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
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.
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 Company
1501 N Kingsbury St
The Rules of Bad Behavior – A Sketch Comedy Show
Feb27
Music & Comedy

The Rules of Bad Behavior – A Sketch Comedy Show

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.8:30 p.m.
The Den Theatre
1331 North Milwaukee Avenue
Alex Quow at The Comedy Bar
Feb27
Music & Comedy

Alex Quow at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Alex Quow is a New York…

Friday, February 27th
7:00 p.m.9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Devil’s Daughter
Feb27
Music & Comedy

Devil’s Daughter

The hottest show in town, Devil’s Daughter, features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…

Friday, February 27th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
The Original Improv Gladiators: Season 39
Feb27
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…

Friday, February 27th
7:30 p.m.9:00 p.m.
Cornservatory
4210 N Lincoln Ave
The Addams Family Musical
Feb27
Music & Comedy, Theatre & Performing Arts

The Addams Family Musical

Blue Demon Theatre is proud to present THE ADDAMS FAMILY, a comical feast that embraces the wackiness in every family, features an original story and…

Friday, February 27th
7:30 p.m.10:00 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue