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January 1, 2026: Jan1
Music & Comedy
Dru Hill: Tell Me it’s New Years Eve!
Get ready, Chicago — the smooth‑and‑soulful harmony of Dru Hill is hitting the Windy City! Known for their R&B anthems like In My Bed and How Deep Is Your Love, Dru Hill…
West Loop
Event details
Thursday, January 1st
6:00 p.m. – 11:30 p.m.
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City Winery
1200 West Randolph Street
Jan1
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…
Event details
Thursday, January 1st
7:00 p.m. – 10:00 p.m.
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Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Jan1
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…
Event details
Thursday, January 1st
8:00 p.m. – 9:00 p.m.
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Malarkey Comedy Company
1501 N Kingsbury St
January 2, 2026: Jan2
Music & 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…
Andersonville
Event details
Friday, January 2nd
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
Jan2
Music & 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…
Event details
Friday, January 2nd
7:00 p.m. – 8:30 p.m.
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Malarkey Comedy
1501 N. Kingsbury St.
Jan2
Music & 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…
Event details
Friday, January 2nd
7:00 p.m. – 8:30 p.m.
See all events in series
Malarkey Comedy Company
1501 N Kingsbury St
Jan2
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…
Event details
Friday, January 2nd
7:00 p.m. – 10:00 p.m.
See all events in series
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Jan2
Music & Comedy
Devil’s Daughter
The hottest show in town, Devil’s Daughter, features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…
Lincoln Park
Event details
Friday, January 2nd
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Jan2
Music & Comedy
Devil’s Daughter
The hottest show in town Devil’s Daughter features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…
Lincoln Park
Event details
Friday, January 2nd
8:00 p.m. – 9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Jan2
Music & Comedy, Theatre & Performing Arts
Missed Call Sketch Comedy Show
Missed Call is a premier Chicago comedy group that writes and performs an entirely new sketch show every Friday — inspired by the audience’s suggestion!
Lakeview
Event details
Friday, January 2nd
8:00 p.m. – 9:00 p.m.
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The Annoyance Theatre
851 W. Belmont Ave.
Jan2
Music & Comedy, Theatre & Performing Arts
Trapped in a Musical – an improvised musical
Trapped in a Musical is a completely improvised Broadway-style show created before your very eyes. It’s the opening and closing night of a brand new…
Lakeview
Event details
Friday, January 2nd
9:00 p.m. – 10:00 p.m.
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Malarkey Comedy, Home of ComedySportz Chicago
929 W. Belmont Ave.
Jan2
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…
Event details
Friday, January 2nd
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,
Jan2
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…
Lakeview
Event details
Friday, January 2nd
10:00 p.m. – 11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
January 3, 2026: Jan3
Music & Comedy, Theatre & Performing Arts
New Year New Show
New Year! New Show! Welcome to 2026 where the laughter runs hot and the jokes run cheap. Every week is a brand new sketch show,…
Event details
Saturday, January 3rd
8:00 a.m. – 5:00 p.m.
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The De Matt Theater at The Second City
230 W North Ave
Jan3
Music & 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…
Event details
Saturday, January 3rd
6:00 p.m. – 7:30 p.m.
See all events in series
Malarkey Comedy Company
1501 N Kingsbury St
Jan3
Music & Comedy
Circuit Breakers II
Circuit Breakers returns with another all-star line-up of some of the hottest comics on the Chicago comedy circuit! This edition of Circuit Breakers promises an…
Event details
Saturday, January 3rd
6:30 p.m. – 7:30 p.m.
BABS Comedy Club
7316 Madison St
Jan3
Music & 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…
Andersonville
Event details
Saturday, January 3rd
7:00 p.m. – 8:00 p.m.
See all events in series
The Neo-Futurist Theater
5153 N. Ashland Ave.
Jan3
Music & Comedy, Theatre & Performing Arts
Teatro Zinzanni
Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…
Event details
Saturday, January 3rd
7:00 p.m. – 10:00 p.m.
See all events in series
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Jan3
Music & 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…
Old Town
Event details
Saturday, January 3rd
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Jan3
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…
Old Town
Event details
Saturday, January 3rd
7:30 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St., Theater on the Second Floor
Jan3
Music & Comedy
Ronnie Baker Brooks
Welcome to City Winery – Chicago, where the vibrant heartbeat of the city meets the soulful tunes of Ronnie Baker Brooks. Join us on January…
Event details
Saturday, January 3rd
7:30 p.m. – 9:30 p.m.
city winery chicago
1200 W. Randolph Street
Jan3
Music & Comedy, Theatre & Performing Arts
New Year New Show
New Year! New Show! Welcome to 2026 where the laughter runs hot and the jokes run cheap. Every week is a brand new sketch show,…
Event details
Saturday, January 3rd
8:00 p.m. – 9:00 p.m.
See all events in series
The De Matt Theater at The Second City
230 W North Ave
Jan3
Music & 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…
Event details
Saturday, January 3rd
8:00 p.m. – 9:30 p.m.
See all events in series
Malarkey Comedy Company
1501 N Kingsbury St
Jan3
Music & 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…
Lakeview
Event details
Saturday, January 3rd
9:30 p.m. – 10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.

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