They Might Be Giants – The Bigger Show Tour
May1
Music & Comedy

They Might Be Giants – The Bigger Show Tour

They Might Be Giants are scheduled to perform a three-night residency in Chicago from Friday, May 1, through Sunday, May 3, 2026. These are their…

Friday, May 1st
8:00 p.m.11:00 p.m.
The Vic Theatre
3145 N. Sheffield
Voila: The Improvised Musical
May1
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 1st
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
May1
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 1st
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The 8th Dwarf
May2
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 2nd
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
Out Here
May2
Theatre & Performing Arts

Out Here

Life happens outside of your comfort zone. Out Here is a world-premiere musical, a thrilling collaboration between Court Theatre and the University of Chicago, and an intimate…

Saturday, May 2nd
2:00 p.m.4:00 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Windfall
May2
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 2nd
3:00 p.m.5:00 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
The Infinite Wrench
May2
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 2nd
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Matteo Lane – We Gotta Catch Up! Tour
May2
Music & Comedy

Matteo Lane – We Gotta Catch Up! Tour

Matteo Lane is bringing his much‑anticipated “We Gotta Catch Up!” comedy tour to Chicago, performing at the historic The Chicago Theatre on May 2, 2026 at 7:00 PM. Hailing from the Chicago area,…

Saturday, May 2nd
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
The Great Gatsby
May2
Theatre & Performing Arts

The Great Gatsby

THE PARTY’S ROARING IN CHICAGO! THE GREAT GATSBY is a “Broadway extravaganza that explodes with life and energy” (Entertainment Weekly). Based on the classic American novel…

Saturday, May 2nd
7:00 p.m.9:30 p.m.
Cadillac Palace Theatre
151 W. Randolph St. , Chicago, IL, 60601
Baby Wants Candy! The Original Completely Improvised Musical
May2
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 2nd
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May2
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 2nd
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
The Improvised Shakespeare Company®
May2
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 2nd
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Out Here
May2
Theatre & Performing Arts

Out Here

Life happens outside of your comfort zone. Out Here is a world-premiere musical, a thrilling collaboration between Court Theatre and the University of Chicago, and an intimate…

Saturday, May 2nd
7:30 p.m.9:30 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Windfall
May2
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 2nd
7:30 p.m.9:30 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Covenant
May2
May31
Theatre & Performing Arts

Covenant

“Everybody got a secret.” Expect one devilish twist after another in Covenant, a mythic and suspenseful new play hailed as “blackout-and-blood-curdling-scream deliciousness” (New York Magazine),…

Saturday, May 2nd
7:30 p.m.Sunday, May 31st
2:00 p.m.
Goodman Owen Theatre
170 N. Dearborn, Chicago, IL, 60601
The Lincoln Lodge
May2
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 2nd
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Katt Williams – Heaven On Earth Tour
May2
Music & Comedy

Katt Williams – Heaven On Earth Tour

On the heels of his explosive Netflix comedy special, WOKE FOKE, critically acclaimed comedian Katt Williams announces the HEAVEN ON EARTH TOUR. The upcoming tour…

Saturday, May 2nd
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St,
Il Volo: North American 2026 Tour
May2
Music & Comedy

Il Volo: North American 2026 Tour

Renowned Italian vocal trio IL Volo will perform live at Rosemont Theatre on May 2, 2026.

Saturday, May 2nd
8:00 p.m.11:00 p.m.
Rosemont Theatre
They Might Be Giants – The Bigger Show Tour
May2
Music & Comedy

They Might Be Giants – The Bigger Show Tour

They Might Be Giants are scheduled to perform a three-night residency in Chicago from Friday, May 1, through Sunday, May 3, 2026. These are their…

Saturday, May 2nd
8:00 p.m.11:00 p.m.
The Vic Theatre
3145 N. Sheffield
Secret Sketch Show
May2
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 2nd
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
May2
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 2nd
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The 8th Dwarf
May3
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…

Sunday, May 3rd
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
Out Here
May3
Theatre & Performing Arts

Out Here

Life happens outside of your comfort zone. Out Here is a world-premiere musical, a thrilling collaboration between Court Theatre and the University of Chicago, and an intimate…

Sunday, May 3rd
2:00 p.m.4:00 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Windfall
May3
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,…

Sunday, May 3rd
3:00 p.m.5:00 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614