The Phantom of the Opera
Dec31
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, December 31st
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
A Christmas Carol
Dec31
Theatre & Performing Arts

A Christmas Carol

“I will honor Christmas in my heart, and try to keep it all the year.” Rediscover a Dickens’ classic with an adaptation that “makes you…

Wednesday, December 31st
2:00 p.m.
Goodman Albert Theatre
170 N. Dearborn, Chicago, IL, 60601
Teatro Zinzanni
Dec31
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…

Wednesday, December 31st
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Amadeus
Dec31
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…

Wednesday, December 31st
7:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
New Year’s Eve Spectacular Spectacular! at Stars & Garters
Dec31
Jan1
Theatre & Performing Arts

New Year’s Eve Spectacular Spectacular! at Stars & Garters

Chicago’s recently opened premier retro entertainment venue, Stars & Garters, 3914 N. Clark St., is pleased to present the New Year’s Eve Spectacular Spectacular! Celebrations…

Wednesday December 31, 2025
8:00 p.m.Thursday January 1, 2026
3:00 a.m.
Stars & Garters
3914 N. Clark St.
Hooch & Holler Comedy Show
Dec31
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, December 31st
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Phantom of the Opera
Jan1
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 1, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Stars & Garters Presents “Stars & Garters After Dark”
Jan1
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 1, 2026
7:00 p.m.9:30 p.m.
Stars and Garters Club
3914 N Clark St
Teatro Zinzanni
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…

Thursday January 1, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Amadeus
Jan1
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…

Thursday January 1, 2026
7:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Improvsed DCOM
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…

Thursday January 1, 2026
8:00 p.m.9:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Phantom of the Opera
Jan2
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 2, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Comedy Hour at Annoyance Theatre
Jan2
Jan3
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 2, 2026
12:00 a.m.Saturday January 3, 2026
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
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.