Brian Regan Live!
Jan17
Music & Comedy

Brian Regan Live!

Acclaimed comedian Brian Regan is scheduled to perform in Chicago on Saturday, January 17, 2026, at The Chicago Theatre.

Saturday January 17, 2026
8:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
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
Filament Theatre presents RAIN: for babies and their carers
Jan18
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…

Sunday January 18, 2026
9:00 a.m.2:00 p.m.
Filament Theatre
4041 N. Milwaukee Ave., Chicago, IL, 60641
Julia Bullock and Seth Parker Woods with Conor Hanick
Jan18
Music & Comedy

Julia Bullock and Seth Parker Woods with Conor Hanick

Two-time GRAMMY-nominated cellist Seth Parker Woods propels classical music into the future through projects that delve deep into our cultural fabric. GRAMMY-winning American classical singer…

Sunday January 18, 2026
3:00 p.m.4:30 p.m.
Reva and David – Logan Center for the Arts
915 E 60th St
Amadeus
Jan18
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…

Sunday January 18, 2026
3:00 p.m.5:00 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
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
The Unknown Variable by Nahal Navidar
Jan18
Theatre & Performing Arts

The Unknown Variable by Nahal Navidar

Momentary Theatre is proud to announce the world premiere of The Unknown Variable, written by Nahal Navidar, and directed by Jacob C. Shuler. The production…

Sunday January 18, 2026
7:00 p.m.9:00 p.m.
1133 W Catalpa
1133 W Catalpa Ave
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
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
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 Unknown Variable by Nahal Navidar
Jan19
Theatre & Performing Arts

The Unknown Variable by Nahal Navidar

Momentary Theatre is proud to announce the world premiere of The Unknown Variable, written by Nahal Navidar, and directed by Jacob C. Shuler. The production…

Monday January 19, 2026
7:00 p.m.9:00 p.m.
1133 W Catalpa
1133 W Catalpa Ave
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
Amadeus
Jan20
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 20, 2026
7:30 p.m.9:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
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
Amadeus
Jan21
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…

Wednesday January 21, 2026
7:30 p.m.10:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
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