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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.Malarkey Comedy, Home of ComedySportz Chicago
929 W. Belmont Ave.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…
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 60611Music & 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,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.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 14thFine Arts Building | Studebaker Theater
410 South Michigan AvenueMusic & 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, 60643Music & 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 AveMusic & 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. StateMusic & 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 StMusic & 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.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 60611Music & 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.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 StMuseums, 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.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.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 FloorMusic & 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.…
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…
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, 60606Music & 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 AveMusic & 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 StMusic & 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 AveMusic & 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

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