The Orbit
Nov25
Music & Comedy, Theatre & Performing Arts

The Orbit

The Orbit is Chicago’s only improv show performed in the round. This 45-minute avant-garde experience takes the audience on a full-circle journey, showcasing a bold…

Wednesday, November 25th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Hooch & Holler Comedy Show
Nov25
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, November 25th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
Nov25
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, November 25th
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
DuSummer Live Music Series
Nov26
Music & Comedy

DuSummer Live Music Series

DuSummer Music Series 2026  Get ready for an unforgettable summer of music at the DuSable Museum Outdoor Courtyard! Join us every other Thursday for some…

Thursday, November 26th
6:00 p.m.9:00 p.m.
Dusable Black History Museum and Cultural Centwe
740 East 57th Place
Morgan’s Laugh Lounge
Nov26
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, November 26th
7:00 p.m.8:30 p.m.
Morgan’s On Fulton
950 W Fulton Market
The Infinite Wrench
Nov27
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, November 27th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
The Last Word
Nov27
Music & Comedy, Theatre & Performing Arts

The Last Word

The Last Word is the first 4 course craft cocktail progression paired with a screenplay. 6 actors come on stage and read through a high…

Friday, November 27th
7:00 p.m.9:30 p.m.
iO Theater
1501 N. Kingsbury St.
The Pineapple Thief – Far and Wide Tour
Nov27
Music & Comedy

The Pineapple Thief – Far and Wide Tour

The Pineapple Thief is performing at the House of Blues Chicago on Friday, November 27, 2026, as part of their “Far and Wide Tour.” Special…

Friday, November 27th
7:00 p.m.10:00 p.m.
Devil’s Daughter
Nov27
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, November 27th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Devil’s Daughter
Nov27
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, November 27th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
A Drag Queen Christmas
Nov27
Music & Comedy

A Drag Queen Christmas

Murray & Peter Present A Drag Queen Christmas hosted by Nina West. It’s the longest running drag tour in America. Get ready for your favorite…

Friday, November 27th
8:00 p.m.10:00 p.m.
The Riveria Theater
4746 N Racine Ave
Honk! A Short Form Improv Show
Nov27
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, November 27th
9:00 p.m.10:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Voila: The Improvised Musical
Nov27
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, November 27th
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
Nov27
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, November 27th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Stargazers Adventure Club
Nov28
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, November 28th
10:00 a.m.11:30 a.m.
Stars & Garters Theater
3914 N. Clark St.
Whitechapel – 20th Anniversary Tour
Nov28
Music & Comedy

Whitechapel – 20th Anniversary Tour

Whitechapel is performing live in Chicago on Saturday, November 28, 2026, at The Riviera Theatre as part of their massive 20th Anniversary Tour. Lineup: Whitechapel,…

Saturday, November 28th
5:45 p.m.11:00 p.m.
The Riveria Theater
4746 N Racine Ave
The Infinite Wrench
Nov28
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, November 28th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Baby Wants Candy! The Original Completely Improvised Musical
Nov28
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, November 28th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Nov28
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, November 28th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Dexter and The Moonrocks: 2026 Tour
Nov28
Music & Comedy

Dexter and The Moonrocks: 2026 Tour

Rising “Western Space Grunge” pioneers Dexter and The Moonrocks will perform live in Chicago on Saturday, November 28, 2026, at 8:00 PM at the historic…

Saturday, November 28th
8:00 p.m.11:00 p.m.
Secret Sketch Show
Nov28
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, November 28th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Nov28
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, November 28th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Tuesday Good Show
Dec1
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, December 1st
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
The Orbit
Dec2
Music & Comedy, Theatre & Performing Arts

The Orbit

The Orbit is Chicago’s only improv show performed in the round. This 45-minute avant-garde experience takes the audience on a full-circle journey, showcasing a bold…

Wednesday, December 2nd
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.