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Music & Comedy, Theatre & Performing Arts
Voila: The Improvised Musical
iO Chicago presents: a fully made-up, off-off-off Broadway style musical every Friday at 10pm in the Fremont Theater. Spend your Friday night with us. See…
Friday January 9, 2026
10:00 p.m. – 11:30 p.m.The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,Music & Comedy, Theatre & Performing Arts
Hitch*Cocktails
A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together…
Friday January 9, 2026
10:00 p.m. – 11:30 p.m.Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.Sports & Recreation
McCormick Tribune Ice Rink
Ice skating at the McCormick Tribune Ice Rink in Millennium Park begins Nov. 21 (weather permitting). Admission to the ice rink will be free, but…
Saturday January 10, 2026
11:00 a.m. – 10:30 p.m.Millennium Park
201 E Randolph StMusic & Comedy, Theatre & Performing Arts
ComedySportz Chicago
Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…
Saturday January 10, 2026
6:00 p.m. – 7:30 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy, Theatre & Performing Arts
The Infinite Wrench
Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…
Saturday January 10, 2026
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…
Saturday January 10, 2026
7:00 p.m. – 10:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphMusic & Comedy, Theatre & Performing Arts
Baby Wants Candy! The Original Completely Improvised Musical
“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…
Saturday January 10, 2026
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St.Music & Comedy, Theatre & Performing Arts
Clued In
After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…
Saturday January 10, 2026
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St., Theater on the Second FloorMusic & Comedy, Theatre & Performing Arts
ComedySportz Chicago
Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…
Saturday January 10, 2026
8:00 p.m. – 9:30 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy, Theatre & Performing Arts
Best Of Annoyance Sketch
Enjoy the best sketch comedy Chicago has to offer! The Annoyance Theatre has been at the crux of the comedy scene in Chicago for over…
Saturday January 10, 2026
9:30 p.m. – 10:30 p.m.The Annoyance Theatre
851 W. Belmont Ave.Sports & Recreation
McCormick Tribune Ice Rink
Ice skating at the McCormick Tribune Ice Rink in Millennium Park begins Nov. 21 (weather permitting). Admission to the ice rink will be free, but…
Sunday January 11, 2026
11:00 a.m. – 10:30 p.m.Millennium Park
201 E Randolph StMusic & Comedy, Theatre & Performing Arts
Wheel of Improv
Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…
Sunday January 11, 2026
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St.Sports & Recreation
McCormick Tribune Ice Rink
Ice skating at the McCormick Tribune Ice Rink in Millennium Park begins Nov. 21 (weather permitting). Admission to the ice rink will be free, but…
Monday January 12, 2026
11:00 a.m. – 10:30 p.m.Millennium Park
201 E Randolph StSports & Recreation
McCormick Tribune Ice Rink
Ice skating at the McCormick Tribune Ice Rink in Millennium Park begins Nov. 21 (weather permitting). Admission to the ice rink will be free, but…
Tuesday January 13, 2026
11:00 a.m. – 10:30 p.m.Millennium Park
201 E Randolph StMusic & Comedy
Tuesday Good Show
Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…
Tuesday January 13, 2026
7:00 p.m. – 8:30 p.m.The Gallery Cabaret
2020 N Oakley AveSports & Recreation
McCormick Tribune Ice Rink
Ice skating at the McCormick Tribune Ice Rink in Millennium Park begins Nov. 21 (weather permitting). Admission to the ice rink will be free, but…
Wednesday January 14, 2026
11:00 a.m. – 10:30 p.m.Millennium Park
201 E Randolph StMusic & Comedy, Theatre & Performing Arts
Hooch & Holler Comedy Show
Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…
Wednesday January 14, 2026
9:00 p.m. – 11:00 p.m.Bordel Cocktail & Cabaret
1721 W DivisionSports & Recreation
McCormick Tribune Ice Rink
Ice skating at the McCormick Tribune Ice Rink in Millennium Park begins Nov. 21 (weather permitting). Admission to the ice rink will be free, but…
Thursday January 15, 2026
11:00 a.m. – 10:30 p.m.Millennium Park
201 E Randolph StMusic & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…
Thursday January 15, 2026
7:00 p.m. – 10:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphMusic & Comedy, Theatre & Performing Arts
Dumb and Drummer
Chicago’s best comedians doing their best material over live jazz! Every third Thursday at The Lincoln Lodge Theatre, Hosted by Jamaal Sanders, Hunter Hirsch, and…
Thursday January 15, 2026
7:30 p.m. – 9:00 p.m.The Lincoln Lodge Theater
2040 N. Milwaukee Ave.Music & Comedy, Theatre & Performing Arts
Improvsed DCOM
Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM! This All Star cast is bringing screen to stage every…
Thursday January 15, 2026
8:00 p.m. – 9:00 p.m.Malarkey Comedy Company
1501 N Kingsbury StSports & Recreation
McCormick Tribune Ice Rink
Ice skating at the McCormick Tribune Ice Rink in Millennium Park begins Nov. 21 (weather permitting). Admission to the ice rink will be free, but…
Friday January 16, 2026
11:00 a.m. – 10:30 p.m.Millennium Park
201 E Randolph StFestivals, Fairs & Special Events, Museums, Galleries & Exhibitions
Wicker Park Bucktown’s “First Fridays” Art Walk
The “First Fridays Art Walk,” organized by the Wicker Park Bucktown Chamber of Commerce, welcomes art enthusiasts to explore the neighborhoods’ vibrant arts scene. All…
Friday January 16, 2026
6:00 p.m. – 8:00 p.m.Jackson Junge Gallery
1389 N Milwaukee AveMusic & Comedy, Theatre & Performing Arts
The Infinite Wrench
Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…
Friday January 16, 2026
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.

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