Upcoming Chicago Events
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Music & Comedy
Music & Comedy
The Armando Diaz
It’s the best comedy show in the city. Created in 1995 by iO alum Armando Diaz, Armando is a historic improvisational form where actors improvise a series…
Music & Comedy
Best of the Second City
Find out for yourself why The Second City has been the first name in laughter for over sixty years! From the stages that launched the…
Music & Comedy
Maplewood Comedy Showcase
LOGAN SQUARE—YOUR MONDAY NIGHT JUST GOT FUNNIER. 🎤 The Maplewood Comedy Showcase returns Monday, September 14, with a stacked lineup hosted by comedian Michael Meyers!…
Music & Comedy, Theatre & Performing Arts
NICE SHIRT: The Second City Grad Revue
Original sketch comedy and improv from The Second City Conservatory’s graduating class, live at the Chicago e.t.c. Theater in Old Town. NICE SHIRT is the…
Music & Comedy
$10 Improv Night
All the cool kids stay out late on a school night! Join new teams as they deliver a short and sweet show filled with laughter…
Music & Comedy
The 11pm Show
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
Music & Comedy
Tomato Throw Show at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Join us for the most fun…
Music & Comedy
Jay Park – Serenades & Body Rolls World Tour
Korean-American artist Jay Park will perform live in Chicago on Tuesday, September 15, 2026, as part of his Serenades & Body Rolls World Tour. The…
Music & Comedy
The 11pm Show
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
Music & Comedy
Respawn Improv with Blue.0
A weekly improv show hosted by Blue.0 and featuring a rotating cast of indie teams formed right here at The iO Theater! Each Wednesday at…
Music & Comedy
Suicideboys – Grey Day Tour 2026
$uicideboy$ are scheduled to perform in Tinley Park, IL, on Wednesday, September 16, 2026, as part of their Grey Day Tour 2026. The concert will…
Music & Comedy
Wil Milz at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry MR. PACK YOU UP!!! Wil Milz…
Music & Comedy, Theatre & Performing Arts
RAD. a fun show.
A RAD alt comedy show, featuring standup, music, sketch, clown, drag, and WEIRD SH*T. Operating out of the basements of local comic book stores since…
Music & Comedy
Brandon Flowers – 2026 North American Tour
The Killers frontman Brandon Flowers will perform live in Chicago on Wednesday, September 16, 2026 at the Riviera Theatre. The highly anticipated concert is part…
Music & Comedy
Play Time
A showcase of 3 short plays by select writing teams and featuring a cast of iO Theater performers. It’s experimental, it’s follow-the-fun, it’s Play Time. Plays…
Music & Comedy
Chicago’s Favorite Brick Nerd, Will Quam, joins Chicago’s Late Night Talk Show
Get the late night talk show experience without heading to NYC or LA. The Not That Late Show is a POC- and queer-led late-night talk…
Music & Comedy
Altin Gun: North American Tour 2026
Altın Gün is scheduled to perform in Chicago on Wednesday, September 16, 2026, as part of their North American Tour 2026. The tour celebrates their…
Music & Comedy
Tinlicker – 2026 North American Tour
Tinlicker is kicking off their North American tour at the House of Blues Chicago on Wednesday, September 16, 2026.
Music & Comedy
Carly Pearce – Honest Woman: Up Close Tour
Grammy-winning country artist Carly Pearce is bringing her “Honest Woman: Up Close” tour to Chicago for two back-to-back performances on Wednesday, September 16, 2026 and…
Music & Comedy
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,…
Music & Comedy
The 11pm Show
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
Music & Comedy
Best of Chicago Comedy – Chicago
Get ready for a night of laughter and unforgettable performances at the “Best of Chicago Comedy – Chicago”! Join us at The Foundation Room at…
Music & Comedy
The 27th Anniversary Englewood Jazz Festival
The 27th Anniversary Englewood Jazz Festival free events to be held September 17-19, 2026 at Hamilton Park, Chicago CELEBRATING YOUNG MUSICIANS OF THE NEXT GENERATION, …
Music & Comedy
BigfaybO at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Bigfayb0 is a popular content creator…
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