The Infinite Wrench
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…

Friday January 2, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
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
1501 N. Kingsbury St.
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
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Jan2
Theatre & Performing Arts

Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival

Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen.  For nearly four decades,…

Friday January 2, 2026
7:00 p.m.9:30 p.m.
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
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
Amadeus
Jan2
Theatre & Performing Arts

Amadeus

Vienna: a cacophony of music and intrigue. The emperor’s composer, Antonio Salieri, holds court until the flamboyant entrance of Wolfgang Amadeus Mozart: prodigy and wild…

Friday January 2, 2026
7:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
The Improvised Shakespeare Company®
Jan2
Theatre & Performing Arts

The Improvised Shakespeare Company®

The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago, now in its 19th year! Join us for an evening of…

Friday January 2, 2026
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Sherlock Holmes and the Christmas Clowns
Jan2
Theatre & Performing Arts

Sherlock Holmes and the Christmas Clowns

Sherlock Holmes and Dr. Watson travel to the country to spend the holidays with an old army comrade of Watson’s. What they don’t know is…

Friday January 2, 2026
7:30 p.m.9:30 p.m.
City Lit Theater
1020 W. Bryn Mawr, Chicago, IL, 60660
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.
The Lincoln Lodge
Jan2
Theatre & Performing Arts

The Lincoln Lodge

The Lincoln Lodge stand-up comedy and variety showcase plays every Friday and Saturday night in Chicago’s glamorous Logan Square! In addition to The Lodge’s rotating…

Friday January 2, 2026
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee 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.
The Phantom of the Opera
Jan3
Theatre & Performing Arts

The Phantom of the Opera

THE BRILLIANT ORIGINAL RETURNS “MORE SPECTACULAR THAN EVER” – Sunday Express The Phantom is back to thrill audiences once again! Cameron Mackintosh presents a revitalized…

Saturday January 3, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
New Year New Show
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,…

Saturday January 3, 2026
8:00 a.m.5:00 p.m.
The De Matt Theater at The Second City
230 W North Ave
The Cozy Cabin Tales
Jan3
Theatre & Performing Arts

The Cozy Cabin Tales

Theatre for Young Audiences @ Corn presents our newest show, perfect for young ones and the entire family! ​The Cozy Cabin Tales is a series…

Saturday January 3, 2026
11:00 a.m.12:00 p.m.
Cornservatory
4210 N Lincoln Ave
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Jan3
Theatre & Performing Arts

Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival

Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen.  For nearly four decades,…

Saturday January 3, 2026
2:30 p.m.4:00 p.m.
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
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.
Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Jan3
Theatre & Performing Arts

Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival

Pegasus Theatre Chicago presents the 39th Annual Young Playwrights Festival, January 1 – 24, 2026 at Chicago Dramatists, 798 N. Aberdeen.  For nearly four decades,…

Saturday January 3, 2026
7:00 p.m.9:30 p.m.
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
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
Amadeus
Jan3
Theatre & Performing Arts

Amadeus

Vienna: a cacophony of music and intrigue. The emperor’s composer, Antonio Salieri, holds court until the flamboyant entrance of Wolfgang Amadeus Mozart: prodigy and wild…

Saturday January 3, 2026
7:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
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