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Upcoming Chicago Events

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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
Tuesday Good Show
Jan20
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 20, 2026
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
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
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/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Thursday January 22, 2026
7:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
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.
Peter Pan at Chicago Kids Company
Jan23
Theatre & Performing Arts

Peter Pan at Chicago Kids Company

Follow Peter Pan and Tinkerbell to Neverland! The adventures are endless in a world of pirates and mayhem. Let your imagination fly to a place…

Friday January 23, 2026
10:30 a.m.11:30 a.m.
Stahl Family Theatre
5900 W Belmont Ave
The Three Little Pigs at Beverly Arts Center
Jan23
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,…

Friday January 23, 2026
10:30 a.m.11:30 a.m.
Beverly Arts Center of Chicago
2407 W. 111th St. , Chicago, IL, 60655
Wicker Park Bucktown’s “First Fridays” Art Walk
Jan23
Festivals, Fairs & Special Events, Museums, Galleries & Exhibitions

Wicker Park Bucktown’s “First Fridays” Art Walk

The “First Fridays Art Walk,” organized by the Wicker Park Bucktown Chamber of Commerce, welcomes art enthusiasts to explore the neighborhoods’ vibrant arts scene. All…

Friday January 23, 2026
6:00 p.m.8:00 p.m.
Jackson Junge Gallery
1389 N Milwaukee Ave
The Infinite Wrench
Jan23
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 23, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
ComedySportz Chicago
Jan23
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 23, 2026
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
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