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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 AveMusic & 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.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 60611Music & 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 StatesMusic & 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 StMusic & 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.…
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 AvenueMusic & 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, ILMusic & 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.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.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 RoadMusic & 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 StMusic & 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 AveMusic & 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
9:00 p.m. – 10:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy
The Regulars
A cult favorite candle-lit comedy show soirée! Doors: 8:30 Start: 9:00 SHOW: Enjoy a piece of news roundup in the style of “Weekend Update” that…
Friday, May 22nd
9:00 p.m. – 10:30 p.m.The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United StatesMusic & Comedy, Theatre & Performing Arts
Voila: The Improvised Musical
iO Chicago presents: a fully made-up, off-off-off Broadway style musical every Friday at 10pm in the Fremont Theater. Spend your Friday night with us. See…
Friday, May 22nd
10:00 p.m. – 11:30 p.m.The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,Music & Comedy, Theatre & Performing Arts
Hitch*Cocktails
A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together…
Friday, May 22nd
10:00 p.m. – 11:30 p.m.Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.Music & Comedy
Laughter Hours: Late Night Jazzy-Themed Comedy Show
A late-night comedy showcase with a jazzy, lounge vibe featuring a live jazz musician and Chicago’s best comedians This is a showcase featuring some of…
Friday, May 22nd
11:00 p.m. – 11:59 p.m.The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United StatesMusic & Comedy
Stargazers Adventure Club
Blast off with Stargazers Adventure Club in Planetary Games, an interactive space spectacular where imagination fuels the fun! You’ll learn planetary facts from out-of-this-world host,…
Saturday, May 23rd
10:00 a.m. – 11:30 a.m.Stars & Garters Theater
3914 N. Clark St.Music & Comedy
Sueños Music Festival 2026
The Sueños Music Festival celebrates its fifth anniversary in Grant Park, Chicago, on Saturday, May 23, and Sunday, May 24, 2026. This Memorial Day weekend…
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,…
Saturday, May 23rd
2:30 p.m. – 5:00 p.m.Greenhouse Theater Center
2257 North Lincoln AvenueMusic & Comedy
Hecklers’ Happy Hour Comedy Show
Audiences can unleash their inner “heckler” against some of Chicago’s funniest comics in this chaotic standup showcase Hecklers’ Happy Hour aims to give audiences a…
Saturday, May 23rd
6:00 p.m. – 7:15 p.m.The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United StatesMusic & Comedy, Theatre & Performing Arts
Dinner Detective Murder Mystery Show
The Dinner Detective is an interactive true crime murder mystery show set in the present day and based on real cold cases. Feast on a…
Saturday, May 23rd
6:00 p.m. – 9:00 p.m.Courtyard by Marriott Chicago Downtown Magnificent Mile
165 E Ontario StMusic & 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…

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