Best of Chicago Comedy – Chicago
Sep24
Music & Comedy

Best of Chicago Comedy – Chicago

Get ready to laugh your heart out at the “Best of Chicago Comedy – Chicago” show, happening at the vibrant Foundation Room at House Of…

Thursday, September 24th
The Foundation Room at House Of Blues – Chicago
329 N Dearborn St, Chicago,
Xavier Wulf – The Cool World Tour
Sep24
Music & Comedy

Xavier Wulf – The Cool World Tour

Underground rap sensation Xavier Wulf is bringing his newly announced headlining run, “The Cool World Tour,” to Chicago, Illinois on Thursday, September 24, 2026. The…

Thursday, September 24th
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Sketch Playlist
Sep24
Music & Comedy, Theatre & Performing Arts

Sketch Playlist

Nominated “Best Comedy Show” by the Chicago Reader (2025), Sketch Playlist is a weekly sketch show that will feature all-new sketches every single week… the…

Thursday, September 24th
9:30 p.m. – 10:30 p.m.
iO Theater
1501 N. Kingsbury St.
Blueprint
Sep24
Music & Comedy

Blueprint

Blueprint is the kind of improv that keeps audiences AND players on their toes. Each week, a different cast member designs a bold new improv format…

Thursday, September 24th
10:00 p.m. – 11:00 p.m.
iO Theater
1501 N. Kingsbury St.
The 11pm Show
Sep24
Sep25
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…

Thursday, September 24th
11:00 p.m. – Friday, September 25th
12:00 a.m.
iO Theater
1501 N. Kingsbury St.
Mäkelä Conducts Sibelius & Shostakovich
Sep25
Music & Comedy, Theatre & Performing Arts

Mäkelä Conducts Sibelius & Shostakovich

Two exhilarating symphonies launch the fall residency of Zell Music Director Designate Klaus Mäkelä. Sibelius’ Seventh Symphony sweeps you along like a mighty river flowing…

Friday, September 25th
1:30 p.m. – 3:30 p.m.

220 S. Michigan Ave.
Lucy Darling – Chicago, IL – Simply Darling Tour
Sep25
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…

Friday, September 25th
5:30 p.m. – 10:30 p.m.
Studebaker Theater
410 South Michigan Avenue Fine Arts Building
World Music Festival Chicago
Sep25
Sep26
Festivals, Fairs & Special Events, Music & Comedy

World Music Festival Chicago

Ragamala: A Celebration of Indian Classical Music Returning for its 14th year, the country’s largest all-night presentation kicks off with live Indian classical music for…

Friday, September 25th
6:00 p.m. – Saturday, September 26th
8:00 a.m.
Chicago Cultural Center
78 E. Washington Street
Pandemonium, Please Hold
Sep25
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…

Friday, September 25th
6:30 p.m. – 8:00 p.m.
The Second City
1616 N. Wells St.
Teddy Swims – The Ugly Tour
Sep25
Music & Comedy

Teddy Swims – The Ugly Tour

Teddy Swims is bringing his The UGLY Tour to the United Center in Chicago on Friday, September 25, 2026. Support: Featuring special guest Freak Freely.

Friday, September 25th
7:00 p.m. – 10:00 p.m.
United Center
1901 W. Madison Street, Chicago
Sofi Tukker – Animal Talk Tour
Sep25
Music & Comedy

Sofi Tukker – Animal Talk Tour

Sofi Tukker is bringing their “Animal Talk” tour to the Huntington Bank Pavilion at Northerly Island on Friday, September 25, 2026. Special Guest: Kungs.

