Theatre & shows
Theatre & shows in Chicago
Theatre, opera, magic, cabaret — a curtain time.
Top 12 venues
01
The Drifter
River North · $$$
Speakeasy underneath Green Door Tavern pouring craft cocktails & offering live entertainment.
02
Jazz Showcase
Chicago Loop · $$
Live jazz nightly in a 170-seat room since 1947 — local and national acts, affordable drinks, reserve ahead for good seats.
03
Park West
Lincoln Park · $$$
Midsize 1920s entertainment venue featuring performances by nationally known comedy & music acts.
04
The Tiki Terrace
Des Plaines · $$
Strip-mall tiki bar with hand-carved decor, live hula dancers, and Hawaiian plates — walk in skeptical, leave immersed.
05
The Chicago Theatre
Chicago Loop · $$$
1921 French Baroque palace downtown—3,600 seats, ornate ceiling, multiple bars, bathroom lines get long. Comedy and concerts in a room that feels magical.
06
Civic Opera House
Chicago Loop · $$$
3,500-seat palace for Lyric Opera and Joffrey Ballet — beautiful bones, cramped seats, sightlines that don't betray you even in the nose bleeds.
07
Petrillo Music Shell
Chicago Loop · $
This outdoor music auditorium in Grant Park hosts big-name artists & popular jazz & blues festivals.
08
The Second City
Old Town Triangle · $$
Sketch and improv shows where the hits land and the crowd work saves the awkward bits. Cheap seats, good drinks, the occasional breakout performer.
09
The Den Theatre
West Town · $$
Venue offering live comedy & performances in a 200-seat theater, plus a bar & a lounge.
10
Annoyance Theatre & Bar
Lake View East · $$
Two theaters, improv and sketch to new plays. Bar staff knows their drinks. Late-night shows just as good as prime time — hit it spontaneous.
11
Logan Square Improv
Logan Square · $$
Thursday and Saturday shows with the city's best improvisors — Late 90s, Little Heroes, rotating locals. Community-built, welcoming, hilarious.
12
Drunk Shakespeare Chicago
Chicago Loop · $$$
Shakespeare with a cast that riffs on modern culture, pulls audience members on stage, and hands you shots before curtain. Tight, rowdy, surprisingly sharp.