ComedySportz Chicago
Jan17
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Saturday, January 17th
6:00 p.m.7:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Infinite Wrench
Jan17
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, January 17th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Brady Matthews at The Comedy Bar
Jan17
Music & Comedy

Brady Matthews at The Comedy Bar

Brady Matthews is a comedic powerhouse with charisma to spare. He’s opened for legends like Demetri Martin and Trevor Wallace, headlined at top festivals including…

Saturday, January 17th
7:00 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Teatro Zinzanni
Jan17
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…

Saturday, January 17th
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Baby Wants Candy! The Original Completely Improvised Musical
Jan17
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, January 17th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Jan17
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, January 17th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Improvised Jane Austen
Jan17
Music & Comedy, Theatre & Performing Arts

Improvised Jane Austen

Celebrate Jane Austen’s birthday all winter long with Improvised Jane Austen! Just one day cannot encapsulate a proper observation of Jane Austen’s life and work.…

Saturday, January 17th
7:30 p.m.8:30 p.m.
iO Chicago
1501 N Kingsbury St,
Evan Plus One: Party Animals
Jan17
Music & Comedy

Evan Plus One: Party Animals

Evan Plus One: Party AnimalsWinners of Season 38 of The Original Improv Gladiators Get ready for a night of improv worthy of a celebration! Evan…

Saturday, January 17th
7:30 p.m.8:30 p.m.
Cornservatory
4210 N Lincoln Ave
New Year New Show
Jan17
Music & Comedy, Theatre & Performing Arts

New Year New Show

New Year! New Show! Welcome to 2026 where the laughter runs hot and the jokes run cheap. Every week is a brand new sketch show,…

Saturday, January 17th
8:00 p.m.9:00 p.m.
The De Matt Theater at The Second City
230 W North Ave
ComedySportz Chicago
Jan17
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Saturday, January 17th
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Cosmic Underground Show
Jan17
Music & Comedy, Theatre & Performing Arts

The Cosmic Underground Show

The Cosmic Underground Show blasts off for a 90-minute immersive comedy, magic, and mind-reading show. Cosmic founders Harrison Lampert (a quirky sleight-of-hand expert) and Kayla…

Saturday, January 17th
8:00 p.m.9:30 p.m.
cosmic underground theater
3433 W Fullerton Ave
Brian Regan Live!
Jan17
Music & Comedy

Brian Regan Live!

Acclaimed comedian Brian Regan is scheduled to perform in Chicago on Saturday, January 17, 2026, at The Chicago Theatre.

Saturday, January 17th
8:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Secret Sketch Show
Jan17
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, January 17th
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Brady Matthews at The Comedy Bar
Jan17
Music & Comedy

Brady Matthews at The Comedy Bar

Brady Matthews is a comedic powerhouse with charisma to spare. He’s opened for legends like Demetri Martin and Trevor Wallace, headlined at top festivals including…

Saturday, January 17th
9:00 p.m.11:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Best Of Annoyance Sketch
Jan17
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, January 17th
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Julia Bullock and Seth Parker Woods with Conor Hanick
Jan18
Music & Comedy

Julia Bullock and Seth Parker Woods with Conor Hanick

Two-time GRAMMY-nominated cellist Seth Parker Woods propels classical music into the future through projects that delve deep into our cultural fabric. GRAMMY-winning American classical singer…

Sunday, January 18th
3:00 p.m.4:30 p.m.
Reva and David – Logan Center for the Arts
915 E 60th St
Teatro Zinzanni
Jan18
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…

Sunday, January 18th
4:00 p.m.7:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Almost 24 Hours: A Sketch Show
Jan18
Music & Comedy

Almost 24 Hours: A Sketch Show

Time for a brand new Almost 24 Hours show coming at ya! As always, 8 writers will be given the night to write their sketch,…

Sunday, January 18th
7:00 p.m.8:30 p.m.
Cornservatory
4210 N Lincoln Ave
Guerrilla Press feat. Kat Abughazaleh & Malort And Savior
Jan18
Music & Comedy

Guerrilla Press feat. Kat Abughazaleh & Malort And Savior

Guerrilla Press is The Annoyance Theater’s first-ever live, weekly podcast! Every Sunday night, comedians EJ Cameron and Nick Hausman give their no-holds-barred comedic take on…

Sunday, January 18th
7:00 p.m.9:00 p.m.
Annoyance Theatre and Bar
851 West Belmont Avenue
Zako Ryan at The Comedy Bar
Jan18
Music & Comedy

Zako Ryan at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Zako Ryan grew up in the…

Sunday, January 18th
7:00 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
Teatro Zinzanni
Jan18
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale now at https://zinzanni.com/chicago/tickets/ “Best Night Out” – CS Magazine | “You must see to believe!” – Forbes Teatro ZinZanni, Chicago’s most…

Sunday, January 18th
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Wheel of Improv
Jan18
Music & Comedy, Theatre & Performing Arts

Wheel of Improv

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…

Sunday, January 18th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
That 90s Throwback Comedy Show
Jan18
Music & Comedy, Theatre & Performing Arts

That 90s Throwback Comedy Show

Calling all 90s kids! This show is for you. Each month, Chicago’s hottest comedians share their favorite 90s obsessions while the audience battles over trivia…

Sunday, January 18th
8:00 p.m.9:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Magic Mondays
Jan19
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, January 19th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.