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.
Windfall
May22
Theatre & 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,…

Friday, May 22nd
7:30 p.m.9:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
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.
3 Stages of Love Part 2: Simple Love/Unperfect Actor
May22
Theatre & Performing Arts

3 Stages of Love Part 2: Simple Love/Unperfect Actor

Love always makes for a good story because some part of it is always relatable. And what better way to explore all the various sides…

Friday, May 22nd
8:00 p.m.9:00 p.m.
Mrs. Murphy & Sons Irish Bistro
3905 N Lincoln Ave
The Lincoln Lodge
May22
Theatre & Performing Arts

The Lincoln Lodge

The Lincoln Lodge stand-up comedy and variety showcase plays every Friday and Saturday night in Chicago’s glamorous Logan Square! In addition to The Lodge’s rotating…

Friday, May 22nd
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee 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
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.
Les Misérables
May23
Theatre & Performing Arts

Les Misérables

STILL THE WORLD’S MOST POPULAR MUSICAL Cameron Mackintosh’s acclaimed production of Alain Boublil and Claude-Michel Schönberg’s Tony Award-winning musical phenomenon, Les Misérables, makes a triumphant return…

Saturday, May 23rd
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
The 8th Dwarf
May23
Theatre & Performing Arts

The 8th Dwarf

Binkley, an outsider dwarf from the Kingdom of Magical Land, is quiet, timid and scared of the dark — not exactly the best characteristics for…

Saturday, May 23rd
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
Mirror of Most Value: A Ms. Marvel Play
May23
Theatre & Performing Arts

Mirror of Most Value: A Ms. Marvel Play

Kamala Khan was an average high school student until a mysterious mist unlocked her shape-shifting superpowers and changed everything. When her obsession with building her…

Saturday, May 23rd
2:00 p.m.4:00 p.m.
Merle Reskin Theatre
60 E. Balbo, Chicago, IL, 60605
Windfall
May23
Theatre & 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,…

Saturday, May 23rd
3:00 p.m.5:00 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Spamalot
May23
Theatre & Performing Arts

Spamalot

THE SHOW THAT SET BROADWAY BACK 1,000 YEARS…RETURNS! TOURING ACROSS AMERICA THE TONY AWARD-WINNING BEST MUSICAL COMEDY MONTY PYTHON’S SPAMALOT Peter Marks of The Washington…

Saturday, May 23rd
5:00 p.m.7:00 p.m.
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
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
The Improvised Shakespeare Company®
May23
Theatre & Performing Arts

The Improvised Shakespeare Company®

The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago, now in its 19th year! Join us for an evening of…

Saturday, May 23rd
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Windfall
May23
Theatre & 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,…

Saturday, May 23rd
7:30 p.m.9:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
The Lincoln Lodge
May23
Theatre & Performing Arts

The Lincoln Lodge

The Lincoln Lodge stand-up comedy and variety showcase plays every Friday and Saturday night in Chicago’s glamorous Logan Square! In addition to The Lodge’s rotating…

Saturday, May 23rd
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
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.