Mandatory Photo Credit: Abel Arciniega :: @tequilagraphics

Upcoming Chicago Events

Name: The Improvised Shakespeare Company®
Start: 2026-05-22T19:30:00-05:00
End: 2026-05-22T21:00:00-05:00
Location: iO Theater

Check out what's happening all around Chicago.

May 20, 2026: May20
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…
Loop
Event details
Wednesday, May 20th
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Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
May20
Theatre & Performing Arts
The Three Little Pigs at Stahl Family Theatre
Meet Roxanne, Petunia, and Babe…three Sister Piggies who set out to build their own houses. Roxanne (the Rock’n Roll Pig) builds hers out of Sticks,…
Event details
Wednesday, May 20th
10:30 a.m. – 11:30 a.m.
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Stahl Family Theatre
5900 W Belmont Ave
May20
Theatre & Performing Arts
Goldilocks and the Three Bears
This musical is JUST RIGHT! This show is based on the classic story of a young girl who ventures into the woods and stumbles on…
Event details
Wednesday, May 20th
10:30 a.m. – 11:30 a.m.
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Beverly Arts Center of Chicago
2407 W. 111th St. , Chicago, IL, 60655
May20
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,…
Lincoln Park
Event details
Wednesday, May 20th
2:00 p.m. – 4:00 p.m.
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Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
May20
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,…
Lincoln Park
Event details
Wednesday, May 20th
7:30 p.m. – 9:30 p.m.
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Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
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.
South Loop
Event details
Wednesday, May 20th
7:30 p.m. – 10:30 p.m.
Huntington Bank Pavilion at Northerly Island
1300 S. Linn White Dr.
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…
Event details
Wednesday, May 20th
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield
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.…
Event details
Wednesday, May 20th
7:30 p.m. – 10:30 p.m.
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Park West
322 W Armitage Ave
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…
Event details
Wednesday, May 20th
9:00 p.m. – 11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
May 21, 2026: May21
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…
Loop
Event details
Thursday, May 21st
See all events in series
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
May21
Theatre & Performing Arts
The Three Little Pigs at Stahl Family Theatre
Meet Roxanne, Petunia, and Babe…three Sister Piggies who set out to build their own houses. Roxanne (the Rock’n Roll Pig) builds hers out of Sticks,…
Event details
Thursday, May 21st
10:30 a.m. – 11:30 a.m.
See all events in series
Stahl Family Theatre
5900 W Belmont Ave
May21
Theatre & Performing Arts
Goldilocks and the Three Bears
This musical is JUST RIGHT! This show is based on the classic story of a young girl who ventures into the woods and stumbles on…
Event details
Thursday, May 21st
10:30 a.m. – 11:30 a.m.
See all events in series
Beverly Arts Center of Chicago
2407 W. 111th St. , Chicago, IL, 60655
May21
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…
Loop
Event details
Thursday, May 21st
5:00 p.m. – 7:00 p.m.
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CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
May21
Theatre & Performing Arts
Stars & Garters Presents “Stars & Garters After Dark”
Chicago’s brand new Stars & Garters, 3914 N Clark St, presents Stars & Garters After Dark, every Thursday at 7 p.m. in the Rouge Room.…
Event details
Thursday, May 21st
7:00 p.m. – 9:30 p.m.
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Stars and Garters Club
3914 N Clark St
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…
Event details
Thursday, May 21st
7:30 p.m. – 9:00 p.m.
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The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
May21
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,…
Lincoln Park
Event details
Thursday, May 21st
7:30 p.m. – 9:30 p.m.
See all events in series
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
May 22, 2026: May22
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…
Loop
Event details
Friday, May 22nd
See all events in series
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
May22
May23
Theatre & Performing Arts
Comedy Hour at Annoyance Theatre
Each week, Chicago comics bring the freshest, most experimental new material to the Annoyance for the Comedy Hour. The weekly show is an eclectic mix…
Lakeview
Event details
Friday, May 22nd
12:00 a.m. – Saturday, May 23rd
1:00 a.m.
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Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
May22
Theatre & Performing Arts
The Three Little Pigs at Stahl Family Theatre
Meet Roxanne, Petunia, and Babe…three Sister Piggies who set out to build their own houses. Roxanne (the Rock’n Roll Pig) builds hers out of Sticks,…
Event details
Friday, May 22nd
10:30 a.m. – 11:30 a.m.
See all events in series
Stahl Family Theatre
5900 W Belmont Ave
May22
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…
Loop
Event details
Friday, May 22nd
5:00 p.m. – 7:00 p.m.
See all events in series
CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602
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…
Uptown
Event details
Friday, May 22nd
6:00 p.m. – 11:00 p.m.
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Aragon Ballroom
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…
Event details
Friday, May 22nd
6:30 p.m. – 10:00 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave
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…
Andersonville
Event details
Friday, May 22nd
7:00 p.m. – 8:00 p.m.
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The Neo-Futurist Theater
5153 N. Ashland Ave.
May22
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…
Lincoln Park
Event details
Friday, May 22nd
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.