Friday, September 25th
7:00 p.m. – 10:00 p.m.
Polyphia – MMXXVI Tour
Sep25
Music & Comedy

Polyphia – MMXXVI Tour

Instrumental rock band Polyphia will perform live in Chicago on Friday, September 25, 2026, at the Aragon Ballroom. The concert is a headline stop on…

Friday, September 25th
7:00 p.m. – 10:00 p.m.
Aragon Ballroom
1106 W. Lawrence Ave., Chicago, IL 60640
Vape! The Grease Parody
Sep25
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…

Friday, September 25th
7:30 p.m. – 8:55 p.m.
Apollo Theater
2550 N. Lincoln Ave.
Devil’s Daughter
Sep25
Music & Comedy

Devil’s Daughter

The hottest show in town, Devil’s Daughter, features a cast of seasoned comedians who have performed together in Chicago and around the country for over a…

Friday, September 25th
7:30 p.m. – 9:00 p.m.
iO Theater
1501 N. Kingsbury St.
Laura Ramoso – The Calm Down Tour
Sep25
Music & Comedy

Laura Ramoso – The Calm Down Tour

Laura Ramoso is scheduled to perform in Chicago on Friday, September 25, 2026, as part of her “The Calm Down Tour”.

Friday, September 25th
7:30 p.m. – 9:30 p.m.
The Chicago Theatre
175 N. State Street, Chicago, IL 60601
Michael Shannon & Jason Narducy
Sep25
Music & Comedy

Michael Shannon & Jason Narducy

Michael Shannon & Jason Narducy will perform live at Riviera Theatre on Sep. 25, 2026.

Friday, September 25th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Whipped Cream – Home Was Always Me Tour
Sep25
Music & Comedy

Whipped Cream – Home Was Always Me Tour

Whipped Cream is scheduled to perform live in Chicago, Illinois on Friday, September 25, 2026, as part of her Home Was Always Me Tour.

Friday, September 25th
7:30 p.m. – 10:30 p.m.
Park West
1901 W. Madison Street, Chicago
Best of the Second City
Sep25
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…

Friday, September 25th
8:00 p.m. – 9:30 p.m.
The Second City
1616 N. Wells St.
The Cosmic Underground Show
Sep25
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…

Friday, September 25th
8:00 p.m. – 9:30 p.m.
cosmic underground theater
3433 W Fullerton Ave
Martin Lawrence – Y’all Still Know What It Is! Tour
Sep25
Music & Comedy

Martin Lawrence – Y’all Still Know What It Is! Tour

Legendary comedian and actor Martin Lawrence will perform live in Chicago on Friday, September 25, 2026, at 8:00 PM.

Friday, September 25th
8:00 p.m. – 10:00 p.m.
Arie Crown Theater
2301 S. Jean Baptiste Point DuSable, S Lake Shore Dr
Paula Cole – THIS FIRE: 30
Sep25
Music & Comedy

Paula Cole – THIS FIRE: 30

Paula Cole is bringing her “THIS FIRE: 30” anniversary tour to Chicago in late 2026 to celebrate the 30th anniversary of her breakthrough album.

Friday, September 25th
8:00 p.m. – 11:00 p.m.
Thalia Hall
main stage is located at 2550 N. Lincoln Ave., Chicago, IL 60614
Matute – Stereo Tour
Sep25
Music & Comedy

Matute – Stereo Tour

Matute is bringing their Stereo Tour to the Rosemont Theatre on Friday, September 25, 2026, at 8:00 PM.

Friday, September 25th
8:00 p.m. – 11:00 p.m.
Rosemont Theatre
Saint Levant – Chicago – Afandi World Tour
Sep25
Music & Comedy

Saint Levant – Chicago – Afandi World Tour

Palestinian-Algerian-Serbian artist Saint Levant is bringing his Afandi World Tour to Chicago for a two-night run on Thursday, September 24 and Friday, September 25, 2026.

Friday, September 25th
8:00 p.m. – 11:00 p.m.
Reggaeton Y2K
Sep25
Music & Comedy

Reggaeton Y2K

The high-energy throwback party Reggaetón Y2K is coming to Chicago, Illinois on Friday, September 25, 2026. This dance party celebrates the golden era of old-school…

Friday, September 25th
9:00 p.m. – 11:30 p.m.