Raheem DeVaughn – 20 Lessons of Love Tour
Dec26
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,…

Friday, December 26th
6:00 p.m.11:30 p.m.
City Winery
1200 West Randolph Street
Charles Dickens Begrudgingly Performs ‘A Christmas Carol’ Again
Dec26
Theatre & Performing Arts

Charles Dickens Begrudgingly Performs ‘A Christmas Carol’ Again

Clownshow is proud to present Blake Montgomery in his award-winning solo production Charles Dickens Begrudgingly Performs ‘A Christmas Carol’ Again, at Theater Wit, 1229 W.…

Friday, December 26th
7:00 p.m.
Theater Wit
The Infinite Wrench
Dec26
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, December 26th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Who’s Holiday! at Theater Wit
Dec26
Theatre & Performing Arts

Who’s Holiday! at Theater Wit

Christmas Day is in our grasp. Why the vodka? Glad you asked! The tot from The Grinch has grown, you see! She’s cursing and drinking,…

Friday, December 26th
7:00 p.m.8:00 p.m.
Theater Wit
ComedySportz Chicago
Dec26
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, December 26th
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
ComedySportz Chicago
Dec26
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, December 26th
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Chicago Bulls vs. Philadelphia 76ers
Dec26
Friday, December 26th
7:00 p.m.8:30 p.m.
United Center
1901 W Madison St,
First Date Comedy Gameshow
Dec26
Music & Comedy

First Date Comedy Gameshow

Welcome to The Laugh Factory – Chicago, the ultimate destination for a night of laughter in the heart of Chicago, Illinois. Join us on December…

Friday, December 26th
7:00 p.m.9:00 p.m.
The Laugh Factory
175 N Broadway
Teatro Zinzanni
Dec26
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, December 26th
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Krampus: The Fright Before Christmas
Dec26
Festivals, Fairs & Special Events, Tours & Attractions

Krampus: The Fright Before Christmas

We have transformed our haunted house into a Christmas wonderland, although it won’t be all glitter and snowflakes. You better watch out. You better not…

Friday, December 26th
7:00 p.m.10:00 p.m.
13th Floor Chicago
5050 River Rd
Amadeus
Dec26
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, December 26th
7:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Manual Cinema’s Christmas Carol
Dec26
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…

Friday, December 26th
7:30 p.m.
Fine Arts Building | Studebaker Theater
410 South Michigan Avenue
The Long Christmas Dinner
Dec26
Theatre & Performing Arts

The Long Christmas Dinner

THE LONG CHRISTMAS DINNER – nine decades long in just one 75-minute act – showcases the lives of several generations of the Bayard family. Wilder…

Friday, December 26th
7:30 p.m.8:45 p.m.
Bramble Arts Loft
The Improvised Shakespeare Company®
Dec26
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, December 26th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
It’s a Wonderful Life: Live in Chicago!
Dec26
Theatre & Performing Arts

It’s a Wonderful Life: Live in Chicago!

George Bailey – the Everyman from small town Bedford Falls whose dreams of escape and adventure were stopped by family obligation and civic duty –…

Friday, December 26th
7:30 p.m.9:00 p.m.
American Blues Theater
5627 N Lincoln Blvd
Vibe Check Comedy Show – Chicago Edition
Dec26
Music & Comedy

Vibe Check Comedy Show – Chicago Edition

VIBE CHECK is a nationally touring comedy showcase filled with good vibes & the hottest young comics in the country. Featured in Time Out!! Vibe…

Friday, December 26th
7:30 p.m.9:00 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
‘Twas The Night Before… By Cirque du Soleil
Dec26
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…

Friday, December 26th
7:30 p.m.9:30 p.m.
Chicago Theatre
Sherlock Holmes and the Christmas Clowns
Dec26
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, December 26th
7:30 p.m.9:30 p.m.
City Lit Theater
1020 W. Bryn Mawr, Chicago, IL, 60660
Oil Lamp Presents “It’s A Wonderful Life: A Live Radio Play”
Dec26
Theatre & Performing Arts

Oil Lamp Presents “It’s A Wonderful Life: A Live Radio Play”

Oil Lamp Theater is proud to present the final production in its 2025 season, It’s A Wonderful Life: A Live Radio Play, November 20 –…

Friday, December 26th
7:30 p.m.10:00 p.m.
Oil Lamp Theater
1723 Glenview Rd, Glenview, IL, 60025
Devil’s Daughter
Dec26
Music & Comedy

Devil’s Daughter

The hottest show in town Devil’s Daughter features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…

Friday, December 26th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
Dec26
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, December 26th
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The Lincoln Lodge
Dec26
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, December 26th
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Halloween Chicago Ghost Tour & Hunt: Lincoln Park Hauntings by American Ghost Walks
Dec26
Festivals, Fairs & Special Events, Tours & Attractions

Halloween Chicago Ghost Tour & Hunt: Lincoln Park Hauntings by American Ghost Walks

Join American Ghost Walks on a spine-chilling Chicago Ghost Tour & Ghost Hunt in Lincoln Park, known for its eerie hauntings and chilling history. Dive…

Friday, December 26th
8:00 p.m.10:00 p.m.
Meeting Point: In front of the Chicago History Museum
1601 N Clark St.
Trapped in a Musical – an improvised musical
Dec26
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, December 26th
9:00 p.m.10:00 p.m.