Upcoming Chicago Events
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Music & Comedy
Music & Comedy
Best of Second City
Find out for yourself why The Second City has been the first name in laughter for over sixty years! From the stages that launched the…
Music & Comedy, Theatre & Performing Arts, Tours & Attractions
The Cosmic Underground Show
Step aboard for a one-of-a-kind journey where mind-reading, magic, comedy, and sci-fi collide in ways you won’t find anywhere else in Chicago. Hosted by real-life…
Music & Comedy
Main Character Syndrome
Main Character Syndrome is a solo character showcase by Chicago’s funniest improvisers presenting original SNL-audition ready character sketches. From Tim Robinson to Cecily Strong, iO…
Music & Comedy
iO 45th Anniversary Saturday 1-Day Pass
In 1981, iO Theater started a revolution that shaped modern comedy and launched the sharpest, funniest voices in the industry. Join us November 5-7 as…
Music & Comedy, Theatre & Performing Arts
Pandemonium, Please Hold
The Second City’s 114th Mainstage Revue Pandemonium, Please Hold is a loud, fast, and gloriously unhinged night of comedic mayhem. The Second City’s six-person cast…
Music & Comedy
Standup Throw Down: Millennials vs Gen X
Millennials take on Generation X in a live stand-up comedy battle – and the audience decides who wins. Hosted by Chicago comedian Todd Glover, Standup…
Music & Comedy
3 Square Feat. D.A.R.E. Dropouts
Born out of the experimental genius of JTS Brown in 2002, 4 Square revolutionized long-form improvisation by stripping away sweep edits in favor of fluid…
Music & Comedy
Pandji Pragiwaksono at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Pandji Pragiwaksono Wongsoyudo is an Indonesian…
Music & Comedy
Zoltan Kaszas – Worldwide(ish) Tour
Zoltan Kaszas will bring his Worldwide(ish) Tour to Chicago on Saturday, November 7, 2026.
Music & Comedy
Ari Matti Live
Ari Matti is performing live in Chicago on Saturday, November 7, 2026, at The Vic Theatre. The Kill Tony regular and Estonian-born comedy powerhouse is…
Music & Comedy
Bert Kreischer – Permission To Party World Tour
Popular stand-up comedian and podcaster Bert Kreischer is bringing his shirt-off, high-energy storytelling to Chicago, Illinois, for back-to-back nights on Friday, November 6 and Saturday,…
Music & Comedy
Rickey Smiley: Rickey Smiley’s Karaoke Night – Chicago, IL
Legendary comedian, actor, and radio personality Rickey Smiley is bringing a unique night of comedy and music to Chicago on Saturday, November 7, 2026. The…
Music & Comedy
Ari Matti Live!
Estonian-born comedian and Kill Tony regular Ari Matti is bringing his bold, high-energy stand-up comedy to Chicago, Illinois, on Saturday, November 7, 2026, performing at…
Music & Comedy
iO 45th Anniversary – 3-Day Pass
In 1981, iO Theater started a revolution that shaped modern comedy and launched the sharpest, funniest voices in the industry. Join us November 5-7 as…
Music & Comedy
Saturday Night Sketch
Saturday Night Sketch brings Chicago’s best sketch comedy ensembles to the stage for a high-octane evening. From sharp political satire to mind melting absurdity, come…
Music & Comedy, Theatre & Performing Arts
Vape! The Grease Parody
Vape! lovingly pokes fun at all of the wonderful moments, sexual innuendos, outrageous characters, rivalries and secret romances from the original musical. The hair products may…
Music & Comedy
The Best of IO
Celebrate 45 years of improvisational excellence with the Best of iO Improv. This show brings together two teams of our very best improvisers, each delivering…
Music & Comedy, Theatre & Performing Arts
The Snow Queen
THE SNOW QUEENwritten by Mallory Swisherdirected & choreographed by Stefan Roseen & Anna Roemer Once there was, and once there was not, a little girl…
Music & Comedy, Theatre & Performing Arts
Beethoven 5 & Mao Fujita
Beethoven’s Fifth Symphony, with its iconic four-note motif, stands as a powerful testament to the resilience of the human spirit. Strauss’ Burlesque — written when the composer…
Music & Comedy
Sinatra ’56 – Songs for Swingin’ Lovers
Sinatra ’56 — Songs for Swingin’ Lovers is the third chapter in a trilogy of cabaret concerts celebrating Frank Sinatra’s remarkable Capitol-era comeback—and the moment…
Music & Comedy
Choral Showcase
University Chorale and University Singers present their annual fall Choral Showcase. Musicians: UNIVERSITY SINGERS Kaitlin Foley, conductor Chungho Lee, piano Ani Alloian, Abbie Bruce, Abhia…
Music & Comedy
Dave Matthews Band – Chicago, IL – 2026 Fall Tour
Dave Matthews Band will perform live at the United Center in Chicago, Illinois, on Saturday, November 7, 2026.The concert is a key stop on their…
Music & Comedy
Best of the Second City
Find out for yourself why The Second City has been the first name in laughter for over sixty years! From the stages that launched the…
Music & Comedy
The Naked Comedy Show
As seen in Axios Chicago, The New York Times, Time Out, NowThis News… Yup, it’s exactly what it sounds like. Top comics with no bottoms.…
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