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Music & Comedy
Sueños Music Festival 2026
The Sueños Music Festival celebrates its fifth anniversary in Grant Park, Chicago, on Saturday, May 23, and Sunday, May 24, 2026. This Memorial Day weekend…
Music & Comedy, Theatre & Performing Arts
Company
From musical theatre’s most renowned composer, Company is largely regarded as a trailblazer of the dark-comedy, modern-musical genre and the winner of six Tony Awards,…
Sunday, May 24th
2:30 p.m. – 5:00 p.m.Greenhouse Theater Center
2257 North Lincoln AvenueMusic & Comedy, Theatre & Performing Arts
Who’s Waldo?
Ten of Chicago’s best comedians and performers will rapid-fire take the stage as Waldo, and it’s up to the audience to figure out: Who’s Waldo?…
Sunday, May 24th
5:00 p.m. – 6:30 p.m.Lincoln Lodge, 2040 N Milwaukee Ave, Chicago, IL 60647
2040 N Milwaukee Ave, Chicago, IL 60647, United StatesMusic & Comedy
Thornhill – The Mercia Tour
Australian alternative metal band Thornhill is scheduled to perform in Chicago on May 24 as part of The Mercia Tour. Supporting Acts: 156/Silence, Fox Lake,…
Sunday, May 24th
6:00 p.m. – 11:00 p.m.The Vic Theatre
3145 N. SheffieldMusic & Comedy
UFO Case Files
Men in Black meets Whose Line Is It Anyways? UFO Case Files is a live improv show in Logan Square where the cast creates a…
Sunday, May 24th
7:00 p.m. – 8:00 p.m.cosmic underground theater
3433 W Fullerton AveMusic & Comedy
Chicago’s Best Comedy Show at The Comedy Bar
IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St. – The entrance to the venue is on Superior Street,…
Sunday, May 24th
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Festivals, Fairs & Special Events, Music & Comedy
Rockin’ in the Park 2026 Free Summer Concert Series
Rosemont’s Parkway Bank Park Entertainment District (5501 Park Place, Rosemont) will set the stage for another summer of live music with the return of its “Rockin’ in the…
Sunday, May 24th
7:00 p.m. – 10:00 p.m.Parkway Bank Park Entertainment District
5501 Park PlaceMusic & 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!)…
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, May 25th
7:00 p.m. – 9:00 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy, Theatre & Performing Arts
The Oldest Profession: Solo Comedy Show About Sex Worker History | Chicago
The Oldest Profession is a solo comedy show by Kaytlin Bailey — comedian, former sex worker, and host of the acclaimed podcast of the same…
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 26th
7:00 p.m. – 8:30 p.m.The Gallery Cabaret
2020 N Oakley AveMusic & 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, May 26th
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy, Theatre & Performing Arts
The Oldest Profession: Solo Comedy Show About Sex Worker History | Chicago
The Oldest Profession is a solo comedy show by Kaytlin Bailey — comedian, former sex worker, and host of the acclaimed podcast of the same…
Music & Comedy
Friendly Songwriter Spotlight Series – AJ Rosales
AJ’s style is not easy to classify, but his progressively acoustic tendencies tend to dominate his compositions. His rhythmic, expressive and emotive delivery gets peppered…
Tuesday, May 26th
7:00 p.m. – 9:00 p.m.Friendly Bar
6733 Roosevelt RdMusic & Comedy
Esteman & Daniela Spalla – Amorío USA Tour
Esteman and Daniela Spalla are performing together at the House of Blues Chicago on Tuesday, May 26, 2026, as part of their “Amorío USA Tour”.
Tuesday, May 26th
7:00 p.m. – 10:00 p.m.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 26th
9:00 p.m. – 10:30 p.m.The Lincoln Lodge
2040 N Milwaukee Ave, Chicago, IL 60647, United StatesMusic & 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, May 27th
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy, Theatre & Performing Arts
The Oldest Profession: Solo Comedy Show About Sex Worker History | Chicago
The Oldest Profession is a solo comedy show by Kaytlin Bailey — comedian, former sex worker, and host of the acclaimed podcast of the same…
Music & Comedy
A$AP Rocky – Don’t Be Dumb World Tour 2026
Hip-hop artist A$AP Rocky is scheduled to kick off his 42-date “Don’t Be Dumb World Tour” in Chicago on Wednesday, May 27, 2026. This tour…
Wednesday, May 27th
7:30 p.m. – 10:30 p.m.United Center
1901 W Madison St,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 27th
9:00 p.m. – 11:00 p.m.Bordel Cocktail & Cabaret
1721 W DivisionMusic & 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,…
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 28th
7:00 p.m. – 8:30 p.m.Morgan’s On Fulton
950 W Fulton MarketMusic & Comedy
Gigi LeFlair at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Gigi LeFlair is a rising star…
Thursday, May 28th
7:00 p.m. – 8:30 p.m.The Comedy Bar
162 E Superior St, Chicago, IL 60611Music & Comedy
Here Come The Mummies – 2026 Tour
Here Come The Mummies are performing at House of Blues Chicago on Thursday, May 28, 2026.
Thursday, May 28th
7:00 p.m. – 10:00 p.m.

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