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Upcoming Chicago Events

Check out what's happening all around Chicago.

October 2, 2026: Oct2
Music & Comedy
Dauod Naimyar at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Dauood Naimyar taped a Comedy Central…
River North
Event details
Friday, October 2nd
7:00 p.m. – 8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Oct2
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
Friday, October 2nd
7:30 p.m. – 8:55 p.m.
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Apollo Theater
2550 N. Lincoln Ave.
Oct2
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…
Lincoln Park
Event details
Friday, October 2nd
7:30 p.m. – 9:00 p.m.
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iO Theater
1501 N. Kingsbury St.
Oct2
Music & Comedy
MrBallen: Lights Out Live
MrBallen is scheduled to bring his “Lights Out Live” show to Chicago on Friday, October 2, 2026.
Loop
Event details
Friday, October 2nd
7:30 p.m. – 9:30 p.m.
The Chicago Theatre
175 N. State Street, Chicago, IL 60601
Oct2
Music & Comedy
Bill Burr Live Tour 2026
Bill Burr is performing live in Chicago on Friday, October 2, 2026, as part of his newly announced stand-up tour.
Loop
Event details
Friday, October 2nd
7:30 p.m. – 9:30 p.m.
The Chicago Theatre
175 N. State Street, Chicago, IL 60601
Oct2
Music & Comedy
VOCES8
The British vocal octet VOCES8, described as a “purring musical machine” by The Arts Desk, is equally at home with the intricate polyphony of Bach, the…
Event details
Friday, October 2nd
7:30 p.m. – 9:30 p.m.
Rockefeller Memorial Chapel
5850 S Woodlawn Ave
Oct2
Music & Comedy
DJ Shadow – Endtroducing 30th Anniversary Tour
DJ Shadow is performing at The Vic Theatre in Chicago on Friday, October 2, 2026. The show is part of his “Endtroducing 30th Anniversary Tour,”…
Event details
Friday, October 2nd
7:30 p.m. – 10:30 p.m.
The Vic Theatre
3145 N. Sheffield
Oct2
Music & Comedy
LE SSERAFIM – PUREFLOW Tour
LE SSERAFIM is bringing their newly announced “PUREFLOW Tour” to the United Center in Chicago on Friday, October 2, 2026.
West Loop
Event details
Friday, October 2nd
7:30 p.m. – 10:30 p.m.
United Center
1901 W Madison St,
Oct2
Music & Comedy
Isaiah Falls: LVRS Paradise – Side B Tour
Isaiah Falls will bring his LVRS Paradise – Side B Tour to Chicago, Illinois, on Friday, October 2, 2026, performing live at Park West. The…
Event details
Friday, October 2nd
7:30 p.m. – 10:30 p.m.
Park West
1901 W. Madison Street, Chicago
Oct2
Music & Comedy
Ripe – Chicago, IL – Play the Game Fall Tour
Alternative pop-funk band Ripe will perform live at Thalia Hall in Chicago on Friday, October 2, 2026. The concert is a stop on their Play…
Pilsen
Event details
Friday, October 2nd
7:30 p.m. – 10:30 p.m.
Thalia Hall
1807 S Allport St, Chicago, IL 60608
Oct2
Music & Comedy
Mastodon – The Poisonous Weapons Tour
Mastodon is performing live in Chicago on Friday, October 2, 2026, headlining a massive heavy music lineup on “The Poisonous Weapons Tour”. Supporting Lineup: This…
Uptown
Event details
Friday, October 2nd
7:30 p.m. – 11:00 p.m.
The Riveria Theater
4746 N Racine Ave
Oct2
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
Friday, October 2nd
8:00 p.m. – 9:15 p.m.
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The Den Theatre
1331 North Milwaukee Avenue
Oct2
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
Friday, October 2nd
8:00 p.m. – 9:30 p.m.
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The Second City
1616 N. Wells St.
Oct2
Music & Comedy, Theatre & Performing Arts
Freedom Riders with special guests Kurt Elling & Lizz Wright
In the 1960s, Freedom Rider activists challenged racial segregation in the Southern United States. With reverence for their courage and struggle, this groundbreaking international jazz…
Loop
Event details
Friday, October 2nd
8:00 p.m. – 10:00 p.m.

220 S. Michigan Ave.
Oct2
Music & Comedy
Chicago’s Best Comedy Show at The Comedy Bar
IMPORTANT HOUSE POLICIES: PLEASE READ 📍 All shows take place at 162 E Superior St. – The entrance to the venue is on Superior Street,…
River North
Event details
Friday, October 2nd
9:00 p.m. – 10:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611
Oct2
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
Friday, October 2nd
9:30 p.m. – 11:00 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct2
Music & Comedy
Kohl’s Cash: TGIF (That’s Good Improv Friday)
Start your weekend off laughing at one of the hottest improv shows in Chicago! Every Friday at 9:30pm, iO house team Kohl’s Cash presents a…
Lincoln Park
Event details
Friday, October 2nd
9:30 p.m. – 11:00 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Oct2
Oct3
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
Friday, October 2nd
11:00 p.m. – Saturday, October 3rd
12:00 a.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
October 3, 2026: Oct3
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 3rd
3:00 p.m. – 4:30 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct3
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 3rd
6:00 p.m. – 7:00 p.m.
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de Maat Theatre at Second City
230 W North Ave
Oct3
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 3rd
6:00 p.m. – 7:30 p.m.
See all events in series
iO Theater
1501 N. Kingsbury St.
Oct3
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 3rd
6:30 p.m. – 8:00 p.m.
See all events in series
The Second City
1616 N. Wells St.
Oct3
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 3rd
7:00 p.m. – 8:00 p.m.
See all events in series
The Second City
230 W North Ave., 2nd Floor
Oct3
Music & Comedy
Dauood Naimyar at The Comedy Bar
2-Item Minimum Per Guest Valid ID Required for Entry First Come, First Served Seating No Outside Food or Beverage Dauood Naimyar taped a Comedy Central…
River North
Event details
Saturday, October 3rd
7:00 p.m. – 8:30 p.m.
The Comedy Bar
162 E Superior St, Chicago, IL 60611

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