ComedySportz Chicago
Feb27
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…

Friday, February 27th
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Rules of Bad Behavior – A Sketch Comedy Show
Feb27
Music & Comedy

The Rules of Bad Behavior – A Sketch Comedy Show

The Rules of Bad Behavior get recklessly applied to everything in this all-new, all-original sketch comedy revue! From awkward run-ins with Keanu Reeves at the…

Friday, February 27th
7:00 p.m.8:30 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Teatro Zinzanni
Feb27
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…

Friday, February 27th
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Devil’s Daughter
Feb27
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, February 27th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
The Original Improv Gladiators: Season 39
Feb27
Music & Comedy

The Original Improv Gladiators: Season 39

What started as an idea to fill a recently vacated production slot back in January of 2008 has turned into a sure-fire hit improv-aganza and…

Friday, February 27th
7:30 p.m.9:00 p.m.
Cornservatory
4210 N Lincoln Ave
Matteo Mancuso – Route 96 Tour
Feb27
Music & Comedy

Matteo Mancuso – Route 96 Tour

Italian guitarist Matteo Mancuso is scheduled to perform in Chicago on Feb. 27, 2026 as part of his North American “Route 96 Tour”.

Friday, February 27th
7:30 p.m.10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Cat Power – The Greatest Tour
Feb27
Music & Comedy

Cat Power – The Greatest Tour

Singer-songwriter Cat Power is scheduled to perform in Chicago on Friday, February 27, 2026, as part of her “The Greatest Tour”. This headlining run celebrates…

Friday, February 27th
7:30 p.m.10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Devil’s Daughter
Feb27
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, February 27th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
Feb27
Music & Comedy, Theatre & Performing Arts

Missed Call Sketch Comedy Show

Missed Call is a premier Chicago comedy group that writes and performs an entirely new sketch show every Friday — inspired by the audience’s suggestion!

Friday, February 27th
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The Cosmic Underground Show
Feb27
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…

Friday, February 27th
8:00 p.m.9:30 p.m.
cosmic underground theater
3433 W Fullerton Ave
Vir Das – Hey Stranger: A Tour of the World
Feb27
Music & Comedy

Vir Das – Hey Stranger: A Tour of the World

Indian comedian and actor Vir Das will perform in Chicago on Friday, February 27, 2026, at The Chicago Theatre. This show is part of his…

Friday, February 27th
8:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Trapped in a Musical – an improvised musical
Feb27
Music & Comedy, Theatre & Performing Arts

Trapped in a Musical – an improvised musical

Trapped in a Musical is a completely improvised Broadway-style show created before your very eyes. It’s the opening and closing night of a brand new…

Friday, February 27th
9:00 p.m.10:00 p.m.
Prov Ur Love 2 Me
Feb27
Music & Comedy, Theatre & Performing Arts

Prov Ur Love 2 Me

Step into the villa for Prov Ur Love 2 Me – Season 3. After a hot and spicy season one and two, a whole new…

Friday, February 27th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St.
Voila: The Improvised Musical
Feb27
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, February 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
Feb27
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, February 27th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
ComedySportz Chicago
Feb28
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, February 28th
6:00 p.m.7:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Nothing More – Carnal Nature 2026 World Tour
Feb28
Music & Comedy

Nothing More – Carnal Nature 2026 World Tour

Triple-Grammy-nominated outfit Nothing More/w special guests Catch Your Breath, Archers & Doobie will perform live at Riviera Theatre on Feb. 28, 2026.

Saturday, February 28th
6:30 p.m.10:00 p.m.
The Riveria Theater
4746 N Racine Ave
The Infinite Wrench
Feb28
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, February 28th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Sherri Shepherd
Feb28
Music & Comedy

Sherri Shepherd

Welcome to the Vic Theatre in Chicago, Illinois, where the talented Sherri Shepherd will be gracing the stage on February 28, 2026, at 7:00 PM.…

Saturday, February 28th
7:00 p.m.9:00 p.m.
The Vic Theatre
3145 N. Sheffield
René Vaca Live!
Feb28
Music & Comedy

René Vaca Live!

Rising comedian, René Vaca is scheduled to perform at The Chicago Theatre on Saturday, February 28, 2026.

Saturday, February 28th
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
Teatro Zinzanni
Feb28
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, February 28th
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Baby Wants Candy! The Original Completely Improvised Musical
Feb28
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, February 28th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Feb28
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, February 28th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Improvised Jane Austen
Feb28
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, February 28th
7:30 p.m.8:30 p.m.
iO Chicago
1501 N Kingsbury St,