events-cat-music-comedy

Upcoming Chicago Events

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October 24, 2026: Oct24
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…
Old Town
Event details
Saturday, October 24th
3:00 p.m. – 4:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct24
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…
Event details
Saturday, October 24th
3:00 p.m. – 6:00 p.m.
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eta Creative Arts Foundation
7558 S South Chicago Ave
Oct24
Music & Comedy
The Wrecks – Finally : OUTSIDE Tour
Alternative rock band The Wrecks will bring their national fall headline run, the “Finally : OUTSIDE Tour,” to the House of Blues Chicago on Saturday,…
River North
Event details
Saturday, October 24th
5:00 p.m. – 9:00 p.m.
House of Blues
Oct24
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,…
Event details
Saturday, October 24th
6:00 p.m. – 7:00 p.m.
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de Maat Theatre at Second City
230 W North Ave
Oct24
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.…
Event details
Saturday, October 24th
6:00 p.m. – 7:00 p.m.
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The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,
Oct24
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…
Lincoln Park
Event details
Saturday, October 24th
6:00 p.m. – 7:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct24
Music & Comedy, Theatre & Performing Arts
“Hollywood Hit” at Dinner Detective Chicago
The Dinner Detective is an interactive comedic true crime dinner theatre experience based on real cold cases. Feast on dinner, but beware… the killer is…
Event details
Saturday, October 24th
6:00 p.m. – 9:00 p.m.
Courtyard by Marriott Chicago Downtown Magnificent Mile
165 E Ontario St
Oct24
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…
Old Town
Event details
Saturday, October 24th
6:30 p.m. – 8:00 p.m.
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The Second City
1616 N. Wells St.
Oct24
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…
Old Town
Event details
Saturday, October 24th
7:00 p.m. – 8:00 p.m.
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The Second City
230 W North Ave., 2nd Floor
Oct24
Music & Comedy
Zar the Star at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Zar the Star is a New…
River North
Event details
Saturday, October 24th
7:00 p.m. – 8:30 p.m.
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The Comedy Bar
162 E Superior St, Chicago, IL 60611
Oct24
Music & Comedy, Theatre & Performing Arts
University Symphony Orchestra: Annual Halloween Concerts
Pictures of the Imagination Colorful, exuberant, and sometimes scary musical pictures by Franz Liszt, Anatol Liadov, and George Whitefield Chadwick spur the imagination – and…
Event details
Saturday, October 24th
7:00 p.m. – 9:00 p.m.
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Mandel Hall, University of Chicago
1131 East 57th Street
Oct24
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…
Lincoln Park
Event details
Saturday, October 24th
7:30 p.m. – 8:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct24
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…
Event details
Saturday, October 24th
7:30 p.m. – 8:55 p.m.
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Apollo Theater
2550 N. Lincoln Ave.
Oct24
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…
Lincoln Park
Event details
Saturday, October 24th
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct24
Music & Comedy, Theatre & Performing Arts
Sleeping Beauty & Dvořák Cello Concerto
The crown jewel of cello repertoire, Dvořák’s heroic and soulful Cello Concerto marks the return of Jian Wang, a soloist with a lustrous sound and…
Loop
Event details
Saturday, October 24th
7:30 p.m. – 9:30 p.m.
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220 S. Michigan Ave.
Oct24
Music & Comedy
Tedeschi Trucks Band – Future Soul 2026 Tour
Award-winning blues-rock powerhouse The Tedeschi Trucks Band will conclude their “Future Soul 2026 Tour” with a four-night stand in Chicago in October 2026.
Loop
Event details
Saturday, October 24th
7:30 p.m. – 10:30 p.m.
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The Chicago Theatre
main stage is located at 2550 N. Lincoln Ave., Chicago, IL 60614
Oct24
Music & Comedy
Blondshell – Scaring Strangers Tour
Blondshell is scheduled to perform live in Chicago, Illinois on Saturday, October 24, 2026, as part of her newly announced “Scaring Strangers Tour”. Supporting Act:…
Event details
Saturday, October 24th
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Oct24
Music & Comedy
Edward Scissorhands In Concert
Released in 1990 and directed by Tim Burton (Beetlejuice, Disney Tim Burton’s The Nightmare Before Christmas), the film centers on Edward (Johnny Depp), a gentle…
Loop
Event details
Saturday, October 24th
7:30 p.m. – 10:30 p.m.
Auditorium
50 East Ida B. Wells Drive
Oct24
Music & Comedy
Thee Phantom and The Illharmonic Orchestra
Thee Phantom and The Illharmonic Orchestra will perform live at the Riviera Theatre in Chicago, Illinois, on October 24, 2026. Led by pioneering hip-hop maestro…
Uptown
Event details
Saturday, October 24th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Oct24
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…
Event details
Saturday, October 24th
7:30 p.m. – 10:30 p.m.
See all events in series
eta Creative Arts Foundation
7558 S South Chicago Ave
Oct24
Music & Comedy, Theatre & Performing Arts
Don Giovanni
The path to damnation never sounded so sweet The 2026/27 Season kicks off with a thrilling fable of deceit and retribution. Sharp humor, high drama,…
Loop
Event details
Saturday, October 24th
7:30 p.m. – 11:00 p.m.
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Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606
Oct24
Music & Comedy
Halloweensteen 2026 – Chicago, IL
The popular annual rock celebration Halloweensteen is returning to Chicago on Saturday, October 24, 2026. Hosted by South Side native singer-songwriter Michael McDermott, this festive…
Event details
Saturday, October 24th
7:30 p.m. – 11:00 p.m.
Park West
1901 W. Madison Street, Chicago
Oct24
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…
Old Town
Event details
Saturday, October 24th
8:00 p.m. – 9:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct24
Music & Comedy
Lupillo Rivera – 90’s CORRIDOS TOUR
Lupillo Rivera is bringing his 90’s CORRIDOS TOUR to the Rosemont Theatre on Saturday, October 24, 2026. This concert features a nostalgic lineup of regional…
Event details
Saturday, October 24th
8:00 p.m. – 11:00 p.m.
Rosemont Theatre

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