Secret Sketch Show
Feb14
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.
Best Of Annoyance Sketch
Feb14
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.
“Clue” presented by The Beverly Theatre Guild
Feb15
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, 60643
Lynne Davis, concert organist
Feb15
Music & 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.
Teatro Zinzanni
Feb15
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. Randolph
Josh Johnson Live!
Feb15
Music & Comedy

Josh Johnson Live!

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

Sunday, February 15th
5:00 p.m.10:00 p.m.
The Chicago Theatre
175 N. State
Crashed Course History
Feb15
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 Ave
Crashed Course History
Feb15
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 Ave
Teatro Zinzanni
Feb15
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
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Wheel of Improv
Feb15
Music & 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!)…

Sunday, February 15th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Magic Mondays
Feb16
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…

Monday, February 16th
7:00 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Tuesday Good Show
Feb17
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 Ave
Freya Skye – Stars Align 2026 Tour
Feb18
Music & 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, IL
Monolink – The Beauty of It All Tour
Feb18
Music & 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. Sheffield
Hooch & Holler Comedy Show
Feb18
Music & 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 Division
Teatro Zinzanni
Feb19
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…

Thursday, February 19th
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Improvised Sketch Show
Feb19
Festivals, 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.
Dumb and Drummer
Feb19
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.
Improvsed DCOM
Feb19
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 St
Class! with Chad the Bird and Sara Benincasa
Feb19
Music & 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 Avenue
Love is Improvised
Feb19
Music & 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 Floor
Sketch Playlist
Feb19
Festivals, 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.
Roald Dahl’s The Enormous Crocodile: The Musical
Feb20
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 20th
Fine Arts Building | Studebaker Theater
410 South Michigan Avenue
The Infinite Wrench
Feb20
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…

Friday, February 20th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.