events-cat-music-comedy

Upcoming Chicago Events

Check out what's happening all around Chicago.

October 25, 2026: Oct25
Music & Comedy, Theatre & Performing Arts
Omar
Where memory is preserved, legacy endures. MacArthur “Genius Grant” recipient Rhiannon Giddens and celebrated co-composer Michael Abels deliver a profoundly moving story about the strength…
Loop
Event details
Sunday, October 25th
2:00 p.m. – 4:30 p.m.
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Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606
Oct25
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
Sunday, October 25th
3:00 p.m. – 5:00 p.m.
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220 S. Michigan Ave.
Oct25
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
Sunday, October 25th
3:00 p.m. – 6:00 p.m.
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eta Creative Arts Foundation
7558 S South Chicago Ave
Oct25
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…
Lincoln Park
Event details
Sunday, October 25th
6:00 p.m. – 7:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct25
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
Sunday, October 25th
7:00 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Oct25
Music & Comedy
Brett Goldstein – Chicago, IL – Sex, Death & Small Talk Tour
Brett Goldstein is bringing his brand-new stand-up comedy tour, “Sex, Death & Small Talk,” to Chicago on Sunday, October 25, 2026, at 7:00 PM.
Loop
Event details
Sunday, October 25th
7:00 p.m. – 9:00 p.m.
The Chicago Theatre
main stage is located at 2550 N. Lincoln Ave., Chicago, IL 60614
Oct25
Music & Comedy
The Longest Johns Live In Concert
The Longest Johns are performing live in Chicago on Sunday, October 25, 2026, at The Vic Theatre. The English folk band, famous for spearheading the…
Event details
Sunday, October 25th
7:00 p.m. – 10:00 p.m.
The Vic Theatre
3145 N. Sheffield
Oct25
Music & Comedy
Sleeping With Sirens – An Ending In Itself Tour
Alternative rock band Sleeping With Sirens will bring their headline An Ending In Itself Tour to Chicago on Sunday, October 25, 2026. The newly announced…
Event details
Sunday, October 25th
7:00 p.m. – 10:00 p.m.
The Salt Shed
1357 N Elston
Oct25
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
Sunday, October 25th
7:30 p.m. – 8:55 p.m.
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Apollo Theater
2550 N. Lincoln Ave.
Oct25
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…
Lincoln Park
Event details
Sunday, October 25th
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct25
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…
Lincoln Park
Event details
Sunday, October 25th
8:00 p.m. – 9:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct25
Music & Comedy
Matt Rife Live In Chicago – Stay Golden 2025-26 World Tour
Comedian Matt Rife will perform live at Chicago’s United Center on Oct. 25, 2026.
West Loop
Event details
Sunday, October 25th
8:00 p.m. – 10:00 p.m.
United Center
1901 W Madison St,
Oct25
Oct26
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…
Lincoln Park
Event details
Sunday, October 25th
11:00 p.m. – Monday, October 26th
12:00 a.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
October 26, 2026: Oct26
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…
Lincoln Park
Event details
Monday, October 26th
7:00 p.m. – 8:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct26
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
Monday, October 26th
7:00 p.m. – 8:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct26
Music & Comedy
Late Nite Mic with Vik Pandya at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Vik Pandya is a nationally touring…
River North
Event details
Monday, October 26th
7:00 p.m. – 9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Oct26
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
Monday, October 26th
7:30 p.m. – 10:30 p.m.
See all events in series
The Chicago Theatre
main stage is located at 2550 N. Lincoln Ave., Chicago, IL 60614
Oct26
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
Monday, October 26th
7:30 p.m. – 10:30 p.m.
See all events in series
eta Creative Arts Foundation
7558 S South Chicago Ave
Oct26
Music & Comedy
She Wants Revenge – 2026 Tour
She Wants Revenge is performing at the House of Blues Chicago on Monday, October 26, 2026. Special Guest: Rosegarden Funeral Party.
River North
Event details
Monday, October 26th
8:00 p.m. – 11:00 p.m.
House of Blues
Oct26
Music & Comedy
$10 Improv Night
All the cool kids stay out late on a school night! Join new teams as they deliver a short and sweet show filled with laughter…
Lincoln Park
Event details
Monday, October 26th
9:00 p.m. – 10:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Oct26
Oct27
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…
Lincoln Park
Event details
Monday, October 26th
11:00 p.m. – Tuesday, October 27th
12:00 a.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
October 27, 2026: Oct27
Music & Comedy
SiM – Hooman After All World Tour
Japanese reggae-punk and metal band SiM is scheduled to perform live in Chicago, Illinois on Tuesday, October 27, 2026, as part of their newly announced…
River North
Event details
Tuesday, October 27th
6:30 p.m. – 9:30 p.m.
House of Blues
Oct27
Music & Comedy
Guy’z Nite Comedy Show at The Comedy Bar
Guy’z Nite is a wildly known weekly sold out comedy show headlined by Guy Reuven, starring NEW celebrity lineups of Hollywood’s BIGGEST comedians including Ismo,…
River North
Event details
Tuesday, October 27th
7:00 p.m. – 9:00 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Oct27
Music & Comedy
Joanne Mcnally – Pinotphile Tour
Joanne McNally is performing live in Chicago on Tuesday, October 27, 2026, as part of her hotly anticipated new North American stand-up comedy tour, “Pinotphile”.
Event details
Tuesday, October 27th
7:30 p.m. – 9:30 p.m.
The Vic Theatre
3145 N. Sheffield

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