ComedySportz Chicago
Jan17
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 17, 2026
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Best Of Annoyance Sketch
Jan17
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 17, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The Phantom of the Opera
Jan18
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 18, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Eureka Day
Jan18
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…

Sunday January 18, 2026
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Teatro Zinzanni
Jan18
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 18, 2026
4:00 p.m.7:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Wheel of Improv
Jan18
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 18, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
The Phantom of the Opera
Jan19
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 19, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Eureka Day
Jan19
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…

Monday January 19, 2026
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Magic Mondays
Jan19
Music & Comedy, Theatre & Performing Arts

Magic Mondays

Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…

Monday January 19, 2026
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
The Phantom of the Opera
Jan20
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 20, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Eureka Day
Jan20
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 20, 2026
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
The Phantom of the Opera
Jan21
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 21, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Eureka Day
Jan21
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 21, 2026
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Hooch & Holler Comedy Show
Jan21
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 21, 2026
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Phantom of the Opera
Jan22
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 22, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Eureka Day
Jan22
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 22, 2026
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
The Three Little Pigs at Beverly Arts Center
Jan22
Theatre & Performing Arts

The Three Little Pigs at Beverly Arts Center

Meet Roxanne, Petunia, and Babe…three Sister Piggies who set out to build their own houses.  Roxanne (the Rock’n Roll Pig) builds hers out of Sticks,…

Thursday January 22, 2026
10:30 a.m.11:30 a.m.
Beverly Arts Center of Chicago
2407 W. 111th St. , Chicago, IL, 60655
Disney On Ice: Jump In!
Jan22
Theatre & Performing Arts

Disney On Ice: Jump In!

Disney On Ice presents “Jump In!” is coming to Allstate Arena in Rosemont from January 22 – February 8 with an all-new show featuring never-before-seen…

Thursday January 22, 2026
7:00 p.m.9:00 p.m.
Allstate Arena
6920 Mannheim Road
Stars & Garters Presents “Stars & Garters After Dark”
Jan22
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 22, 2026
7:00 p.m.9:30 p.m.
Stars and Garters Club
3914 N Clark St
Teatro Zinzanni
Jan22
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 22, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Improvsed DCOM
Jan22
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 22, 2026
8:00 p.m.9:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Phantom of the Opera
Jan23
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 23, 2026
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Eureka Day
Jan23
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 23, 2026
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
Comedy Hour at Annoyance Theatre
Jan23
Jan24
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 23, 2026
12:00 a.m.Saturday January 24, 2026
1:00 a.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.