ComedySportz Chicago
Feb20
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 20th
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
ComedySportz Chicago
Feb20
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 20th
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Rules of Bad Behavior – A Sketch Comedy Show
Feb20
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 20th
7:00 p.m.8:30 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Teatro Zinzanni
Feb20
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 20th
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Brandi Carlile Live at Allstate Arena – The Human 2026 Tour
Feb20
Music & Comedy

Brandi Carlile Live at Allstate Arena – The Human 2026 Tour

Acclaimed singer-songwriter Brandi Carlile brings The Human 2026 Tour to Allstate Arena in Rosemont on February 20, offering a night of emotionally charged performances and…

Friday, February 20th
7:00 p.m.10:00 p.m.
Allstate Arena
6920 Mannheim Road
Devil’s Daughter
Feb20
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 20th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
The Original Improv Gladiators: Season 39
Feb20
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 20th
7:30 p.m.9:00 p.m.
Cornservatory
4210 N Lincoln Ave
Rich Brian – Where Is My Head? 2026 World Tour
Feb20
Music & Comedy

Rich Brian – Where Is My Head? 2026 World Tour

Indonesian rapper and Vine sensation Rich Brian is scheduled to perform in Chicago on Friday, February 20, 2026, as part of his “Where Is My…

Friday, February 20th
7:30 p.m.10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Devil’s Daughter
Feb20
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 20th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
Feb20
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 20th
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
The Cosmic Underground Show
Feb20
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 20th
8:00 p.m.9:30 p.m.
cosmic underground theater
3433 W Fullerton Ave
Justin Bieber Night
Feb20
Music & Comedy

Justin Bieber Night

Justin Bieber Night: Presented by Stan Society is a dance party event scheduled to take place in Chicago. Please note that this is a themed…

Friday, February 20th
8:30 p.m.11:30 p.m.
Trapped in a Musical – an improvised musical
Feb20
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 20th
9:00 p.m.10:00 p.m.
Prov Ur Love 2 Me
Feb20
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 20th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St.
Voila: The Improvised Musical
Feb20
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 20th
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
Feb20
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 20th
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Roald Dahl’s The Enormous Crocodile: The Musical
Feb21
Music & Comedy, Theatre & Performing Arts

Roald Dahl’s The Enormous Crocodile: The Musical

The Enormous Crocodile musical brings Roald Dahl’s story to life with puppets, music, and laughs — a fun family show at Chicago’s Studebaker Theater. “For…

Saturday, February 21st
Fine Arts Building | Studebaker Theater
410 South Michigan Avenue
Tikka Masala
Feb21
Music & Comedy, Theatre & Performing Arts

Tikka Masala

Tikka Masala is an Indian Improv Comedy Game Show. Get ready for a laugh-out-loud night of unscripted chaos, cultural flavor, and spicy twists! Tikka Masala…

Saturday, February 21st
6:00 p.m.7:00 p.m.
iO Theater
1501 N. Kingsbury St.
ComedySportz Chicago
Feb21
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 21st
6:00 p.m.7:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Infinite Wrench
Feb21
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 21st
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Alfred Robles Live!
Feb21
Music & Comedy

Alfred Robles Live!

Comedian Alfred Robles is scheduled to perform in Chicago, IL, on Saturday, February 21, 2026.

Saturday, February 21st
7:00 p.m.9:00 p.m.
The Vic Theatre
3145 N. Sheffield
Teatro Zinzanni
Feb21
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 21st
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Baby Wants Candy! The Original Completely Improvised Musical
Feb21
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 21st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Feb21
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 21st
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor