Hitch*Cocktails
Dec18
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, December 18th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Stargazers Adventure Club
Dec19
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, December 19th
10:00 a.m.11:30 a.m.
Stars & Garters Theater
3914 N. Clark St.
The Infinite Wrench
Dec19
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, December 19th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Home Alone 2: Lost In New York – Film With Live Orchestra
Dec19
Music & Comedy

Home Alone 2: Lost In New York – Film With Live Orchestra

Experience Home Alone 2: Lost in New York – Live in Concert as Award-winning composer John Williams’ score is performed live to film by the Chicago Philharmonic! The score for Home Alone 2 Lost in New York is an…

Saturday, December 19th
7:00 p.m.9:00 p.m.
Auditorium
50 East Ida B. Wells Drive
Baby Wants Candy! The Original Completely Improvised Musical
Dec19
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, December 19th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Dec19
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, December 19th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Secret Sketch Show
Dec19
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, December 19th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Dec19
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, December 19th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Magic Mondays
Dec21
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, December 21st
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Tuesday Good Show
Dec22
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 22nd
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Comic Court: Chicago’s #1 Comedy Court Show
Dec22
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Comic Court: Chicago’s #1 Comedy Court Show

Order in the court!Comic Court is back at The Lincoln Lodge every 2nd & 4th Tuesday at 9PM. Comedians argue ridiculous cases like actual lawyers,…

Tuesday, December 22nd
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
The Orbit
Dec23
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 23rd
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Hooch & Holler Comedy Show
Dec23
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, December 23rd
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
Dec23
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, December 23rd
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
DuSummer Live Music Series
Dec24
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, December 24th
6:00 p.m.9:00 p.m.
Dusable Black History Museum and Cultural Centwe
740 East 57th Place
Morgan’s Laugh Lounge
Dec24
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, December 24th
7:00 p.m.8:30 p.m.
Morgan’s On Fulton
950 W Fulton Market
The Infinite Wrench
Dec25
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, December 25th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
The Last Word
Dec25
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, December 25th
7:00 p.m.9:30 p.m.
iO Theater
1501 N. Kingsbury St.
Devil’s Daughter
Dec25
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, December 25th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Devil’s Daughter
Dec25
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, December 25th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Honk! A Short Form Improv Show
Dec25
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, December 25th
9:00 p.m.10:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Voila: The Improvised Musical
Dec25
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, December 25th
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
Dec25
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, December 25th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Stargazers Adventure Club
Dec26
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, December 26th
10:00 a.m.11:30 a.m.
Stars & Garters Theater
3914 N. Clark St.