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ComedySportz Chicago
Jan10
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 10, 2026
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Best Of Annoyance Sketch
Jan10
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 10, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The Phantom of the Opera
Jan11
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 11, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Wheel of Improv
Jan11
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 11, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
The Phantom of the Opera
Jan12
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 12, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
The Phantom of the Opera
Jan13
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 13, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Eureka Day
Jan13
Theatre & Performing Arts

Eureka Day

Chicago’s acclaimed TimeLine Theatre Company returns to the Broadway Playhouse (following previous hit productions OSLO and THE LEHMAN TRILOGY)! At Berkeley, California’s ultra-progressive Eureka Day…

Tuesday January 13, 2026
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
The Phantom of the Opera
Jan14
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 14, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Eureka Day
Jan14
Theatre & Performing Arts

Eureka Day

Chicago’s acclaimed TimeLine Theatre Company returns to the Broadway Playhouse (following previous hit productions OSLO and THE LEHMAN TRILOGY)! At Berkeley, California’s ultra-progressive Eureka Day…

Wednesday January 14, 2026
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Hooch & Holler Comedy Show
Jan14
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 14, 2026
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Phantom of the Opera
Jan15
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 15, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Eureka Day
Jan15
Theatre & Performing Arts

Eureka Day

Chicago’s acclaimed TimeLine Theatre Company returns to the Broadway Playhouse (following previous hit productions OSLO and THE LEHMAN TRILOGY)! At Berkeley, California’s ultra-progressive Eureka Day…

Thursday January 15, 2026
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Stars & Garters Presents “Stars & Garters After Dark”
Jan15
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 15, 2026
7:00 p.m.9:30 p.m.
Stars and Garters Club
3914 N Clark St
Teatro Zinzanni
Jan15
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 15, 2026
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Dumb and Drummer
Jan15
Music & 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.
Improvsed DCOM
Jan15
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 St
The Phantom of the Opera
Jan16
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 16, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Eureka Day
Jan16
Theatre & Performing Arts

Eureka Day

Chicago’s acclaimed TimeLine Theatre Company returns to the Broadway Playhouse (following previous hit productions OSLO and THE LEHMAN TRILOGY)! At Berkeley, California’s ultra-progressive Eureka Day…

Friday January 16, 2026
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Comedy Hour at Annoyance Theatre
Jan16
Jan17
Theatre & Performing Arts

Comedy Hour at Annoyance Theatre

Each week, Chicago comics bring the freshest, most experimental new material to the Annoyance for the Comedy Hour. The weekly show is an eclectic mix…

Friday January 16, 2026
12:00 a.m.Saturday January 17, 2026
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Infinite Wrench
Jan16
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 16, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
ComedySportz Chicago
Jan16
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 16, 2026
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
ComedySportz Chicago
Jan16
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 16, 2026
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Teatro Zinzanni
Jan16
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…

Friday January 16, 2026
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Improvised Shakespeare Company®
Jan16
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 16, 2026
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
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