Skip to consent to cookiesSkip navigation
Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Check out what's happening all around Chicago.

ComedySportz Chicago
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…

Friday January 2, 2026
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Teatro Zinzanni
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…

Friday January 2, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Devil’s Daughter
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.…

Friday January 2, 2026
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
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!

Friday January 2, 2026
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Trapped in a Musical – an improvised musical
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…

Friday January 2, 2026
9:00 p.m.10:00 p.m.
Voila: The Improvised Musical
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…

Friday January 2, 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,
Hitch*Cocktails
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…

Friday January 2, 2026
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
ComedySportz Chicago
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…

Saturday January 3, 2026
6:00 p.m.7:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Infinite Wrench
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…

Saturday January 3, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Teatro Zinzanni
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…

Saturday January 3, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Baby Wants Candy! The Original Completely Improvised Musical
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…

Saturday January 3, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
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…

Saturday January 3, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Ronnie Baker Brooks
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…

Saturday January 3, 2026
7:30 p.m.9:30 p.m.
city winery chicago
1200 W. Randolph Street
ComedySportz Chicago
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…

Saturday January 3, 2026
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Best Of Annoyance Sketch
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…

Saturday January 3, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Teatro Zinzanni
Jan4
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…

Sunday January 4, 2026
4:00 p.m.7:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Wheel of Improv
Jan4
Music & 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 4, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Tuesday Good Show
Jan6
Music & 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 6, 2026
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Hooch & Holler Comedy Show
Jan7
Music & 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 7, 2026
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Johnny Hamcheck at The Comedy Bar
Jan8
Music & Comedy

Johnny Hamcheck at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry A night of standup comedy and…

Thursday January 8, 2026
7:00 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Teatro Zinzanni
Jan8
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…

Thursday January 8, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Improvsed DCOM
Jan8
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 8, 2026
8:00 p.m.9:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Infinite Wrench
Jan9
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…

Friday January 9, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
ComedySportz Chicago
Jan9
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…

Friday January 9, 2026
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
bean-night

Explore Chicago hotels, flights, deals, and more

Plan your trip

Expedia
Expedia
Expedia
Expedia

CTA Newsletter

Chicago Newsletter

Stay in the know

Sign up

OVG25_enews_cover_for website footer

Chicago Visitors Guide

Start planning today

Get the guide