Things to do in Chicago Loop
53 upcoming events in Chicago Loop, Chicago.
Thursday, Oct 1
BROTHER JOHN – Host The Jam
Buddy Guy's Legends
Enjoy an open mic jam hosted by Brother John with live music at Buddy Guy's Legends. Perfect for music lovers and aspiring performers.
Thursday, Oct 1
JIMMY BURNS – Host The Jam
Buddy Guy's Legends
Join us for an open mic jam hosted by Jimmy Burns. Perfect for music lovers and aspiring performers.
Friday, Oct 2
Insecure: The 10th Anniversary Tour
The Chicago Theatre
Join Issa Rae for Insecure: The 10th Anniversary Tour at The Chicago Theatre. A special event for fans of the series.
Friday, Oct 2
SONIC SOUL
Buddy Guy's Legends
Join SONIC SOUL for an electrifying night of music at Buddy Guy's Legends. Perfect for jazz and blues enthusiasts.
Saturday, Oct 3
Bill Burr Live
The Chicago Theatre
Enjoy a night of comedy with Bill Burr at The Chicago Theatre. Ideal for fans of stand-up and live performances.
Saturday, Oct 3
LIL ED
Buddy Guy's Legends
Join LIL ED for a night of electrifying music at Buddy Guy's Legends. Perfect for blues and jazz fans.
Saturday, Oct 3
JaxxSway - October 3, 2026
ROOF on theWit
Join JaxxSway for an electrifying night of music and dancing at ROOF on theWit. Ideal for nightlife lovers.
Sunday, Oct 4
Bill Burr Live
The Chicago Theatre
Catch comedian Bill Burr performing live at The Chicago Theatre on select dates. A must-see for comedy fans.
Sunday, Oct 4
CURTIS SALGADO
Buddy Guy's Legends
Experience blues legend Curtis Salgado live at Buddy Guy's Legends. A must-see for blues enthusiasts and music fans.
Sunday, Oct 4
Bill Burr Live
The Chicago Theatre
Catch Bill Burr performing at The Chicago Theatre. A must-see for comedy lovers looking for a night of laughter.
Monday, Oct 5
DAVE WELD
Buddy Guy's Legends
Experience an electrifying night with Dave Weld at Buddy Guy's Legends, featuring a free jazz set before the main event.
Thursday, Oct 8
Vibe Thursday - October 8, 2026
ROOF on theWit
Dance the night away with world-class DJs at ROOF on theWit. A vibrant nightlife experience in Chicago.
Friday, Oct 9
Souvenirs: 80 Years of John Prine
The Chicago Theatre
Celebrate the legacy of John Prine with a tribute concert at The Chicago Theatre. A must for his fans.
Friday, Oct 9
JW JONES
Buddy Guy's Legends
Experience an electrifying night with JW JONES at Buddy Guy's Legends. Great for blues enthusiasts and music lovers.
Friday, Oct 9
Kite - October 9, 2026
ROOF on theWit
Join us for an electrifying night of music and dancing at Kite at ROOF on theWit. Great for nightlife enthusiasts.
Saturday, Oct 10
Jerry Seinfeld
The Chicago Theatre
See Jerry Seinfeld perform live at The Chicago Theatre. A great event for comedy lovers.
Saturday, Oct 10
WILL TILLON
Buddy Guy's Legends
Enjoy a night of live music featuring Will Tillon and the Donna Herula Trio. Great for fans of jazz and blues.
Saturday, Oct 10
Jerry Seinfeld
The Chicago Theatre
See Jerry Seinfeld perform live at The Chicago Theatre for a night of comedy. A must-see for fans of stand-up.
Sunday, Oct 11
DEMETRIA TAYLOR
Buddy Guy's Legends
Join Demetria Taylor for a night of blues at Buddy Guy's Legends in Chicago. Great for blues music lovers looking for live performances.
Monday, Oct 12
LUKE PYTEL
Buddy Guy's Legends
Join headliner Luke Pytel for a night of live music, along with a free jazz set before the show. A great night for music lovers.
Friday, Oct 16
ROCKY ATHAS
Buddy Guy's Legends
Experience an electrifying performance by Rocky Athas at Buddy Guy's Legends. Ideal for blues music lovers.
Saturday, Oct 17
Brad Williams
The Chicago Theatre
See Brad Williams bring his Tall Tales Tour to The Chicago Theatre. A great night for comedy fans.
Saturday, Oct 17
MAHINDRA BLUES FEST – JENI GROUWS
Buddy Guy's Legends
Join the Mahindra Blues Fest at Buddy Guy's Legends in Chicago featuring Jeni Grouws. A must for blues music lovers.
Sunday, Oct 18
MAHINDRA BLUES FEST – NEW ORLEANS BEAU
Buddy Guy's Legends
Join us for an exciting night of blues music at Buddy Guy's Legends. A must for blues enthusiasts.
Monday, Oct 19
ELEVATION BAND – LITTLE WALTER FOUNDATION
Buddy Guy's Legends
Join the Elevation Band for a lively performance supporting the Little Walter Foundation. Great for blues and jazz lovers.
Friday, Oct 23
LIZ MANDEVILLE
Buddy Guy's Legends
Enjoy a night of live music featuring Liz Mandeville and an acoustic set by Matt Hendricks. Perfect for blues and jazz fans.
Saturday, Oct 24
RAY FULLER
Buddy Guy's Legends
Enjoy live music from Ray Fuller at Buddy Guy's Legends. A great night for blues and jazz fans.
Sunday, Oct 25
COREY DENNISON
Buddy Guy's Legends
Enjoy a night of jazz and blues with Corey Dennison at Buddy Guy's Legends. A vibrant evening for music lovers in Chicago.
Monday, Oct 26
Brett Goldstein
The Chicago Theatre
See Brett Goldstein's Sex, Death & Small Talk Tour at The Chicago Theatre. A must for comedy fans.
Tuesday, Oct 27
An Evening with Tedeschi Trucks Band
The Chicago Theatre
Experience the Future Soul Tour with Tedeschi Trucks Band at The Chicago Theatre. A must-see for live music fans.
Showing 1–30 of 53 upcoming events.
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