HighQ
May3
Music & Comedy, Theatre & Performing Arts

HighQ

Is it a cannabis-themed game show or an uproarious, electively interactive live theatrical experience? Why can’t it be both? HighQ is an uplifting blend of…

Sunday, May 3rd
6:00 p.m.7:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
The Great Gatsby
May3
Theatre & Performing Arts

The Great Gatsby

THE PARTY’S ROARING IN CHICAGO! THE GREAT GATSBY is a “Broadway extravaganza that explodes with life and energy” (Entertainment Weekly). Based on the classic American novel…

Sunday, May 3rd
7:00 p.m.9:30 p.m.
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
SatchVai Band: Joe Satriani & Steve Vai & Animals As Leaders
May3
Music & Comedy

SatchVai Band: Joe Satriani & Steve Vai & Animals As Leaders

The SatchVai Band, featuring iconic rock guitarists Joe Satriani and Steve Vai, is scheduled to perform in Chicago, IL, on Sunday, May 3, 2026, as…

Sunday, May 3rd
7:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Wheel of Improv
May3
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, May 3rd
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Out Here
May3
Theatre & Performing Arts

Out Here

Life happens outside of your comfort zone. Out Here is a world-premiere musical, a thrilling collaboration between Court Theatre and the University of Chicago, and an intimate…

Sunday, May 3rd
7:30 p.m.9:30 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Caifanes: 2026 Tour
May3
Music & Comedy

Caifanes: 2026 Tour

Legendary Mexican rock band Caifanes is scheduled to perform in Chicago on Sunday, May 3, 2026.

Sunday, May 3rd
7:30 p.m.10:30 p.m.
The Riveria Theater
4746 N Racine Ave
They Might Be Giants – The Bigger Show Tour
May3
Music & Comedy

They Might Be Giants – The Bigger Show Tour

They Might Be Giants are scheduled to perform a three-night residency in Chicago from Friday, May 1, through Sunday, May 3, 2026. These are their…

Sunday, May 3rd
8:00 p.m.11:00 p.m.
The Vic Theatre
3145 N. Sheffield
Garrison Keillor – Garrison Keillor Tonight
May4
Theatre & Performing Arts

Garrison Keillor – Garrison Keillor Tonight

Author, singer, humorist, voice actor, and radio personality Garrison Keillor is scheduled to perform in Chicago on Monday, May 4, 2026, for an evening of…

Monday, May 4th
7:30 p.m.10:30 p.m.
Park West
322 W Armitage Ave
Chicago the Musical promotional image
May5
Theatre & Performing Arts

CHICAGO the Musical

CHICAGO is still the one musical with everything that makes Broadway shimmy-shake: a universal tale of fame, fortune, and all that jazz, with one showstopping…

Tuesday, May 5th
Auditorium Theatre
50 East Ida B. Wells Drive
Tuesday Good Show
May5
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, May 5th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Iron & Wine Live In Chicago
May5
Music & Comedy

Iron & Wine Live In Chicago

Indie folk songwriter Iron & Wine will perform two shows in Chicago, IL, at Thalia Hall in May 2026.

Tuesday, May 5th
8:00 p.m.11:00 p.m.
Thalia Hall
1807 South Allport Street
Chicago the Musical promotional image
May6
Theatre & Performing Arts

CHICAGO the Musical

CHICAGO is still the one musical with everything that makes Broadway shimmy-shake: a universal tale of fame, fortune, and all that jazz, with one showstopping…

Wednesday, May 6th
Auditorium Theatre
50 East Ida B. Wells Drive
The Three Little Pigs at Stahl Family Theatre
May6
Theatre & Performing Arts

The Three Little Pigs at Stahl Family Theatre

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,…

Wednesday, May 6th
10:30 a.m.11:30 a.m.
Stahl Family Theatre
5900 W Belmont Ave
Goldilocks and the Three Bears
May6
Theatre & Performing Arts

Goldilocks and the Three Bears

This musical is JUST RIGHT!  This show is based on the classic story of a young girl who ventures into the woods and stumbles on…

Wednesday, May 6th
10:30 a.m.11:30 a.m.
Beverly Arts Center of Chicago
2407 W. 111th St. , Chicago, IL, 60655
Out Here
May6
Theatre & Performing Arts

Out Here

Life happens outside of your comfort zone. Out Here is a world-premiere musical, a thrilling collaboration between Court Theatre and the University of Chicago, and an intimate…

Wednesday, May 6th
7:30 p.m.9:30 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
NewDad
May6
Music & Comedy

NewDad

Welcome to the iconic Metro Chicago, where on May 6, 2026, the indie-rock sensation NewDad will be taking the stage at 7:30 PM. Hailing from…

Wednesday, May 6th
7:30 p.m.9:30 p.m.
Metro Chicago
Windfall
May6
Theatre & Performing Arts

Windfall

This is a story about money. Don’t let them fool you otherwise. When a father loses his child in a clash with the local police,…

Wednesday, May 6th
7:30 p.m.9:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Iron & Wine Live In Chicago
May6
Music & Comedy

Iron & Wine Live In Chicago

Indie folk songwriter Iron & Wine will perform two shows in Chicago, IL, at Thalia Hall in May 2026.

Wednesday, May 6th
8:00 p.m.11:00 p.m.
Thalia Hall
1807 South Allport Street
Hooch & Holler Comedy Show
May6
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, May 6th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Chicago the Musical promotional image
May7
Theatre & Performing Arts

CHICAGO the Musical

CHICAGO is still the one musical with everything that makes Broadway shimmy-shake: a universal tale of fame, fortune, and all that jazz, with one showstopping…

Thursday, May 7th
Auditorium Theatre
50 East Ida B. Wells Drive
The Three Little Pigs at Stahl Family Theatre
May7
Theatre & Performing Arts

The Three Little Pigs at Stahl Family Theatre

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, May 7th
8:00 a.m.11:30 a.m.
Stahl Family Theatre
5900 W Belmont Ave
Goldilocks and the Three Bears
May7
Theatre & Performing Arts

Goldilocks and the Three Bears

This musical is JUST RIGHT!  This show is based on the classic story of a young girl who ventures into the woods and stumbles on…

Thursday, May 7th
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”
May7
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, May 7th
7:00 p.m.9:30 p.m.
Stars and Garters Club
3914 N Clark St
Out Here
May7
Theatre & Performing Arts

Out Here

Life happens outside of your comfort zone. Out Here is a world-premiere musical, a thrilling collaboration between Court Theatre and the University of Chicago, and an intimate…

Thursday, May 7th
7:30 p.m.9:30 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637