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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 AvenueTheatre & 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, 60601Music & 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. StateMusic & 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!)…
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, 60637Music & 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 AveMusic & 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…
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 AveTheatre & 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…
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 AveMusic & Comedy
Iron & Wine Live In Chicago
Indie folk songwriter Iron & Wine will perform two shows in Chicago, IL, at Thalia Hall in May 2026.
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…
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 AveTheatre & 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, 60655Theatre & 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, 60637Music & 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 ChicagoTheatre & 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, 60614Music & 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 StreetMusic & 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 DivisionTheatre & 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…
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 AveTheatre & 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, 60655Theatre & 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.…
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

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