Improvised Jane Austen
Feb21
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.…

Saturday, February 21st
7:30 p.m.8:30 p.m.
iO Chicago
1501 N Kingsbury St,
The Original Improv Gladiators: Season 39
Feb21
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…

Saturday, February 21st
7:30 p.m.9:00 p.m.
Cornservatory
4210 N Lincoln Ave
The Kitty & Kellie Show
Feb21
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 Ave
ComedySportz Chicago
Feb21
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…

Saturday, February 21st
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Cosmic Underground Show
Feb21
Music & 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 Ave
Secret Sketch Show
Feb21
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 21st
9:00 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Best Of Annoyance Sketch
Feb21
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.
Teatro Zinzanni
Feb22
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. Randolph
Crashed Course History
Feb22
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 22nd
6:00 p.m.7:00 p.m.
The De Matt Theater at The Second City
230 W North Ave
Crashed Course History
Feb22
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 22nd
6:00 p.m.7:00 p.m.
The De Matt Theater at The Second City
230 W North Ave
Teatro Zinzanni
Feb22
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
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Wheel of Improv
Feb22
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 22nd
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Tuesday Good Show
Feb24
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 Ave
Comic Court: Chicago’s #1 Comedy Court Show
Feb24
Festivals, 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 Avenue
Andrea Bocelli: Romanza – 30th Anniversary World Tour
Feb25
Music & 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,
Hooch & Holler Comedy Show
Feb25
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 Division
Teatro Zinzanni
Feb26
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 26th
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Improvised Sketch Show
Feb26
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 26th
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Improvsed DCOM
Feb26
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 St
In the Realm of Senses presents: Myths & Legends
Feb26
Music & 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 Street
Love is Improvised
Feb26
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 26th
8:30 p.m.9:30 p.m.
Judy’s Beat Lounge
230 W. North Ave. 2nd Floor
Sketch Playlist
Feb26
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 26th
9:30 p.m.10:30 p.m.
iO Theater
1501 N. Kingsbury St.
The Infinite Wrench
Feb27
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.
ComedySportz Chicago
Feb27
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.