Amadeus
Dec28
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, December 28th
7:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Manual Cinema’s Christmas Carol
Dec28
Theatre & Performing Arts

Manual Cinema’s Christmas Carol

Manual Cinema’s awe-inspiring, one-of-a-kind rendition of the Dickens classic returns to the Studebaker Theater this holiday season! Avowed holiday skeptic Aunt Trudy has been reluctantly…

Sunday, December 28th
7:30 p.m.
Fine Arts Building | Studebaker Theater
410 South Michigan Avenue
Wheel of Improv
Dec28
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, December 28th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
‘Twas The Night Before… By Cirque du Soleil
Dec28
Theatre & Performing Arts

‘Twas The Night Before… By Cirque du Soleil

Due to overwhelming success, the celebrated holiday theatrical ‘Twas the Night Before… by Cirque du Soleil is returning to The Chicago Theatre for a limited…

Sunday, December 28th
7:30 p.m.9:30 p.m.
Chicago Theatre
Chicago’s Best Stand Up
Dec28
Music & Comedy

Chicago’s Best Stand Up

Welcome to Chicago’s Best Stand Up at The Laugh Factory – Chicago, featuring some of the city’s finest comedians. Get ready for a night of…

Sunday, December 28th
9:00 p.m.11:00 p.m.
The Laugh Factory
175 N Broadway
Chicago’s Best Stand Up
Dec28
Music & Comedy

Chicago’s Best Stand Up

Welcome to Chicago’s Best Stand Up at The Laugh Factory – Chicago! Join us on December 28, 2025, at 9:00 PM for a night of…

Sunday, December 28th
9:00 p.m.11:00 p.m.
The Laugh Factory
175 N Broadway
The Phantom of the Opera
Dec29
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, December 29th
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
A Christmas Carol
Dec29
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…

Monday, December 29th
2:00 p.m.
Goodman Albert Theatre
170 N. Dearborn, Chicago, IL, 60601
Raheem DeVaughn – 20 Lessons of Love Tour
Dec29
Music & Comedy

Raheem DeVaughn – 20 Lessons of Love Tour

Get ready for a night of soulful vibrancy as multi‑platinum R&B artist Raheem DeVaughn heads to Chicago. Known for his silky vocals and heartfelt lyrics,…

Monday, December 29th
6:00 p.m.11:30 p.m.
City Winery
1200 West Randolph Street
Clayton Horwitz at Zanies Chicago – Live Comedy Taping!
Dec29
Music & Comedy, Theatre & Performing Arts

Clayton Horwitz at Zanies Chicago – Live Comedy Taping!

CLAY HORWITZ is an NYC comedian originally from Chicago. He is the star and writer of the show Clay’s Feast on Amazon Prime Video, and…

Monday, December 29th
7:00 p.m.8:30 p.m.
Zanies Comedy Night Club
1548 North Wells Street
Teatro Zinzanni
Dec29
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…

Monday, December 29th
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Amadeus
Dec29
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…

Monday, December 29th
7:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Stand Ups Sit Down Comedy Showcase
Dec29
Music & Comedy

Stand Ups Sit Down Comedy Showcase

Welcome to The Laugh Factory in Chicago, Illinois – the ultimate hotspot for comedy lovers! Join us on December 29, 2025, at 8:00 PM for…

Monday, December 29th
8:00 p.m.10:00 p.m.
The Laugh Factory
175 N Broadway
The Phantom of the Opera
Dec30
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, December 30th
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
A Christmas Carol
Dec30
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…

Tuesday, December 30th
2:00 p.m.
Goodman Albert Theatre
170 N. Dearborn, Chicago, IL, 60601
Improvised Christmas Carol
Dec30
Music & Comedy, Theatre & Performing Arts

Improvised Christmas Carol

In a cuckoo-bananas world, sometimes we all just need a good ‘ol fashion morality check. It’s time for Ebenezer Scrooge to get another supernatural wake-up…

Tuesday, December 30th
7:00 p.m.8:00 p.m.
The Second City
230 W North Ave., 2nd Floor
Tuesday Good Show
Dec30
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, December 30th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Amadeus
Dec30
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…

Tuesday, December 30th
7:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Fresh Faces of Chicago
Dec30
Music & Comedy

Fresh Faces of Chicago

Welcome to The Ground Name, your go-to destination for live events in Chicago, Illinois! Join us on December 30, 2025, at 7:30 PM for an…

Tuesday, December 30th
7:30 p.m.9:30 p.m.
The Laugh Factory
175 N Broadway
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
Jeff Dunham: Artificial Intelligence Tour
Dec31
Music & Comedy

Jeff Dunham: Artificial Intelligence Tour

Comedian and ventriloquist Jeff Dunham lights up the stage at Allstate Arena in Rosemont, IL, on December 31, 2025, as part of his Artificial Intelligence Tour. His infamous characters…

Wednesday, December 31st
3:00 p.m.5:00 p.m.
Allstate Arena
6920 Mannheim Road
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
Dru Hill: Tell Me it’s New Years Eve!
Dec31
Music & Comedy

Dru Hill: Tell Me it’s New Years Eve!

Get ready, Chicago — the smooth‑and‑soulful harmony of Dru Hill is hitting the Windy City! Known for their R&B anthems like In My Bed and How Deep Is Your Love, Dru Hill…

Wednesday, December 31st
7:00 p.m.11:30 p.m.
City Winery
1200 West Randolph Street