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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 14th
9:00 p.m. – 10:30 p.m.iO Theater
1501 N. Kingsbury St.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 14th
9:30 p.m. – 10:30 p.m.The Annoyance Theatre
851 W. Belmont Ave.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…
Sunday, February 15th
2:00 p.m. – 3:30 p.m.Baer Theater at Morgan Park Academy
2153 W 111th St, Chicago, IL, 60643Music & Comedy
Lynne Davis, concert organist
Lynne Davis brings the grandeur of French organ music to life with a mastery honed over decades of study, performance, and teaching. Launched into international…
Sunday, February 15th
3:00 p.m. – 4:30 p.m.Bond Chapel, University of Chicago
1025 E. 58th 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…
Sunday, February 15th
4:00 p.m. – 7:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphMusic & Comedy
Josh Johnson Live!
Comedian Josh Johnson will perform live at The Chicago Theatre on Feb. 14-15, 2026.
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 15th
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 15th
6:00 p.m. – 7:00 p.m.The De Matt Theater at The Second City
230 W North AveMusic & 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…
Sunday, February 15th
7:00 p.m. – 10:00 p.m.Teatro ZinZanni – Cambria Hotel
32 W Randolph StMusic & 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, Theatre & Performing Arts
Magic Mondays
Experience an unforgettable night of wonder at Magic Mondays!! Starring award-winning magician John Sturk, this monthly showcase features Chicago’s top conjurors performing mind-blowing illusions and…
Music & 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 17th
7:00 p.m. – 8:30 p.m.The Gallery Cabaret
2020 N Oakley AveMusic & Comedy
Freya Skye – Stars Align 2026 Tour
Pop singer Freya Skye will perform live at Chicago’s The Salt Shed Indoors on Feb. 18, 2026.
Wednesday, February 18th
8:00 p.m. – 11:00 p.m.The Salt Shed
1357 N Elston Ave, Chicago, ILMusic & Comedy
Monolink – The Beauty of It All Tour
German singer-songwriter and electronic dance music producer Monolink is scheduled to perform in Chicago on Wednesday, February 18, 2026, as part of “The Beauty of…
Wednesday, February 18th
8:00 p.m. – 11:00 p.m.The Vic Theatre
3145 N. SheffieldMusic & 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 18th
9:00 p.m. – 11:00 p.m.Bordel Cocktail & Cabaret
1721 W DivisionMusic & 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…
Thursday, February 19th
7:00 p.m. – 10:00 p.m.Teatro ZinZanni – Cambria Hotel
32 W Randolph StFestivals, 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 19th
7:30 p.m. – 8:30 p.m.The Second City
1616 N. Wells St.Music & Comedy, Theatre & Performing Arts
Dumb and Drummer
Chicago’s best comedians doing their best material over live jazz! Every third Thursday at The Lincoln Lodge Theatre, Hosted by Jamaal Sanders, Hunter Hirsch, and…
Thursday, February 19th
7:30 p.m. – 9:00 p.m.The Lincoln Lodge Theater
2040 N. Milwaukee Ave.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 19th
8:00 p.m. – 9:00 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy
Class! with Chad the Bird and Sara Benincasa
Your professors Sara Benincasa and Chad the Bird present a night of mildly educated comedy on a stimulating subject w/ their favorite comedians! No degree?…
Thursday, February 19th
8:00 p.m. – 9:30 p.m.The Lincoln Lodge
2040 North Milwaukee AvenueMusic & 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 19th
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 19th
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 20thFine Arts Building | Studebaker Theater
410 South Michigan AvenueMusic & 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 20th
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.

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