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
Theater of the Mind
May23
Theatre & Performing Arts

Theater of the Mind

Now through July 12, 2026 Multiple experiences per day at the Reid Murdoch Building, 333 N LaSalle Visit TheateroftheMindChicago.com for dates, times, and tickets Created…

Saturday, May 23rd
Reid Murdoch Building – 333 N LaSalle
333 N LaSalle
Goodnight Moon
May23
Theatre & Performing Arts

Goodnight Moon

This musical based on Margaret Wise Brown’s beloved children’s book is drenched in primary colors that pay homage to Clement Hurd’s vivid illustrations in an…

Saturday, May 23rd
9:30 a.m.10:30 a.m.
Chicago Children’s Theatre
100 S Racine Ave
The Hula-Hoopin’ Queen
May23
Theatre & Performing Arts

The Hula-Hoopin’ Queen

CHICAGO – YPT’s acclaimed 4th season concludes with Thelma Lynn Goodin’s joyous celebration of family, friends, and community in a close-knit Harlem neighborhood! Evanston playwright…

Saturday, May 23rd
11:00 a.m.12:15 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
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
Covenant
May23
Theatre & Performing Arts

Covenant

BY YORK WALKER DIRECTED BY MALKIA STAMPLEY “Everybody got a secret.” Expect one devilish twist after another in Covenant, a mythic and suspenseful new play hailed…

Saturday, May 23rd
2:00 p.m.3:30 p.m.
Goodman Theatre
170 N. Dearborn St.
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
For Gustave
May23
Theatre & Performing Arts

For Gustave

On the Spot Theatre Company is delighted to present the world premiere of For Gustave, a new drama about French Impressionist Gustave Caillebotte. For Gustave…

Saturday, May 23rd
2:00 p.m.4:00 p.m.
6205 N Sheridan Rd,
6205 N Sheridan Rd,
An Enemy of the People
May23
Theatre & Performing Arts

An Enemy of the People

An award-winning new take on the historic masterwork about citizens standing up to power.  When a respected doctor in small-town Norway makes a deadly discovery…

Saturday, May 23rd
2:00 p.m.4:00 p.m.
TimeLine Theatre Company
5035 N Broadway
Metropolis Performing Arts Centre Presents “The Wedding Singer”
May23
Theatre & Performing Arts

Metropolis Performing Arts Centre Presents “The Wedding Singer”

Metropolis Performing Arts Centre, located in the heart of downtown Arlington Heights, 111 W. Campbell St., is proud to announce the cast and creative team…

Saturday, May 23rd
2:00 p.m.5:00 p.m.
Metropolis Performing Arts Centre
111 W Campbell Street
Company
May23
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 Avenue
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
Wild Door Theater Presents “Maybe Tomorrow”
May23
Theatre & Performing Arts

Wild Door Theater Presents “Maybe Tomorrow”

Wild Door Theater presents the Midwest premiere of Maybe Tomorrow, a darkly funny and unsettling new play by Max Mondi and directed by Andrew Gallant,…

Saturday, May 23rd
3:00 p.m.5:00 p.m.
Athenaeum Center for Thought & Culture
2936 N. Southport Ave. , Chicago, IL, 60657
Wild Door Theater Presents “Maybe Tomorrow”
May23
Theatre & Performing Arts

Wild Door Theater Presents “Maybe Tomorrow”

Wild Door Theater presents the Midwest premiere of Maybe Tomorrow, a darkly funny and unsettling new play by Max Mondi and directed by Andrew Gallant,…

Saturday, May 23rd
3:00 p.m.5:00 p.m.
Athenaeum Center for Thought & Culture
2936 N. Southport Ave. , Chicago, IL, 60657
Cosmic Underground Show
May23
Theatre & Performing Arts

Cosmic Underground Show

Fridays and Saturdays, the Cosmic Underground Show blasts off for a 90-minute immersive comedy, magic, and mind-reading show. Cosmic founders Harrison Lampert (a quirky sleight-of-hand…

Saturday, May 23rd
4:30 p.m.6:00 p.m.
cosmic underground theater
3433 W Fullerton Ave
[producing body] Presents “Spaceman”
May23
Theatre & Performing Arts

[producing body] Presents “Spaceman”

[producingbody] is pleased to announce the Chicago premiere of Spaceman, by Leegrid Stevens and directed by Eric Slater, May 19 – June 13, at The…

Saturday, May 23rd
4:30 p.m.6:30 p.m.
The Edge Off Broadway Theatre
1133 W Catalpa Ave.
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
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
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.
FreakShow & Tell
May23
Theatre & Performing Arts

FreakShow & Tell

21+ ONLY Brianna Wellen, Chicago Reader: Sideshow entertainer Thom Britton’s solo show is part performance, part demonstration. Britton is a charismatic performer who appears genuinely…

Saturday, May 23rd
7:00 p.m.8:30 p.m.
Stars & Garters Theater
3914 N. Clark St.
Gee’s Bend
May23
Theatre & Performing Arts

Gee’s Bend

GEE’S BEND is the story of the Pettway women, quilters from the isolated community of Gee’s Bend, Alabama. Beginning in 1939, the play follows Alice, her…

Saturday, May 23rd
7:00 p.m.8:30 p.m.
Fleetwood-Jourdain Theatre in the Noyes Cultural Arts Center
927 Noyes Steet