shakespeare Company performs here. Cheaper and weirder than Second City.
World's largest magic venue. Inside the historic McCormick Mansion. Opened 2026.
Live jazz since 1951. Two sets nightly. $10-15 cover. Downtown location.
Free on Tuesdays for IL residents. Rooftop sculpture garden. Wednesday late nights.
Lakeview
311 seats, full bar, $16 tickets. Touring headliners most nights.
165 capacity. The room where everyone plays before they blow up. $10-20.
Ukrainian Village
Free Monday shows. Dive bar vibe. The underground music scene runs through here since 1992.
Bucktown
100 capacity. Prohibition-era bar. Shows sell out fast. Regulars are fiercely loyal.
South Loop
Buddy Guy's own club. Live blues nightly. The man himself plays every January.
Free skate park in Grant Park. Concrete ramps, rails, quarter pipes. All skill levels.
Wrigleyville
Smashing Pumpkins played their first big shows here. 1,100 capacity. Still going since 1982.
Pilsen
1892 opera house turned concert hall. Ornate interior. Czech and Mexican neighborhood heritage.