Upcoming Chicago Events
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Music & Comedy
Music & Comedy
Hyde Park Jazz Festival 2026
The Hyde Park Jazz Festival returns Saturday and Sunday, September 26 and 27, 2026, across multiple Hyde Park venues on Chicago’s South Side. The organizer…
Festivals, Fairs & Special Events, Music & Comedy, Sports & Recreation
WingOut Chicago 2026
WingOut Chicago | Sept 26-27 | Gallagher Way • Chicago Join us at Gallagher Way in Wrigleyville for Chicago’s most mouth-watering outdoor event of the…
Music & Comedy
Paige Kizer ‘Unconditional’ Album Release Show
Chicago singer-songwriter Paige Kizer’s debut album Unconditional is set for release on Friday, Sept 25, and she and her band will be celebrating the release…
Music & Comedy
Lucy Darling – Chicago, IL – Simply Darling Tour
The award-winning magician and comedian Lucy Darling (the glamorous, 1940s-style socialite character created by Carisa Hendrix) will perform a series of intimate live shows at…
Music & Comedy
Dying Fetus & Sanguisugabogg – 2026 Tour
Dying Fetus and Sanguisugabogg are bringing their co-headlining tour to the House of Blues Chicago on Sunday, September 27, 2026. Supporting Acts: Crowbar, Left to…
Music & Comedy
Marquee: Musical Improv
Musical theatre and improv collide as Marquee presents you with an hour of fully improvised musical comedy, spontaneously creating entire scenes, songs, and stories based…
Music & Comedy
Illinois Rock and Roll Hall of Fame Induction Ceremony
Hosted by the Illinois Rock & Roll Museum on Route 66, this annual celebration honors the legendary artists, broadcasters, and industry leaders who shaped Illinois’…
Museums, Galleries & Exhibitions, Music & Comedy
Illinois Rock and Roll Hall of Fame Induction Ceremomy
Celebrate Illinois’ legendary music history at the Illinois Rock & Roll Hall of Fame Induction Ceremony, held at the Harris Theater in Millennium Park. This…
Music & Comedy
Jay Washington at The Comedy Bar
From the ring to the mic, Jay Washington trades body slams for punchlines! This high-energy stand-up comedian, actor, and host is a force of nature.…
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, Theatre & Performing Arts
The Aviary: Birds of Paradise
Join producers Hummingbird of Pollinator Entertainment Group and Gaybriel Le Fae of Fae Productions for a night of enchanting burlesque at Chicago’s Newport Theater! Starring:…
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
Harold Night
See the show that started it all, and experience the iO Theater’s groundbreaking, signature improv form: The Harold! This long-running, weekly improv tradition is double-headlined…
Music & Comedy
Bryson Tiller – The Neo Trapsoul Tour
Bryson Tiller is performing live in Tinley Park on Sunday, September 27, 2026, as a headlining stop on “The Neo Trapsoul Tour”.
Music & Comedy
Kylie Cantrall – Chicago, IL – The Valley Girl Problems Tour
Disney star and pop artist Kylie Cantrall is performing live in Chicago, Illinois on Sunday, September 27, 2026. The concert marks the second official stop…
Music & Comedy
Deep Schwa
Chicago’s longest-running Harold team returns to iO to bring their unique blend of chaos and creativity to iO’s signature form The Harold melding games, songs, and scenes…
Music & Comedy, Theatre & Performing Arts
Who’s Waldo?
Who’s Waldo? is a comedy variety show where everyone (local and touring comedians, clowns, musicians, and – yes, even you) is Waldo. Part comedy show,…
Music & Comedy
Cavetown – Running With Scissors Tour
Cavetown is bringing the Running With Scissors Tour to The Salt Shed in Chicago on Sunday, September 27, 2026.
Music & Comedy
Sara Bareilles – Good Grief Tour
Sara Bareilles will perform live at The Chicago Theatre on Sunday, September 27, 2026, as part of her newly announced “The Good Grief Tour”. The…
Music & Comedy
Mike Samp at The Comedy Bar
Hailing from Chicago’s South Side, Mike Samp (often fast-typed as Nike Samp) is an explosive force in the comedy scene. Rising to prominence with his…
Music & Comedy
The 11pm Show
Continuing the rich tradition of late night improv, join the veteran cast of THE 11PM SHOW every Friday at 11PM as they perform late night, artistic improv…
Music & Comedy
The Armando Diaz
It’s the best comedy show in the city. Created in 1995 by iO alum Armando Diaz, Armando is a historic improvisational form where actors improvise a series…
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
Chelsea Wolfe – THE DARK World Tour
Singer-songwriter Chelsea Wolfe will perform live in Chicago on Monday, September 28, 2026 at the Riviera Theatre. The performance is part of her newly announced…
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