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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.…
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
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 21st
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 21st
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 21st
8:00 p.m. – 9:30 p.m.cosmic underground theater
3433 W Fullerton AveMusic & 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 21st
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 21st
9:30 p.m. – 10:30 p.m.The Annoyance Theatre
851 W. Belmont Ave.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 22nd
4:00 p.m. – 7:00 p.m.Spiegeltent – Cambria Hotel
32 W. RandolphMusic & 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 22nd
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 22nd
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 22nd
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
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 24th
7:00 p.m. – 8:30 p.m.The Gallery Cabaret
2020 N Oakley AveFestivals, 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 24th
9:00 p.m. – 10:30 p.m.The Lincoln Lodge
2040 North Milwaukee AvenueMusic & Comedy
Andrea Bocelli: Romanza – 30th Anniversary World Tour
Andrea Bocelli is scheduled to perform in Chicago at the United Center on February 25, 2026, as part of his Romanza—30th Anniversary World Tour.
Wednesday, February 25th
8:00 p.m. – 11:00 p.m.United Center
1901 W Madison St,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 25th
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 26th
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 26th
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 26th
8:00 p.m. – 9:00 p.m.Malarkey Comedy Company
1501 N Kingsbury StMusic & Comedy, Theatre & Performing Arts
In the Realm of Senses presents: Myths & Legends
In the Realm of Senses: Myths & Legends is an immersive concert experience where ancient stories are reimagined through sound, sight, movement, and scent. Featuring…
Thursday, February 26th
8:00 p.m. – 10:00 p.m.Chopin Theatre
1543 West Division StreetMusic & 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 26th
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 26th
9:30 p.m. – 10:30 p.m.iO Theater
1501 N. Kingsbury St.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 27th
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.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…
Friday, February 27th
7:00 p.m. – 8:30 p.m.Malarkey Comedy
1501 N. Kingsbury St.

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