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ComedySportz Chicago
Apr25
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 April 25, 2026
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Puscifer Live at The Chicago Theatre – Normal Isn’t 2026 Tour
Apr25
Music & Comedy

Puscifer Live at The Chicago Theatre – Normal Isn’t 2026 Tour

Puscifer is scheduled to perform in Chicago on Saturday, April 25, 2026, at The Chicago Theatre. The show is part of the band’s “The Normal…

Saturday April 25, 2026
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
We Them Ones Comedy Tour: Mike Epps, Karlous Miller, DC Young Fly & Chico Bean
Apr25
Music & Comedy

We Them Ones Comedy Tour: Mike Epps, Karlous Miller, DC Young Fly & Chico Bean

Get ready for a night of non‑stop laughs as the We Them Ones Comedy Tour rolls into Chicago at the Wintrust Arena on Saturday, April 25, 2026!…

Saturday April 25, 2026
8:00 p.m.11:00 p.m.
Best Of Annoyance Sketch
Apr25
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 April 25, 2026
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Teatro Zinzanni
Apr26
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 April 26, 2026
4:00 p.m.7:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Wheel of Improv
Apr26
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 April 26, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Tuesday Good Show
Apr28
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 April 28, 2026
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Hooch & Holler Comedy Show
Apr29
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 April 29, 2026
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Teatro Zinzanni
Apr30
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 April 30, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Improvsed DCOM
Apr30
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 April 30, 2026
8:00 p.m.9:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
The Infinite Wrench
May1
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 May 1, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Teatro Zinzanni
May1
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…

Friday May 1, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Isaiah Collier: In Tribute to the Classics of John Coltrane
May1
Music & Comedy

Isaiah Collier: In Tribute to the Classics of John Coltrane

Isaiah Collier’s saxophone sound is both fierce and deeply reflective—rooted in tradition yet stretching toward the future. Named Chicago Tribune’s Jazz Artist of the Year and…

Friday May 1, 2026
7:30 p.m.9:00 p.m.
Reva and David – Logan Center for the Arts
915 E 60th St
Devil’s Daughter
May1
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 May 1, 2026
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
May1
Music & Comedy, Theatre & Performing Arts

Missed Call Sketch Comedy Show

Missed Call is a premier Chicago comedy group that writes and performs an entirely new sketch show every Friday — inspired by the audience’s suggestion!

Friday May 1, 2026
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Demi Lovato Live at United Center – It’s Not That Deep Tour 2026
May1
Music & Comedy

Demi Lovato Live at United Center – It’s Not That Deep Tour 2026

Award-winning diva Demi Lovato brings her powerhouse voice and fearless stage presence to Chicago on May 1, 2026, for a one-night-only performance at the United…

Friday May 1, 2026
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St.
Voila: The Improvised Musical
May1
Music & Comedy, Theatre & Performing Arts

Voila: The Improvised Musical

iO Chicago presents: a fully made-up, off-off-off Broadway style musical every Friday at 10pm in the Fremont Theater. Spend your Friday night with us. See…

Friday May 1, 2026
10:00 p.m.11:30 p.m.
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
Hitch*Cocktails
May1
Music & Comedy, Theatre & Performing Arts

Hitch*Cocktails

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together…

Friday May 1, 2026
10:00 p.m.11:30 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
The Infinite Wrench
May2
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…

Saturday May 2, 2026
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Matteo Lane – We Gotta Catch Up! Tour
May2
Music & Comedy

Matteo Lane – We Gotta Catch Up! Tour

Matteo Lane is bringing his much‑anticipated “We Gotta Catch Up!” comedy tour to Chicago, performing at the historic The Chicago Theatre on May 2, 2026 at 7:00 PM. Hailing from the Chicago area,…

Saturday May 2, 2026
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
Teatro Zinzanni
May2
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…

Saturday May 2, 2026
7:00 p.m.10:00 p.m.
Teatro ZinZanni – Cambria Hotel
32 W Randolph St
Baby Wants Candy! The Original Completely Improvised Musical
May2
Music & Comedy, Theatre & Performing Arts

Baby Wants Candy! The Original Completely Improvised Musical

“CRITICS’ PICK. TRULY AMAZING!” – New York Times “BEST VISITING IMPROV COMEDY!”– TimeOut NY “HIGHLY RECOMMENDED!” – The Onion “★★★★★” THEY ARE AN ENTERTAINMENT PHENOMENON AND I…

Saturday May 2, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St.
Clued In
May2
Music & Comedy, Theatre & Performing Arts

Clued In

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of…

Saturday May 2, 2026
7:30 p.m.8:30 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Katt Williams – Heaven On Earth Tour
May2
Music & Comedy

Katt Williams – Heaven On Earth Tour

On the heels of his explosive Netflix comedy special, WOKE FOKE, critically acclaimed comedian Katt Williams announces the HEAVEN ON EARTH TOUR. The upcoming tour…

Saturday May 2, 2026
8:00 p.m.11:00 p.m.
United Center
1901 W Madison St.
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