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Upcoming Chicago Events
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Music & Comedy
Music & 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.…
Music & 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…
Music & 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…
Music & 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”.
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,…
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…
Music & 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…
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…
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,…
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…
Music & 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…
Music & Comedy
Here Come The Mummies – 2026 Tour
Here Come The Mummies are performing at House of Blues Chicago on Thursday, May 28, 2026.
Festivals, 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…
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…
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…
Music & Comedy
Comedy Bang! Bang! – Ground Beefing Tour
Comedy Bang! Bang! Live! is scheduled to bring the Ground Beefing Tour 2026 to Chicago on Thursday, May 28, 2026. Hosted by Scott Aukerman, featuring…
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Crème de la Femme: An All-Femme Improv Festival
Finally, women are funny! On Friday, May 29 and Saturday, May 30, iO Theater is hosting Crème de la Femme: An All-Femme Improv Festival. As…
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…
Music & Comedy
Kerwin Claiborne at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Kerwin Claiborne is a well-known Instagram…
Music & Comedy, Theatre & Performing Arts
The Last Word
The Last Word is the first 4 course craft cocktail progression paired with a screenplay. 6 actors come on stage and read through a high…
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.…
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