Gus Constantellis at The Comedy Bar
May8
Music & Comedy

Gus Constantellis at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Gus Constantellis (he/they) is a gay,…

Friday, May 8th
9:00 p.m.10:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Voila: The Improvised Musical
May8
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 8th
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
May8
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 8th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Chicago the Musical promotional image
May9
Theatre & Performing Arts

CHICAGO the Musical

CHICAGO is still the one musical with everything that makes Broadway shimmy-shake: a universal tale of fame, fortune, and all that jazz, with one showstopping…

Saturday, May 9th
Auditorium Theatre
50 East Ida B. Wells Drive
The 8th Dwarf
May9
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 9th
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
Out Here
May9
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 9th
2:00 p.m.4:00 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Sesame Street Live: Elmo’s Got The Moves
May9
Theatre & Performing Arts

Sesame Street Live: Elmo’s Got The Moves

Make unforgettable memories with your little ones at Elmo’s Got the Moves—the all-new Sesame Street Live show coming to The Chicago Theatre on Saturday, May…

Saturday, May 9th
2:00 p.m.4:00 p.m.
The Chicago Theatre
175 N. State
Disclosure: Spring 2026 North America Tour
May9
Music & Comedy

Disclosure: Spring 2026 North America Tour

Multi-Platinum duo Disclosure will perform live at The Salt Shed Outdoors on May 8-10, 2026.

Saturday, May 9th
6:30 p.m.9:30 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
The Infinite Wrench
May9
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 9th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Gus Constantellis at The Comedy Bar
May9
Music & Comedy

Gus Constantellis at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Gus Constantellis (he/they) is a gay,…

Saturday, May 9th
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Baby Wants Candy! The Original Completely Improvised Musical
May9
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 9th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May9
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 9th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
The Improvised Shakespeare Company®
May9
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 9th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Out Here
May9
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 9th
7:30 p.m.9:30 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
The Lincoln Lodge
May9
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 9th
8:00 p.m.9:30 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Alejandro Fernandez – de Rey a Rey Tour
May9
Music & Comedy

Alejandro Fernandez – de Rey a Rey Tour

Alejandro Fernández is bringing his de Rey a Rey tour, a tribute to the music of his late father, the legendary Vicente Fernández, to Allstate…

Saturday, May 9th
8:30 p.m.11:30 p.m.
Allstate Arena
6920 Mannheim Road
Gus Constantellis at The Comedy Bar
May9
Music & Comedy

Gus Constantellis at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Gus Constantellis (he/they) is a gay,…

Saturday, May 9th
9:00 p.m.10:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Secret Sketch Show
May9
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 9th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
May9
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 9th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Chicago the Musical promotional image
May10
Theatre & Performing Arts

CHICAGO the Musical

CHICAGO is still the one musical with everything that makes Broadway shimmy-shake: a universal tale of fame, fortune, and all that jazz, with one showstopping…

Sunday, May 10th
Auditorium Theatre
50 East Ida B. Wells Drive
The 8th Dwarf
May10
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 10th
2:00 p.m.3:00 p.m.
Bughouse Theater
1910 West Irving Park Road
Out Here
May10
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 10th
2:00 p.m.4:00 p.m.
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Windfall
May10
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 10th
3:00 p.m.5:00 p.m.
Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614
Disclosure: Spring 2026 North America Tour
May10
Music & Comedy

Disclosure: Spring 2026 North America Tour

Multi-Platinum duo Disclosure will perform live at The Salt Shed Outdoors on May 8-10, 2026.

Sunday, May 10th
6:30 p.m.9:30 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL