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
Voila: The Improvised Musical
May22
Music & 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,
Hitch*Cocktails
May22
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.
Stargazers Adventure Club
May23
Music & 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.
Sueños Music Festival 2026
May23
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…

Saturday, May 23rd
12:00 p.m.11:00 p.m.
Grant Park
337 E Randolph St
Dinner Detective Murder Mystery Show
May23
Music & 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 St
Slide Away
May23
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…

Saturday, May 23rd
6:00 p.m.11:00 p.m.
The Infinite Wrench
May23
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…

Saturday, May 23rd
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Baby Wants Candy! The Original Completely Improvised Musical
May23
Music & Comedy, Theatre & Performing Arts

Baby Wants Candy! The Original Completely Improvised Musical

“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…

Saturday, May 23rd
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May23
Music & Comedy, Theatre & Performing Arts

Clued In

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…

Saturday, May 23rd
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Secret Sketch Show
May23
Music & Comedy

Secret Sketch Show

Shhhhh! It’s a secret! Don’t tell anyone but your favorite iO performers are hosting a wild night of variety and sketch. Secret sketch show is…

Saturday, May 23rd
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
May23
Music & Comedy, Theatre & Performing Arts

Best Of Annoyance Sketch

Enjoy the best sketch comedy Chicago has to offer! The Annoyance Theatre has been at the crux of the comedy scene in Chicago for over…

Saturday, May 23rd
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Sueños Music Festival 2026
May24
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…

Sunday, May 24th
12:00 p.m.11:00 p.m.
Grant Park
337 E Randolph St
Thornhill – The Mercia Tour
May24
Music & Comedy

Thornhill – The Mercia Tour

Australian alternative metal band Thornhill is scheduled to perform in Chicago on May 24 as part of The Mercia Tour. Supporting Acts: 156/Silence, Fox Lake,…

Sunday, May 24th
6:00 p.m.11:00 p.m.
The Vic Theatre
3145 N. Sheffield
Wheel of Improv
May24
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 24th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Tuesday Good Show
May26
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 26th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Comic Court: Chicago’s #1 Comedy Court Show
May26
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Comic Court: Chicago’s #1 Comedy Court Show

Order in the court!Comic Court is back at The Lincoln Lodge every 2nd & 4th Tuesday at 9PM. Comedians argue ridiculous cases like actual lawyers,…

Tuesday, May 26th
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
A$AP Rocky – Don’t Be Dumb World Tour 2026
May27
Music & Comedy

A$AP Rocky – Don’t Be Dumb World Tour 2026

Hip-hop artist A$AP Rocky is scheduled to kick off his 42-date “Don’t Be Dumb World Tour” in Chicago on Wednesday, May 27, 2026. This tour…

Wednesday, May 27th
7:30 p.m.10:30 p.m.
United Center
1901 W Madison St,
Hooch & Holler Comedy Show
May27
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 27th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
May27
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 27th
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.