Trapped in a Musical – an improvised musical
Feb13
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 13th
9:00 p.m.10:00 p.m.
Prov Ur Love 2 Me
Feb13
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 13th
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St.
Calvin Evans at The Comedy Bar
Feb13
Music & Comedy

Calvin Evans at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Chicago native Calvin Evans’ comedy career…

Friday, February 13th
9:00 p.m.10:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Voila: The Improvised Musical
Feb13
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 13th
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
Feb13
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 13th
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
Feb14
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 14th
Fine Arts Building | Studebaker Theater
410 South Michigan Avenue
“Clue” presented by The Beverly Theatre Guild
Feb14
Music & Comedy, Theatre & Performing Arts

“Clue” presented by The Beverly Theatre Guild

Chicago, IL: The Beverly Theatre Guild (BTG) is thrilled to present the iconic comedy Clue on February 13-15, 2026. In this fun murder-mystery, based on…

Saturday, February 14th
2:00 p.m.3:30 p.m.
Baer Theater at Morgan Park Academy
2153 W 111th St, Chicago, IL, 60643
The Cosmic Underground Show-Valentine’s Day Matinee
Feb14
Music & Comedy, Theatre & Performing Arts

The Cosmic Underground Show-Valentine’s Day Matinee

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

Saturday, February 14th
4:30 p.m.6:00 p.m.
cosmic underground theater
3433 W Fullerton Ave
Josh Johnson Live!
Feb14
Music & Comedy

Josh Johnson Live!

Comedian Josh Johnson will perform live at The Chicago Theatre on Feb. 14-15, 2026.

Saturday, February 14th
5:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
ComedySportz Chicago
Feb14
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 14th
6:00 p.m.7:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Infinite Wrench
Feb14
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 14th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Calvin Evans at The Comedy Bar
Feb14
Music & Comedy

Calvin Evans at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Chicago native Calvin Evans’ comedy career…

Saturday, February 14th
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Valen-Wine’s Day: A Comedy & Wine Pairing
Feb14
Music & Comedy

Valen-Wine’s Day: A Comedy & Wine Pairing

This Valentine’s Day, fall in love one glass at a time. Valen-Wine’s Day pairs six of Chicago’s best stand-up comedians with six different wines, creating…

Saturday, February 14th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Teatro Zinzanni
Feb14
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 14th
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Heartbeat House Party at Shedd Aquarium
Feb14
Museums, Galleries & Exhibitions, Music & Comedy

Heartbeat House Party at Shedd Aquarium

Feel the love and the rhythm at the first-ever Heartbeat House Party! Celebrate Valentine’s Day beneath the waves with house music and aquatic allure. Dress…

Saturday, February 14th
7:00 p.m.11:00 p.m.
Shedd Aquarium
1200 S. Lake Shore Dr.
Baby Wants Candy! The Original Completely Improvised Musical
Feb14
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 14th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
Feb14
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 14th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Improvised Jane Austen
Feb14
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 14th
7:30 p.m.8:30 p.m.
iO Chicago
1501 N Kingsbury St,
The Original Improv Gladiators: Season 39
Feb14
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 14th
7:30 p.m.9:00 p.m.
Cornservatory
4210 N Lincoln Ave
Salome
Feb14
Music & Comedy, Theatre & Performing Arts

Salome

Based on Oscar Wilde’s one-act play, Salome has been thrilling and fascinating audiences for more than a century. Lyric Opera of Chicago brings Sir David McVicar’s decadent…

Saturday, February 14th
7:30 p.m.9:15 p.m.
Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606
The Kitty & Kellie Show
Feb14
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 14th
8:00 p.m.9:00 p.m.
The De Matt Theater at The Second City
230 W North Ave
ComedySportz Chicago
Feb14
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 14th
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Cosmic Underground Show
Feb14
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 14th
8:00 p.m.9:30 p.m.
cosmic underground theater
3433 W Fullerton Ave
Calvin Evans at The Comedy Bar
Feb14
Music & Comedy

Calvin Evans at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Chicago native Calvin Evans’ comedy career…

Saturday, February 14th
9:00 p.m.10:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611