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
OhJay Lamont & Friends at The Comedy Bar
May21
Music & Comedy

OhJay Lamont & Friends at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry OhJay Lamont, born and raised on…

Thursday, May 21st
7:00 p.m.9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
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
Cosmic Comedy Hour
May21
Music & Comedy

Cosmic Comedy Hour

Cosmic Comedy Hour is a one-hour live comedy show that combines magic, improv, and theatrical comedy into one fast-paced experience. Unlike traditional comedy shows, this…

Thursday, May 21st
8:00 p.m.9:00 p.m.
cosmic underground theater
3433 W Fullerton Ave
Late Night at The Lodge
May21
Music & Comedy

Late Night at The Lodge

Chicago’s premiere late night comedy talk show Late Night At The Lodge is the perfect mix of stand up comedy, and funny talk show banter.…

Thursday, May 21st
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
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.
Archspire – Long Roads Big Loads Tour
May22
Music & Comedy

Archspire – Long Roads Big Loads Tour

Archspire is bringing their “Long Roads Big Loads Tour” to the House of Blues Chicago on Friday, May 22, 2026. This high-velocity technical death metal…

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.
LaTrez Anderson at The Comedy Bar
May22
Music & Comedy

LaTrez Anderson at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry PLEASE NOTE: This is a special…

Friday, May 22nd
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Good: A Standup Comedy Showcase
May22
Music & Comedy

Good: A Standup Comedy Showcase

Good comedians performing good. A stand up comedy show that showcases good comedians. Hosted by Greg Kennedy. *** Special accommodations can be made for larger…

Friday, May 22nd
7:00 p.m.8:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
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.
Company
May22
Music & Comedy, Theatre & Performing Arts

Company

From musical theatre’s most renowned composer, Company is largely regarded as a trailblazer of the dark-comedy, modern-musical genre and the winner of six Tony Awards,…

Friday, May 22nd
7:30 p.m.10:00 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
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
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
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
May22
Music & Comedy, Theatre & Performing Arts

Missed Call Sketch Comedy Show

Missed Call is a premier Chicago comedy group that writes and performs an entirely new sketch show every Friday — inspired by the audience’s suggestion!

Friday, May 22nd
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Palomazo Norteno – Clase Maestra Tour
May22
Music & Comedy

Palomazo Norteno – Clase Maestra Tour

Palomazo Norteno is scheduled to perform in the Chicago area on Friday, May 22, 2026, as part of their “Clase Maestra Tour”. The concert features…

Friday, May 22nd
8:30 p.m.11:30 p.m.
Allstate Arena
6920 Mannheim Road
Honk! A Short Form Improv Show
May22
Music & Comedy, Theatre & Performing Arts

Honk! A Short Form Improv Show

Honk! is a short form, game-based improv show that asks: what good is comedy if you can’t get a little silly? Comprised of some of…

Friday, May 22nd
9:00 p.m.10:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
420 Shakespeare
May22
Music & Comedy, Theatre & Performing Arts

420 Shakespeare

4 professional actors meet to perform a Shakespeare play… but only after one of them takes at least 20mg of you know what, leading to…

Friday, May 22nd
9:00 p.m.10:30 p.m.
The De Matt Theater at The Second City
230 W North Ave