The Swingin’ Sisters: Suite!
May14
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

The Swingin’ Sisters: Suite!

The “Swingin’ Sisters! When Carolyn Broquet, Tirzah Joy and Barbara Smith join voices then the magic happens. Their repertoire from the Boswell Sisters, and the…

Thursday, May 14th
7:30 p.m.
The Checkout
4116 N. Clark St.
Dark Side of the Pillow Sketch Comedy Show
May14
Music & Comedy, Theatre & Performing Arts

Dark Side of the Pillow Sketch Comedy Show

The thoughts you have at 2 a.m.? We put them on stage. Looking for a night out that feels unmistakably Chicago? Dark Side of the…

Thursday, May 14th
7:30 p.m.8:30 p.m.
The De Matt Theater at The Second City
230 W North Ave
“Going Bacharach” Presents the Greatest Hits of Bacharach at the Apollo Theater
May14
Music & Comedy, Theatre & Performing Arts

“Going Bacharach” Presents the Greatest Hits of Bacharach at the Apollo Theater

Rediscover the soundtrack of a lifetime with GOING BACHARACH, a vibrant new revue, direct from a sold-out run in New York, celebrating the legacy of…

Thursday, May 14th
7:30 p.m.9:30 p.m.
Apollo Theater
2550 N. Lincoln Ave.
Elisa Carlson — Piano Bar
May14
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Elisa Carlson — Piano Bar

Elisa Carlson is an accomplished singer/multi-instrumentalist who performs as a piano bar entertainer in Chicago and around the world. She specializes in high-energy, request-driven, sing-along…

Thursday, May 14th
7:30 p.m.11:30 p.m.
The Redhead Piano Bar
16 W Ontario st
Cosmic Comedy Hour
May14
Music & Comedy

Cosmic Comedy Hour

Cosmic Comedy Hour is a one-hour live comedy show that combines magic, improv, and theatrical comedy into one fast-paced experience. Unlike traditional comedy shows, this…

Thursday, May 14th
8:00 p.m.9:00 p.m.
cosmic underground theater
3433 W Fullerton Ave
Picardía: Comedia Estandup en Español
May14
Music & Comedy

Picardía: Comedia Estandup en Español

Picardía los invita a reir y disfrutar de la comedia estandup en su idioma: ¡ el Español Picardía: Comedia Estandup en Español les presenta a los mejores…

Thursday, May 14th
8:00 p.m.9:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
moonwatchers
May14
May31
Music & Comedy, Theatre & Performing Arts

moonwatchers

It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…

Thursday, May 14th
8:00 p.m.Sunday, May 31st
2:30 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Roast Battle at Zanies
May14
Music & Comedy

Roast Battle at Zanies

Roast Battle Is @ Zanies Chicago! From the hit Comedy Central series, Roast Battle, brought to you by the team with over 200,000 online followers, Roast Battle…

Thursday, May 14th
9:00 p.m.11:00 p.m.
Zanies Comedy Club
5437 Park Place
Bring Me The Horizon – Ascension Program 2 Tour
May15
Music & Comedy

Bring Me The Horizon – Ascension Program 2 Tour

Bring Me The Horizon is scheduled to perform in Rosemont, IL, on Friday, May 15, 2026, at the Allstate Arena. The concert is part of…

Friday, May 15th
6:00 p.m.11:00 p.m.
Allstate Arena
6920 Mannheim Road
Dance Gavin Dance & The Fall of Troy
May15
Music & Comedy

Dance Gavin Dance & The Fall of Troy

Dance Gavin Dance is set to perform at the Riviera Theatre in Chicago on Friday, May 15, 2026. This date features special guests The Fall…

Friday, May 15th
6:00 p.m.11:00 p.m.
The Riveria Theater
4746 N Racine Ave
Lou Ella Rose and Friends — The Great Filipino Songbook
May15
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Lou Ella Rose and Friends — The Great Filipino Songbook

The Great Filipino Songbook beckons you into the Golden Age of Filipino song, where tender kundimans and stirring melodies shaped a people’s identity. Reimagined by…

Friday, May 15th
7:00 p.m.
Epiphany Center for the Arts
201 South Ashland Avenue
The Infinite Wrench
May15
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 15th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
Buena Onda Comedy
May15
Music & Comedy

Buena Onda Comedy

A stand-up show focused on highlighting Latin comedic talent and good vibes! Buena Onda turns two! Two years of risas, comunidad and good vibes Come…

Friday, May 15th
7:00 p.m.8:30 p.m.
The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United States
Big Dogs: Red Rocket
May15
Music & Comedy

Big Dogs: Red Rocket

The WINNERS of The Original Improv Gladiators, Season 39 are ready for their big mission; they’ll shoot for the moon, they’ll bring out all the…

Friday, May 15th
7:30 p.m.8:30 p.m.
Cornservatory
4210 N Lincoln Ave
Devil’s Daughter
May15
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 15th
7:30 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Lavelle Dontae at The Comedy Bar
May15
Music & Comedy

Lavelle Dontae at The Comedy Bar

2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Please note: This is a special…

Friday, May 15th
7:30 p.m.9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
“Going Bacharach” Presents the Greatest Hits of Bacharach at the Apollo Theater
May15
Music & Comedy, Theatre & Performing Arts

“Going Bacharach” Presents the Greatest Hits of Bacharach at the Apollo Theater

Rediscover the soundtrack of a lifetime with GOING BACHARACH, a vibrant new revue, direct from a sold-out run in New York, celebrating the legacy of…

Friday, May 15th
7:30 p.m.9:30 p.m.
Apollo Theater
2550 N. Lincoln Ave.
Charlie Puth – Whatever’s Clever! World Tour 2026
May15
Music & Comedy

Charlie Puth – Whatever’s Clever! World Tour 2026

Grammy-nominated singer-songwriter Charlie Puth is scheduled to perform at Rosemont Theatre on Friday, May 15, 2026, as part of his global “Whatever’s Clever! World Tour”.

Friday, May 15th
7:30 p.m.11:30 p.m.
Rosemont Theatre
Devil’s Daughter
May15
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 15th
8:00 p.m.9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Missed Call Sketch Comedy Show
May15
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 15th
8:00 p.m.9:00 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Qveen Herby – Isle of Qveen Tour
May15
Music & Comedy

Qveen Herby – Isle of Qveen Tour

Qveen Herby is bringing the “Isle of Qveen Tour” to the House of Blues Chicago on Friday, May 15, 2026. This all-ages performance features the…

Friday, May 15th
8:00 p.m.11:00 p.m.
moonwatchers
May15
Jun1
Music & Comedy, Theatre & Performing Arts

moonwatchers

It is Rocco and Allen’s job to watch the moon, and it is really quite boring. Night after night, they time the sequences exactly –…

Friday, May 15th
8:00 p.m.Monday, June 1st
2:30 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Honk! A Short Form Improv Show
May15
Music & Comedy, Theatre & Performing Arts

Honk! A Short Form Improv Show

Honk! is a short form, game-based improv show that asks: what good is comedy if you can’t get a little silly? Comprised of some of…

Friday, May 15th
9:00 p.m.10:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
420 Shakespeare
May15
Music & Comedy, Theatre & Performing Arts

420 Shakespeare

4 professional actors meet to perform a Shakespeare play… but only after one of them takes at least 20mg of you know what, leading to…

Friday, May 15th
9:00 p.m.10:30 p.m.
The De Matt Theater at The Second City
230 W North Ave