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.
Ahmed Ahmed at The Comedy Bar
Feb20
Music & Comedy

Ahmed Ahmed at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Egyptian-American actor, comedian, producer, and director…

Friday, February 20th
9:00 p.m.10:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
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.
Ahmed Ahmed at The Comedy Bar
Feb21
Music & Comedy

Ahmed Ahmed at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Egyptian-American actor, comedian, producer, and director…

Saturday, February 21st
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
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
My Sweet George: George Harrison Birthday Tribute
Feb21
Music & Comedy

My Sweet George: George Harrison Birthday Tribute

7:15 PM – James Bourland (Acoustic Duet, with special guest Frankie B) 7:35 PM – Pierce Crask (Solo Acoustic Set) 7:55 PM – Clar &…

Saturday, February 21st
7:00 p.m.11:30 p.m.
Martyrs’
3855 North Lincoln Avenue
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
Improvised Jane Austen
Feb21
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 21st
7:30 p.m.8:30 p.m.
iO Chicago
1501 N Kingsbury St,
The Original Improv Gladiators: Season 39
Feb21
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…

Saturday, February 21st
7:30 p.m.9:00 p.m.
Cornservatory
4210 N Lincoln Ave
The Kitty & Kellie Show
Feb21
Music & Comedy, Theatre & Performing Arts

The Kitty & Kellie Show

Get your gals pals, your pal gals, and your gals ready as Kellie and Kitty take the stage for this Galentines-themed event. This goes beyond…

Saturday, February 21st
8:00 p.m.9:00 p.m.
The De Matt Theater at The Second City
230 W North Ave
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
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Cosmic Underground Show
Feb21
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, February 21st
8:00 p.m.9:30 p.m.
cosmic underground theater
3433 W Fullerton Ave
Secret Sketch Show
Feb21
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, February 21st
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Ahmed Ahmed at The Comedy Bar
Feb21
Music & Comedy

Ahmed Ahmed at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Egyptian-American actor, comedian, producer, and director…

Saturday, February 21st
9:00 p.m.10:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Best Of Annoyance Sketch
Feb21
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, February 21st
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Crashed Course History
Feb22
Music & Comedy, Theatre & Performing Arts

Crashed Course History

Forget what you learned in school. This is history for weirdos and degenerates. Crashed Course History is an absurdist sketch comedy revue with music, costumes,…

Sunday, February 22nd
6:00 p.m.7:00 p.m.
The De Matt Theater at The Second City
230 W North Ave