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
Chicago’s Best Comedy Show at The Comedy Bar
Feb22
Music & Comedy

Chicago’s Best Comedy Show at The Comedy Bar

Join Chicago’s best comedians for a hilarious night of stand-up comedy, pizza, and nonstop laughs!

Sunday, February 22nd
7:00 p.m.8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
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.
Late Nite Mic with Vik Pandya at The Comedy Bar
Feb23
Music & Comedy

Late Nite Mic with Vik Pandya at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Vik Pandya is a nationally touring…

Monday, February 23rd
7:00 p.m.9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
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
Tomato Throw Show at The Comedy Bar
Feb24
Music & 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 24th
7:00 p.m.9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Songwriter Circle w/ host Terry White and guests Ike & Shane Reilly
Feb24
Music & Comedy

Songwriter Circle w/ host Terry White and guests Ike & Shane Reilly

Chicago singer-songwriter Terry White continues his monthly ‘Songwriter Circle’ residency at Fitzgerald’s Sidebar with special guests Ike and Shane Reilly. This is a free event…

Tuesday, February 24th
7:00 p.m.9:00 p.m.
Fitzgerald’s
6615 Roosevelt Road
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
Crowd Work Wednesday at The Comedy Bar
Feb25
Music & 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 25th
7:00 p.m.9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
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
The Fizz Show
Feb25
Music & Comedy, Theatre & Performing Arts

The Fizz Show

Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…

Wednesday, February 25th
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
OhJay Lamont & Friends at The Comedy Bar
Feb26
Music & Comedy

OhJay Lamont & Friends at The Comedy Bar

2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry OhJay Lamont, born and raised on…

Thursday, February 26th
7:00 p.m.9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
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
Love Is Improvised: A Comedy Dating Show
Feb26
Music & Comedy, Theatre & Performing Arts, Tours & Attractions

Love Is Improvised: A Comedy Dating Show

Want a Date Night idea? Come laugh with love as we celebrate love and everything funny that comes with it! An improvised take on a…

Thursday, February 26th
8:30 p.m.9:30 p.m.
The Second City
230 W North Ave., 2nd Floor
Love Is Improvised: Season 2
Feb26
Music & Comedy, Theatre & Performing Arts

Love Is Improvised: Season 2

An improvised take on a hit reality-TV show that dares to ask… is love truly improvised? A cast of 10 improvisers will embark on a…

Thursday, February 26th
8:30 p.m.9:30 p.m.
The Second City
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 Dance Center and BraveSoul Movement present B-SERIES 2026: B-PRESENT BATTLE & JAM
Feb27
Festivals, 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 27th
11:00 a.m.12:30 p.m.
Columbia College Chicago Dance Center
1306 South Michigan Avenue
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.
The Rules of Bad Behavior
Feb27
Music & Comedy

The Rules of Bad Behavior

The Rules of Bad Behavior get recklessly applied to everything in this all-new, all-original sketch comedy revue. From awkward run-ins with Keanu Reeves at the…

Friday, February 27th
7:00 p.m.8:00 p.m.
The Den Theatre
1331 North Milwaukee Avenue