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Music & Comedy
Music & Comedy
Stephen Kohler and Rob Klegon Matinee Show
Following an in-studio performance on the WGN Midday News on Monday, Oct 5, Chicago singer-songwriter Stephen Kohler and percussionist Rob Klegon will perform a set…
Music & Comedy
Bad Momz of Comedy at The Comedy Bar
Your Saturday brunch plans just got a whole lot better! Bad Momz of Comedy is taking over Comedy Bar on October 17 for a ONE-TIME-ONLY…
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
Black Latina (The Play) Comes to Chicago
After more than a decade of touring nationally, Black Latina (The Play) comes to Chicago for a limited three-day run, October 16–18, 2026. Written by…
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
DETROIT ’67
Detroit ’67 A Play by Dominique Morisseau Directed by Aaron Reese Boseman Running through November 1, 2026 ★★★★ “HIGHLY RECOMMENDED. THE CAST IS FIRE!” –Bonnie…
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
420 Frankenstein
The creator of 420 Shakespeare is bringing Mary Shelley’s monster to life… with a little help from Mary Jane. On a dark and stormy night,…
Music & Comedy, Theatre & Performing Arts
Scott Green Lies To Your Kids
The Kids Show For Adults. It’s the all-ages magic show that’s actually fun for all ages. This is not a sweet, gentle, clap-along children’s show.…
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, 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
Knox – Chicago – My Midwest Best World Tour
Rising pop/country singer-songwriter Knox (Knox Morris) will perform live in Chicago on Saturday, October 17, 2026, at the House of Blues Chicago. The concert is…
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
Joey Bragg at The Comedy Bar
After wrapping the final season of Disney Channel’s top-rated show, LIV AND MADDIE, Joey Bragg has been incredibly busy establishing himself as a comedic leading…
Music & Comedy, Theatre & Performing Arts
The Second City Improv Social at Sheraton Grand Chicago Riverwalk
Enjoy a 90-minute improv experience with The Second City, plus two cocktails and small bites for $110. Looking for a unique way to spend your…
Music & Comedy, Theatre & Performing Arts
Black Latina (The Play) Comes to Chicago
After more than a decade of touring nationally, Black Latina (The Play) comes to Chicago for a limited three-day run, October 16–18, 2026. Written by…
Music & Comedy
Ben Schwartz & Friends
Ben Schwartz is bringing his “Ben Schwartz & Friends” tour to Chicago for a night of unscripted improv comedy in the fall of 2026.
Music & Comedy
Catch Your Breath – Not Broken Enough Tour
Catch Your Breath will perform live in Chicago on Saturday, October 17, 2026, as part of their “Not Broken Enough Tour”. Supporting Lineup: This heavy…
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
Guerrero Leads Fandangos & Enigma Variations
Few contemporary violin concertos have made a splash with audiences like Arturo Márquez’s Fandango, which won a 2024 Latin Grammy. Composed for Anne Akiko Meyers, this…
Music & Comedy
Suki Waterhouse – The Loveland Tour
Suki Waterhouse will conclude her North American tour in Chicago on Saturday, October 17, 2026. This show at the Byline Bank Aragon Ballroom is part…
Music & Comedy
Judah and The Lion – 2026 Tour
Alternative folk-pop band Judah & The Lion will bring their headline tour to Chicago on Saturday, October 17, 2026. The performance is part of their…
Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
DETROIT ’67
Detroit ’67 A Play by Dominique Morisseau Directed by Aaron Reese Boseman Running through November 1, 2026 ★★★★ “HIGHLY RECOMMENDED. THE CAST IS FIRE!” –Bonnie…
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