Chrono Trigger Orchestra Concert: Melodies Across Time
Oct14
Music & Comedy

Chrono Trigger Orchestra Concert: Melodies Across Time

The legendary adventure transcends time once more—now through music. In celebration of Chrono Trigger’s enduring legacy, the timeless journey beloved by generations is brought back…

Wednesday, October 14th
8:00 p.m.10:00 p.m.
Auditorium
50 East Ida B. Wells Drive
Hooch & Holler Comedy Show
Oct14
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, October 14th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
Oct14
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, October 14th
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
Morgan’s Laugh Lounge
Oct15
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, October 15th
7:00 p.m.8:30 p.m.
Morgan’s On Fulton
950 W Fulton Market
Dumb and Drummer
Oct15
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, October 15th
7:30 p.m.9:00 p.m.
The Lincoln Lodge Theater
2040 N. Milwaukee Ave.
Daði Freyr – Too Much, Not Enough Tour
Oct15
Music & Comedy

Daði Freyr – Too Much, Not Enough Tour

Daði Freyr is scheduled to perform in Chicago on Thursday, October 15, 2026, as part of his “Too Much, Not Enough” North American Tour. Special…

Thursday, October 15th
7:30 p.m.10:30 p.m.
The Vic Theatre
3145 N. Sheffield
The Infinite Wrench
Oct16
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, October 16th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Devil’s Daughter
Oct16
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, October 16th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Brad Williams: The Tall Tales Tour
Oct16
Music & Comedy

Brad Williams: The Tall Tales Tour

Brad Williams will bring the Tall Tales Tour to The Chicago Theatre on Friday, October 16.

Friday, October 16th
7:30 p.m.9:30 p.m.
The Chicago Theatre
175 N. State
Devil’s Daughter
Oct16
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, October 16th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Honk! A Short Form Improv Show
Oct16
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, October 16th
9:00 p.m.10:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Voila: The Improvised Musical
Oct16
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, October 16th
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
Oct16
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, October 16th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Stargazers Adventure Club
Oct17
Music & Comedy

Stargazers Adventure Club

Blast off with Stargazers Adventure Club in Planetary Games, an interactive space spectacular where imagination fuels the fun! You’ll learn planetary facts from out-of-this-world host,…

Saturday, October 17th
10:00 a.m.11:30 a.m.
Stars & Garters Theater
3914 N. Clark St.
The Infinite Wrench
Oct17
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, October 17th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Ben Schwartz & Friends
Oct17
Music & Comedy

Ben Schwartz & Friends

Ben Schwartz is bringing his “Ben Schwartz & Friends” tour to Chicago for a night of unscripted improv comedy in the fall of 2026.

Saturday, October 17th
7:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Baby Wants Candy! The Original Completely Improvised Musical
Oct17
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, October 17th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Oct17
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, October 17th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Secret Sketch Show
Oct17
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, October 17th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Oct17
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, October 17th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Magic Mondays
Oct19
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, October 19th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Disney Descendants & Zombies: Worlds Collide
Oct19
Music & Comedy

Disney Descendants & Zombies: Worlds Collide

The all-new “Worlds Collide Concert Tour” brings together the worlds of “Descendants,” “ZOMBIES,” and for the very first time, “Camp Rock,”in an unforgettable new arena spectacular. A pop concert…

Monday, October 19th
7:00 p.m.10:00 p.m.
United Center
1901 W Madison St,
Tuesday Good Show
Oct20
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, October 20th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Disney Descendants & Zombies: Worlds Collide
Oct21
Music & Comedy

Disney Descendants & Zombies: Worlds Collide

The all-new “Worlds Collide Concert Tour” brings together the worlds of “Descendants,” “ZOMBIES,” and for the very first time, “Camp Rock,”in an unforgettable new arena spectacular. A pop concert…

Wednesday, October 21st
7:00 p.m.10:00 p.m.
Allstate Arena
6920 Mannheim Road