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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 8th
6:00 p.m. – 7:00 p.m.The De Matt Theater at The Second City
230 W North AveMusic & 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 8th
6:00 p.m. – 7:00 p.m.The De Matt Theater at The Second City
230 W North AveMusic & Comedy, Theatre & Performing Arts
Wheel of Improv
Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!)…
Music & Comedy
Pitch and Pair: Pitch your friend to a crowd of singles (Valentines Edition)
Pitch & Pair at The Comedy Bar Friends pitch their single besties with a 3–5 minute slide deck to a room full of singles. Watch,…
Monday, February 9th
6:30 p.m. – 9:00 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy, Theatre & Performing Arts
Pitch and Pair: Pitch your friend to a crowd of singles (Valentines Edition)
Pitch & Pair at The Comedy Bar Friends pitch their single besties with a 3–5 minute slide deck to a room full of singles. Watch,…
Monday, February 9th
6:30 p.m. – 9:00 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy
Pitch & Pair at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Tired of endless swiping, awkward first…
Monday, February 9th
7:30 p.m. – 9:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy
Tuesday Good Show
Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…
Tuesday, February 10th
7:00 p.m. – 8:30 p.m.The Gallery Cabaret
2020 N Oakley AveMusic & Comedy
The Runarounds
Welcome to the iconic Metro Chicago in the heart of the Windy City! Get ready to experience the electrifying performance by The Runarounds on February…
Tuesday, February 10th
7:00 p.m. – 9:00 p.m.Metro ChicagoMusic & Comedy
Tomato Throw Show at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Join us for the most fun…
Tuesday, February 10th
7:00 p.m. – 9:00 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy, Theatre & Performing Arts
Così fan tutte
Two officers, convinced all women are fickle in love, hatch a plan to switch places and woo each other’s fiancées in disguise — but the…
Tuesday, February 10th
7:00 p.m. – 10:30 p.m.Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
SO THIS SUCKS: The Annual Anti Valentine’s Day Show From About Last Night
For the first time ever, the creators of About Last Night – San Francisco’s favorite one night stand storytelling series – are bringing their annual…
Tuesday, February 10th
8:00 p.m. – 10:00 p.m.The Den Theatre
1331 North Milwaukee AvenueFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Comic Court: Chicago’s #1 Comedy Court Show
Order in the court!Comic Court is back at The Lincoln Lodge every 2nd & 4th Tuesday at 9PM. Comedians argue ridiculous cases like actual lawyers,…
Tuesday, February 10th
9:00 p.m. – 10:30 p.m.The Lincoln Lodge
2040 North Milwaukee AvenueMusic & Comedy
Crowd Work Wednesday at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Crowd Work Wednesday is a weekly…
Wednesday, February 11th
7:00 p.m. – 9:00 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy, Theatre & Performing Arts
SECRETS starring mentalist SIDNEY FRIEDMAN
Perfect for Valentine’s week, star TV mentalist SIDNEY FRIEDMAN returns to The Alley inside CARNIVALE for his interactive, elevating, award-winning performance of mind reading. As…
Wednesday, February 11th
7:30 p.m. – 9:00 p.m.Carnivale
702 w fulton marketMusic & Comedy
Opeth – The Last Will And Testament 2026 Tour
Swedish progressive metal icons Opeth/w special guests Katatonia will perform live at Riviera Theatre on Feb. 11, 2026.
Wednesday, February 11th
7:30 p.m. – 10:30 p.m.The Riveria Theater
4746 N Racine AveMusic & Comedy, Theatre & Performing Arts
Hooch & Holler Comedy Show
Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…
Wednesday, February 11th
9:00 p.m. – 11:00 p.m.Bordel Cocktail & Cabaret
1721 W DivisionFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Improvised Sketch Show
Improvised Sketch Show is a weekly sketch show written in real time by a rotating cast of improvisers alongside YOU, the audience. It’s the structure…
Thursday, February 12th
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St.Music & Comedy, Theatre & Performing Arts
Improvsed DCOM
Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM! This All Star cast is bringing screen to stage every…
Thursday, February 12th
8:00 p.m. – 9:00 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy, Theatre & Performing Arts
Love is Improvised
An improvised take on a hit reality-TV show that dares to ask… is love truly improvised? A cast of 10 improvisers embark on a journey…
Thursday, February 12th
8:30 p.m. – 9:30 p.m.Judy’s Beat Lounge
230 W. North Ave. 2nd FloorFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Sketch Playlist
Sketch Playlist is a weekly sketch show that will feature all-new sketches every single week… the ultimate sketch playlist. Come see these writers and performers…
Thursday, February 12th
9:30 p.m. – 10:30 p.m.iO Theater
1501 N. Kingsbury St.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…
Friday, February 13thFine Arts Building | Studebaker Theater
410 South Michigan AvenueFestivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
The Dance Center and BraveSoul Movement present B-SERIES 2026: B-PRESENT BATTLE & JAM
The 12th annual celebration of Hip Hop & Street Dance Culture co-curated by faculty Daniel BRAVEMONK Haywood and Kelsa K-SOUL Rieger-Haywood. This year’s theme B-PRESENT…
Friday, February 13th
11:00 a.m. – 12:30 p.m.Columbia College Chicago Dance Center
1306 South Michigan AvenueMusic & Comedy, Theatre & Performing Arts
Così fan tutte
Two officers, convinced all women are fickle in love, hatch a plan to switch places and woo each other’s fiancées in disguise — but the…
Friday, February 13th
2:00 p.m. – 5:30 p.m.Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606Music & 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…
Friday, February 13th
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.

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