moonwatchers
May10
May27
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 –…

Sunday, May 10th
8:00 p.m.Wednesday, May 27th
2:30 p.m.
Greenhouse Theater Center
2257 North Lincoln Avenue
Chicago Cabaret Professionals presents Musical Mondays: Tony Bennett at 100
May11
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Chicago Cabaret Professionals presents Musical Mondays: Tony Bennett at 100

Join us as we celebrate the 100th birthday of the one and only Tony Bennett! This Chicago Cabaret Week show highlights his incredible musical legacy,…

Monday, May 11th
7:30 p.m.
The Rhapsody Theater
1328 W Morse Ave
Girls Like Us — It’s My Party: Celebrating the Girls and the Groups of the 1960s
May12
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Girls Like Us — It’s My Party: Celebrating the Girls and the Groups of the 1960s

When we talk about music of the 1960s, most people think of Bob Dylan, The Beatles, Jimi Hendrix and the Rolling Stones — but that’s…

Tuesday, May 12th
7:00 p.m.
PianoForte Chicago
1335 South Michigan Avenue
Tuesday Good Show
May12
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, May 12th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
The Beaus — Mashups and More
May12
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

The Beaus — Mashups and More

Prepare to be captivated by the harmonious melodies and infectious energy of The Beaus, Chicago’s favorite MAN-band. Their tight harmonies resonate through the room, enveloping…

Tuesday, May 12th
7:00 p.m.10:00 p.m.
Stars & Garters
3914 N Clark St
Comic Court: Chicago’s #1 Comedy Court Show
May12
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, May 12th
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Hilary Ann Feldman — The Life & Laughs of Carol Burnett
May13
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Hilary Ann Feldman — The Life & Laughs of Carol Burnett

The world has loved Carol Burnett for over fifty years. Her fearless character acting and self-effacing personality made her Lucille Ball’s successor as the Queen…

Wednesday, May 13th
7:00 p.m.
Borelli’s Pizza
2124 W Lawrence Ave
24WORDS Production —The Day Before Remember When: An Equal Rights journey
May13
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

24WORDS Production —The Day Before Remember When: An Equal Rights journey

Vibrant, funny, and inspirational, The Day Before Remember When is a cabaret about a 300-year odyssey to achieve Equality. With 15 original songs based on…

Wednesday, May 13th
7:30 p.m.9:30 p.m.
Bughouse Theater
1910 West Irving Park Road
Rodrigo Y Gabriela – 20th Anniversary Tour
May13
Music & Comedy

Rodrigo Y Gabriela – 20th Anniversary Tour

Rodrigo y Gabriela are scheduled to perform in Chicago, IL, on Wednesday, May 13, 2026, as part of their “20th Anniversary Tour”.

Wednesday, May 13th
7:30 p.m.10:30 p.m.
The Chicago Theatre
175 N. State
Triumph Live In Chicago – 50th Anniversary Tour
May13
Music & Comedy

Triumph Live In Chicago – 50th Anniversary Tour

Canadian rock legends Triumph /w special guests April Wine will perform live at Rosemont Theatre on May 13, 2026.

Wednesday, May 13th
8:00 p.m.10:00 p.m.
Rosemont Theatre
Hooch & Holler Comedy Show
May13
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, May 13th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
The Fizz Show
May13
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, May 13th
10:00 p.m.11:00 p.m.
iO Theater
1501 N. Kingsbury St.
Morgan’s Laugh Lounge
May14
Music & Comedy

Morgan’s Laugh Lounge

Laugh your way into your new favorite Thursday tradition at Morgan’s Laugh Lounge, Chicago’s newest comedy hotspot. Every Thursday night from 6:00–9:30 PM, the lounge…

Thursday, May 14th
7:00 p.m.8:30 p.m.
Morgan’s On Fulton
950 W Fulton Market
Anne Burnell — Cry Me a River: The Music of Julie London
May14
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

Anne Burnell — Cry Me a River: The Music of Julie London

Julie London was an American singer, a film and TV actress, and a pinup model, whose career spanned five decades. She released over 30 albums…

Thursday, May 14th
7:00 p.m.9:00 p.m.
Gateway Theater Annex @ The Copernicus Center
5216 W Lawrence Ave.
The Peppermint Patties — Love You (Hate You) Mean It
May14
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts

The Peppermint Patties — Love You (Hate You) Mean It

The Peppermint Patties are a vocal quartet specializing in close-harmony cabaret performances and Love You (Hate You) Mean It is a journey through the highs,…

Thursday, May 14th
7:30 p.m.
Hey Nonny
10 S. Vail Ave.
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
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
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
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.
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.