Things to do in Chicago Loop

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.

Thursday, Oct 29

Father Mike Schmitz

The Chicago Theatre

See Father Mike Schmitz for Parables: A Time of Reflection at The Chicago Theatre. Ideal for those interested in inspirational talks.

Thursday, Oct 29

From Lava to Vine: A Volcanic Wine Dinner

The Village

Explore volcanic wines with a curated dinner at The Village. Perfect for wine enthusiasts and food lovers.

Friday, Oct 30

NIGEL MACK

Buddy Guy's Legends

Experience an electrifying performance by Nigel Mack at Buddy Guy's Legends. A great night for live music enthusiasts.

Saturday, Oct 31

Don Lemon & DL Hughley: DL + DL 'Anything Goes'

The Chicago Theatre

See Don Lemon and DL Hughley perform their comedy show at The Chicago Theatre. Perfect for comedy fans looking for a night of laughs.

Saturday, Oct 31

BLUES PEOPLE

Buddy Guy's Legends

Enjoy an electrifying night of blues with BLUES PEOPLE at Buddy Guy's Legends in Chicago. Perfect for live music fans.

Sunday, Nov 1

The Rocky Horror Picture Show

The Chicago Theatre

See The Rocky Horror Picture Show at The Chicago Theatre for a spooktacular night. Perfect for fans of cult classic cinema.

Thursday, Nov 5

Blade Runner Live

The Chicago Theatre

See Blade Runner Live with a live score at The Chicago Theatre, perfect for film and music lovers.

Friday, Nov 6

312 Comedy Festival® Presents Joey Diaz

The Chicago Theatre

Catch Joey Diaz at the 312 Comedy Festival, bringing laughs to The Chicago Theatre this November.

Sunday, Nov 8

SkyRise Chicago 2026

Catalog at Willis Tower

Join the annual SkyRise Chicago Stair Climb at Willis Tower. Great for fitness enthusiasts and supporters of Shirley Ryan AbilityLab.

Friday, Nov 27

Thanksgiving Feast for 10 People at Home

Fairmont Chicago, Millennium Park

Enjoy a luxurious Thanksgiving feast prepared by our culinary team. Perfect for families celebrating the holiday at home.

Saturday, Nov 28

GRAMMY AWARD WINNING BOBBY RUSH

Buddy Guy's Legends

Experience an electrifying night with Grammy-winning Bobby Rush in Chicago. A must for blues and jazz fans.

Saturday, Dec 5

Wilco

The Chicago Theatre

Catch Wilco's Winterlude at The Chicago Theatre for a night of live rock music. Ideal for fans of the band and live performances.

Saturday, Feb 20

Aries Spears

The Chicago Theatre

See Aries Spears perform live at The Chicago Theatre. A great night out for comedy fans.

Saturday, Feb 27

Professor Brian Cox

The Chicago Theatre

See Professor Brian Cox on his Emergence Worldwide Tour. A fascinating event for science and education enthusiasts.

Monday, Mar 1

Twilight In Concert

The Chicago Theatre

Enjoy Twilight in Concert at The Chicago Theatre, a unique musical experience for fans of the beloved film series.

Sunday, Mar 14

The Basement Yard

The Chicago Theatre

See The Basement Yard live at The Chicago Theatre. A fun event for comedy and entertainment lovers.

Saturday, Mar 20

Ali Wong Live

The Chicago Theatre

Catch Ali Wong performing live at The Chicago Theatre. A must-see for comedy fans.