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
Hooch & Holler Comedy Show
Oct21
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 21st
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
Oct21
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 21st
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
Morgan’s Laugh Lounge
Oct22
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 22nd
7:00 p.m.8:30 p.m.
Morgan’s On Fulton
950 W Fulton Market
The Buena Vista Orchestra
Oct22
Music & Comedy

The Buena Vista Orchestra

The Buena Vista Orchestra is scheduled to perform in Chicago, IL, on Thursday, October 22, 2026.

Thursday, October 22nd
7:30 p.m.10:30 p.m.
The Vic Theatre
3145 N. Sheffield
The Infinite Wrench
Oct23
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 23rd
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Randy Feltface – Gimmick Tour
Oct23
Music & Comedy

Randy Feltface – Gimmick Tour

Australian comedian Randy Feltface is scheduled to perform in Chicago on Friday, October 23, 2026, as part of his “Gimmick” tour.

Friday, October 23rd
7:00 p.m.9:00 p.m.
The Vic Theatre
3145 N. Sheffield
Devil’s Daughter
Oct23
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 23rd
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Tedeschi Trucks Band – Future Soul 2026 Tour
Oct23
Music & Comedy

Tedeschi Trucks Band – Future Soul 2026 Tour

Award-winning blues-rock powerhouse The Tedeschi Trucks Band will conclude their “Future Soul 2026 Tour” with a four-night stand in Chicago in October 2026.

Friday, October 23rd
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
Devil’s Daughter
Oct23
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 23rd
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Sammy Rae & The Friends – The Album Tour
Oct23
Music & Comedy

Sammy Rae & The Friends – The Album Tour

Sammy Rae & The Friends are scheduled to perform in Chicago on Friday, October 23, 2026, as part of “The Album Tour”. Special Guest: The…

Friday, October 23rd
8:00 p.m.11:00 p.m.
The Salt Shed
1357 N Elston Ave, Chicago, IL
Honk! A Short Form Improv Show
Oct23
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 23rd
9:00 p.m.10:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Voila: The Improvised Musical
Oct23
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 23rd
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
Oct23
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 23rd
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Stargazers Adventure Club
Oct24
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 24th
10:00 a.m.11:30 a.m.
Stars & Garters Theater
3914 N. Clark St.
The Infinite Wrench
Oct24
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 24th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Baby Wants Candy! The Original Completely Improvised Musical
Oct24
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 24th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Oct24
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 24th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Tedeschi Trucks Band – Future Soul 2026 Tour
Oct24
Music & Comedy

Tedeschi Trucks Band – Future Soul 2026 Tour

Award-winning blues-rock powerhouse The Tedeschi Trucks Band will conclude their “Future Soul 2026 Tour” with a four-night stand in Chicago in October 2026.

Saturday, October 24th
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
Secret Sketch Show
Oct24
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 24th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Oct24
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 24th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.