Wheel of Improv
May17
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 17th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Julio Torres Live
May17
Music & Comedy

Julio Torres Live

Julio Torres is scheduled to perform in Chicago on Sunday, May 17, 2026, for his “Works in Progress” show.

Sunday, May 17th
7:30 p.m.9:30 p.m.
Park West
322 W Armitage Ave
Good Kid – Can We Hang Out? 2026 Tour
May17
Music & Comedy

Good Kid – Can We Hang Out? 2026 Tour

Toronto indie rock band Good Kid /w special guest Inoha will perform live at Chicago’s Riviera Theatre on May 17, 2026.

Sunday, May 17th
7:30 p.m.10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Bruno Mars – The Romantic Tour
May17
Music & Comedy

Bruno Mars – The Romantic Tour

16-time Grammy winner Bruno Mars /w special guests Leon Thomas & DJ Pee.Wee will perform live at Chicago’s Soldier Field on May 16-17, 2026.

Sunday, May 17th
7:30 p.m.11:30 p.m.
Soldier Field
1410 Special Olympics Drive
moonwatchers
May17
Jun3
Music & Comedy, Theatre & Performing Arts

moonwatchers

It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…

Sunday, May 17th
8:00 p.m.Wednesday, June 3rd
2:30 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Magic Mondays
May18
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, May 18th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Chaos and Carnage: Thy Art Is Murder, Carnifex & Bodysnatcher
May19
Music & Comedy

Chaos and Carnage: Thy Art Is Murder, Carnifex & Bodysnatcher

The Chaos and Carnage 2026 tour will be at the Ramova Theatre in Chicago on Tuesday, May 19, 2026. This year’s installment features a massive…

Tuesday, May 19th
4:45 p.m.10:00 p.m.
Ramova Theatre
3520 S. Halsted St.
Tuesday Good Show
May19
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 19th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Joe Jackson – Hope and Fury Tour
May19
Music & Comedy

Joe Jackson – Hope and Fury Tour

Joe Jackson and his band are scheduled for a two-night residency at Park West in Chicago on Tuesday, May 19, and Wednesday, May 20, 2026.…

Tuesday, May 19th
7:30 p.m.10:30 p.m.
Park West
322 W Armitage Ave
Khalid – It’s Always Summer Somewhere 2026 Tour
May20
Music & Comedy

Khalid – It’s Always Summer Somewhere 2026 Tour

Multi-platinum artist Khalid /w special guest Lauv will perform live at Chicago’s Huntington Bank Pavilion at Northerly Island on May 20, 2026.

Wednesday, May 20th
7:30 p.m.10:30 p.m.
Chet Faker – A Love For Strangers World Tour
May20
Music & Comedy

Chet Faker – A Love For Strangers World Tour

Chet Faker is scheduled to perform in Chicago on Wednesday, May 20, 2026, as part of his A Love For Strangers World Tour. This tour…

Wednesday, May 20th
7:30 p.m.10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Joe Jackson – Hope and Fury Tour
May20
Music & Comedy

Joe Jackson – Hope and Fury Tour

Joe Jackson and his band are scheduled for a two-night residency at Park West in Chicago on Tuesday, May 19, and Wednesday, May 20, 2026.…

Wednesday, May 20th
7:30 p.m.10:30 p.m.
Park West
322 W Armitage Ave
Hooch & Holler Comedy Show
May20
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 20th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
May20
Music & Comedy, Theatre & Performing Arts

The Fizz Show

Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…

Wednesday, May 20th
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
Morgan’s Laugh Lounge
May21
Music & Comedy

Morgan’s Laugh Lounge

Laugh your way into your new favorite Thursday tradition at Morgan’s Laugh Lounge, Chicago’s newest comedy hotspot. Every Thursday night from 6:00–9:30 PM, the lounge…

Thursday, May 21st
7:00 p.m.8:30 p.m.
Morgan’s On Fulton
950 W Fulton Market
Dark Side of the Pillow Sketch Comedy Show
May21
Music & Comedy, Theatre & Performing Arts

Dark Side of the Pillow Sketch Comedy Show

The thoughts you have at 2 a.m.? We put them on stage. Looking for a night out that feels unmistakably Chicago? Dark Side of the…

Thursday, May 21st
7:30 p.m.8:30 p.m.
The De Matt Theater at The Second City
230 W North Ave
Dumb and Drummer
May21
Music & Comedy, Theatre & Performing Arts

Dumb and Drummer

Chicago’s best comedians doing their best material over live jazz! Every third Thursday at The Lincoln Lodge Theatre, Hosted by Jamaal Sanders, Hunter Hirsch, and…

Thursday, May 21st
7:30 p.m.9:00 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Concrete Boys – It’s Us Vol. 2 Tour
May21
Music & Comedy

Concrete Boys – It’s Us Vol. 2 Tour

Concrete Boys is scheduled to perform in Chicago on Thursday, May 21, 2026, as part of their “It’s Us Vol. 2 Tour”.

Thursday, May 21st
7:30 p.m.10:30 p.m.
Park West
322 W Armitage Ave
Slide Away
May22
Music & Comedy

Slide Away

The Slide Away 2026 festival will take place in Chicago over two nights, Friday, May 22, and Saturday, May 23, 2026. The festival features a…

Friday, May 22nd
6:00 p.m.11:00 p.m.
Kid Cudi – Rebel Ragers Tour
May22
Music & Comedy

Kid Cudi – Rebel Ragers Tour

Grammy-winning rapper and songwriter Kid Cudi is scheduled to perform in the Chicago area on Friday, May 22, 2026, as part of The Rebel Ragers…

Friday, May 22nd
6:30 p.m.10:00 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave
The Infinite Wrench
May22
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, May 22nd
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Grossman Ensemble – Illuminations
May22
Music & Comedy

Grossman Ensemble – Illuminations

The Grossman Ensemble—performing the best music you haven’t heard yet—closes the 2025-26 concert season with an energetic evening of brand-new music. Luke Poeppel conducts the…

Friday, May 22nd
7:30 p.m.9:00 p.m.
Reva and David – Logan Center for the Arts
915 E 60th St
Devil’s Daughter
May22
Music & Comedy

Devil’s Daughter

The hottest show in town, Devil’s Daughter, features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…

Friday, May 22nd
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
The Kid LAROi – A Perfect World Tour
May22
Music & Comedy

The Kid LAROi – A Perfect World Tour

The Kid LAROI will bring his A Perfect World Tour to Chicago’s The Salt Shed on Friday, May 22, 2026. This outdoor performance at the…

Friday, May 22nd
7:30 p.m.10:30 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL