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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/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Saturday January 3, 2026
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
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
The Improvised Shakespeare Company®
Jan3
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…

Saturday January 3, 2026
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Sherlock Holmes and the Christmas Clowns
Jan3
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…

Saturday January 3, 2026
7:30 p.m.9:30 p.m.
City Lit Theater
1020 W. Bryn Mawr, Chicago, IL, 60660
The Lincoln Lodge
Jan3
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…

Saturday January 3, 2026
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
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.
The Phantom of the Opera
Jan4
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…

Sunday January 4, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Sherlock Holmes and the Christmas Clowns
Jan4
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…

Sunday January 4, 2026
3:00 p.m.5:00 p.m.
City Lit Theater
1020 W. Bryn Mawr, Chicago, IL, 60660
Amadeus
Jan4
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…

Sunday January 4, 2026
7:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
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.
The Phantom of the Opera
Jan5
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…

Monday January 5, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
The Phantom of the Opera
Jan6
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…

Tuesday January 6, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
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
The Phantom of the Opera
Jan7
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…

Wednesday January 7, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
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
The Phantom of the Opera
Jan8
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…

Thursday January 8, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Stars & Garters Presents “Stars & Garters After Dark”
Jan8
Theatre & Performing Arts

Stars & Garters Presents “Stars & Garters After Dark”

Chicago’s brand new Stars & Garters, 3914 N Clark St, presents Stars & Garters After Dark, every Thursday at 7 p.m. in the Rouge Room.…

Thursday January 8, 2026
7:00 p.m.9:30 p.m.
Stars and Garters Club
3914 N Clark St
Teatro Zinzanni
Jan8
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…

Thursday January 8, 2026
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
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 Phantom of the Opera
Jan9
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…

Friday January 9, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
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