John Cusack with a Screening of Grosse Pointe Blank
Jun13
Music & Comedy

John Cusack with a Screening of Grosse Pointe Blank

An Evening with John Cusack and Screening of Grosse Pointe Blank is scheduled to take place in Chicago on Saturday, June 13, 2026. The event…

Saturday, June 13th
7:30 p.m.9:30 p.m.
Auditorium
50 East Ida B. Wells Drive
Secret Sketch Show
Jun13
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, June 13th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Jun13
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, June 13th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Amyl and The Sniffers: North American 2026 Tour
Jun14
Music & Comedy

Amyl and The Sniffers: North American 2026 Tour

Australian punk rock firebrands Amyl and The Sniffers /w special guests Party Dozen and L7 will perform live at Chicago’s The Salt Shed Outdoors on…

Sunday, June 14th
7:00 p.m.10:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
Stand By Me: The Film and Its Stars 40 Years Later
Jun14
Music & Comedy

Stand By Me: The Film and Its Stars 40 Years Later

To celebrate the 40th anniversary of the classic coming-of-age film, the special event “Stand By Me: The Film and Its Stars 40 Years Later” is…

Sunday, June 14th
7:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Wheel of Improv
Jun14
Music & Comedy, Theatre & Performing Arts

Wheel of Improv

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…

Sunday, June 14th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Magic Mondays
Jun15
Music & Comedy, Theatre & Performing Arts

Magic Mondays

Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…

Monday, June 15th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Tuesday Good Show
Jun16
Music & Comedy

Tuesday Good Show

Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…

Tuesday, June 16th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Jazzin’ at the Shedd
Jun17
Museums, Galleries & Exhibitions, Music & Comedy

Jazzin’ at the Shedd

Live jazz revels at Shedd Aquarium! Join us for the popular midweek  Jazzin’ at the Shedd series with unforgettable evenings of music, mingling and marine life.…

Wednesday, June 17th
5:00 p.m.10:00 p.m.
Shedd Aquarium
1200 S. Lake Shore Dr.
Hooch & Holler Comedy Show
Jun17
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…

Wednesday, June 17th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
Jun17
Music & Comedy, Theatre & Performing Arts

The Fizz Show

Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…

Wednesday, June 17th
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
Morgan’s Laugh Lounge
Jun18
Music & Comedy

Morgan’s Laugh Lounge

Laugh your way into your new favorite Thursday tradition at Morgan’s Laugh Lounge, Chicago’s newest comedy hotspot. Every Thursday night from 6:00–9:30 PM, the lounge…

Thursday, June 18th
7:00 p.m.8:30 p.m.
Morgan’s On Fulton
950 W Fulton Market
Dumb and Drummer
Jun18
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…

Thursday, June 18th
7:30 p.m.9:00 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
The Kevin Langue Show Live
Jun18
Music & Comedy

The Kevin Langue Show Live

The Kevin Langue Show: Live! is coming to Chicago on Thursday, June 18, 2026. Known as the “Home of the World’s Best Guesser,” the live…

Thursday, June 18th
8:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Carín León – De Sonora Para El Mundo Tour 2026
Jun18
Music & Comedy

Carín León – De Sonora Para El Mundo Tour 2026

Mexican regional music superstar Carín León is scheduled to perform at the Allstate Arena in Rosemont, IL, on Thursday, June 18, 2026, as part of…

Thursday, June 18th
8:00 p.m.11:00 p.m.
Allstate Arena
6920 Mannheim Road
Enter Shikari: North America 2026 Tour
Jun18
Music & Comedy

Enter Shikari: North America 2026 Tour

Enter Shikari is bringing their “North America 2026” tour to Chicago for a headline performance in June 2026.

Thursday, June 18th
8:00 p.m.11:00 p.m.
Thalia Hall
1807 South Allport Street
Morgan Wallen Live In Chicago – Still The Problem Tour 2026
Jun19
Music & Comedy

Morgan Wallen Live In Chicago – Still The Problem Tour 2026

Country megastar Morgan Wallen brings the Still The Problem Tour to Chicago for two back-to-back nights at Soldier Field  on June 19 and 20, 2026,…

Friday, June 19th
5:30 p.m.10:00 p.m.
Soldier Field
1410 Special Olympics Drive
The Marcus King Band – The Darling Blue Tour Pt. 2
Jun19
Music & Comedy

The Marcus King Band – The Darling Blue Tour Pt. 2

The Marcus King Band is scheduled to perform in Chicago, IL, on Friday, June 19, 2026, at The Salt Shed Outdoors. This show is part…

Friday, June 19th
6:30 p.m.9:30 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
The Pussycat Dolls – PCD Forever Tour
Jun19
Music & Comedy

The Pussycat Dolls – PCD Forever Tour

The Pussycat Dolls are scheduled to perform in Chicago (Tinley Park), IL, on Friday, June 19, 2026, as part of their highly anticipated “PCD Forever…

Friday, June 19th
6:30 p.m.10:00 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave
The Infinite Wrench
Jun19
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…

Friday, June 19th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Devil’s Daughter
Jun19
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, June 19th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Connor Price & Nic D – ICONIC Tour
Jun19
Music & Comedy

Connor Price & Nic D – ICONIC Tour

Connor Price is performing in Chicago on Friday, June 19, 2026, as part of his ICONIC Tour alongside Nic D.

Friday, June 19th
7:30 p.m.10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Devil’s Daughter
Jun19
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, June 19th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Honk! A Short Form Improv Show
Jun19
Music & Comedy, Theatre & Performing Arts

Honk! A Short Form Improv Show

Honk! is a short form, game-based improv show that asks: what good is comedy if you can’t get a little silly? Comprised of some of…

Friday, June 19th
9:00 p.m.10:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St