Upcoming Chicago Events

Name: Best of Chicago Comedy – Chicago
Start: 2026-10-01T00:00:00-05:00
End: 2026-10-01T23:59:59-05:00
Location: The Foundation Room at House Of Blues – Chicago

Check out what's happening all around Chicago.

September 28, 2026: Sep28
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, September 28th
7:00 p.m. – 8:30 p.m.
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iO Theater
1501 N. Kingsbury St.
Sep28
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, September 28th
7:00 p.m. – 8:30 p.m.
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The Second City
1616 N. Wells St.
Sep28
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…
Uptown
Event details
Monday, September 28th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Sep28
Music & Comedy
Sara Bareilles – Good Grief Tour
Sara Bareilles will perform live at The Chicago Theatre on September 27-28, 2026, as part of her newly announced “The Good Grief Tour”. The concert…
Loop
Event details
Monday, September 28th
8:00 p.m. – 11:00 p.m.
The Chicago Theatre
175 N. State Street, Chicago, IL 60601
Sep28
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, September 28th
9:00 p.m. – 10:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Sep28
Sep29
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, September 28th
11:00 p.m. – Tuesday, September 29th
12:00 a.m.
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iO Theater
1501 N. Kingsbury St.
September 29, 2026: Sep29
Music & Comedy
MICO – Running From A Feeling Tour
The pop-punk and alternative artist MICO is scheduled to perform live in Chicago, Illinois on Tuesday, September 29, 2026. The performance is part of his…
River North
Event details
Tuesday, September 29th
6:00 p.m. – 9:00 p.m.
House of Blues
Sep29
Music & Comedy
Tomato Throw Show at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Join us for the most fun…
River North
Event details
Tuesday, September 29th
7:00 p.m. – 8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Sep29
Music & Comedy
Laurie Anderson & Sexmob – Republic of Love
Laurie Anderson is scheduled to perform live in Chicago, Illinois on Tuesday, September 29, 2026, showcasing her newly announced multimedia production, Republic of Love. The…
Uptown
Event details
Tuesday, September 29th
7:30 p.m. – 10:30 p.m.
The Riveria Theater
4746 N Racine Ave
Sep29
Music & Comedy
DOMi & JD Beck – Chicago – WHO ASKED? US TOUR
Grammy-nominated avant-garde jazz duo DOMi & JD Beck are bringing their headlining “WHO ASKED? US TOUR” to Chicago, Illinois on Tuesday, September 29, 2026. The…
Event details
Tuesday, September 29th
7:30 p.m. – 10:30 p.m.
Park West
1901 W. Madison Street, Chicago
Sep29
Music & Comedy
Arlo Parks – Desire Tour
Arlo Parks is bringing her Desire Tour to Chicago on Tuesday, September 29, 2026, at the historic Thalia Hall. The tour follows the release of…
Pilsen
Event details
Tuesday, September 29th
8:00 p.m. – 11:00 p.m.
Thalia Hall
main stage is located at 2550 N. Lincoln Ave., Chicago, IL 60614
Sep29
Music & Comedy
Johnny Blue Skies & The Dark Clouds – Mutiny for the Masses 2026 Tour
Johnny Blue Skies (the pseudonym for Sturgill Simpson) and his band The Dark Clouds are scheduled to perform at the United Center in Chicago on…
West Loop
Event details
Tuesday, September 29th
8:00 p.m. – 11:00 p.m.
United Center
1901 W Madison St,
Sep29
Music & Comedy
Lambrini Girls – 2026 World Tour
Lambrini Girls are scheduled to perform at the Vic Theatre in Chicago on Tuesday, September 29, 2026. with special guests Big Special and Big Girl.
Event details
Tuesday, September 29th
8:00 p.m. – 11:00 p.m.
The Vic Theatre
3145 N. Sheffield
Sep29
Sep30
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
Tuesday, September 29th
11:00 p.m. – Wednesday, September 30th
12:00 a.m.
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iO Theater
1501 N. Kingsbury St.
September 30, 2026: Sep30
Music & Comedy
Respawn Improv with Blue.0
A weekly improv show hosted by Blue.0 and featuring a rotating cast of indie teams formed right here at The iO Theater! Each Wednesday at…
Lincoln Park
Event details
Wednesday, September 30th
6:00 p.m. – 7:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Sep30
Music & Comedy
Knocked Loose & Denzel Curry – Hive Mind Tour
Knocked Loose and Denzel Curry are performing a co-headlining concert in Chicago on Wednesday, September 30, 2026, as part of their massive “Hive Mind Tour”…
Event details
Wednesday, September 30th
6:00 p.m. – 11:00 p.m.
The Salt Shed
1357 N Elston
Sep30
Music & Comedy
Crowd Work Wednesday at The Comedy Bar
2-Item Minimum Per Guest First Come, First Served Seating No Outside Food or Beverage Valid ID Required at Entry Crowd Work Wednesday is a weekly…
River North
Event details
Wednesday, September 30th
7:00 p.m. – 8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Sep30
Music & Comedy
Steve Lacy – Chicago, IL – Oh yeah? Tour
Steve Lacy will perform live at the Byline Bank Aragon Ballroom in Chicago, Illinois, on Wednesday, September 30, 2026. The Grammy-winning R&B and neo-soul artist…
Uptown
Event details
Wednesday, September 30th
7:00 p.m. – 10:00 p.m.
Aragon Ballroom
1106 W. Lawrence Ave., Chicago, IL 60640
Sep30
Music & Comedy
Play Time
A showcase of 3 short plays by select writing teams and featuring a cast of iO Theater performers. It’s experimental, it’s follow-the-fun, it’s Play Time. Plays…
Lincoln Park
Event details
Wednesday, September 30th
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Sep30
Music & Comedy, Theatre & Performing Arts
Sir Thomas Madden Jr.
Then God created Sir Thomas Madden Jr. Averaging six feet, six-and-a-half inches, Sir Thomas Madden Jr. is Jeff Madden and Paul Thomas, an Atlanta-Chicago sketch…
Wicker Park / Bucktown
Event details
Wednesday, September 30th
8:00 p.m. – 9:15 p.m.
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The Den Theatre
1331 North Milwaukee Avenue
Sep30
Music & Comedy
WED Nite Comedy Showdown
Don’t Miss The Hottest New Show in Chitown! This show puts 2 teams of Comedians against each other with the Audience Deciding who’s funniest! This…
Event details
Wednesday, September 30th
9:00 p.m. – 11:00 p.m.
My Buddy’s
4416 N. Clark Street
Sep30
Music & Comedy
The Fizz Show
Join iO house team Fizz for Chicago’s most carbonated improv show. Wednesdays at 10 p.m., Fizz cracks open a high-octane, full-sugar set of one-night-only scenes,…
Lincoln Park
Event details
Wednesday, September 30th
10:00 p.m. – 11:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Sep30
Oct1
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
Wednesday, September 30th
11:00 p.m. – Thursday, October 1st
12:00 a.m.
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iO Theater
1501 N. Kingsbury St.
October 1, 2026: Oct1
Music & Comedy
Best of Chicago Comedy – Chicago
Get ready for a night filled with laughter and unforgettable moments at the “Best of Chicago Comedy – Chicago”! Join us at The Foundation Room…
Event details
Thursday, October 1st
The Foundation Room at House Of Blues – Chicago
329 N Dearborn St, Chicago,