Pegasus Theatre Chicago’s 39th Annual Young Playwrights Festival
Jan3
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,…

Saturday January 3, 2026
7:00 p.m.9:30 p.m.
Chicago Dramatists
1105 W. Chicago Ave. , Chicago, IL, 60642
Teatro Zinzanni
Jan3
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…

Saturday January 3, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
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
Ronnie Baker Brooks
Jan3
Music & Comedy

Ronnie Baker Brooks

Welcome to City Winery – Chicago, where the vibrant heartbeat of the city meets the soulful tunes of Ronnie Baker Brooks. Join us on January…

Saturday January 3, 2026
7:30 p.m.9:30 p.m.
city winery chicago
1200 W. Randolph Street
New Year New Show
Jan3
Music & Comedy, Theatre & Performing Arts

New Year New Show

New Year! New Show! Welcome to 2026 where the laughter runs hot and the jokes run cheap. Every week is a brand new sketch show,…

Saturday January 3, 2026
8:00 p.m.9:00 p.m.
The De Matt Theater at The Second City
230 W North Ave
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
The Cozy Cabin Tales
Jan4
Theatre & Performing Arts

The Cozy Cabin Tales

Theatre for Young Audiences @ Corn presents our newest show, perfect for young ones and the entire family! ​The Cozy Cabin Tales is a series…

Sunday January 4, 2026
11:00 a.m.12:00 p.m.
Cornservatory
4210 N Lincoln Ave
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
Teatro Zinzanni
Jan4
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…

Sunday January 4, 2026
4:00 p.m.7:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Teatro Zinzanni
Jan4
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…

Sunday January 4, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
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
Filament Theatre presents RAIN: for babies and their carers
Jan6
Theatre & Performing Arts

Filament Theatre presents RAIN: for babies and their carers

Filament Theatre (4041 N Milwaukee Ave), Chicago’s award-winning theater for young audiences on the northwest side, is delighted to premiere the North American production of…

Tuesday January 6, 2026
9:00 a.m.2:00 p.m.
Filament Theatre
4041 N. Milwaukee Ave., Chicago, IL, 60641
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
Amadeus
Jan6
Theatre & Performing Arts

Amadeus

Steppenwolf Theatre’s 50th Anniversary Season continues with Peter Shaffer’s Amadeus, extended again by popular demand. In its four-star review, The Daily Herald called it “absolutely magnificent”. “A muscular and…

Tuesday January 6, 2026
7:30 p.m.9:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614