Things to do in Chicago

Saturday, Oct 17

Luke Pytel Band: Celebrating Luke’s B-Day

Rosa's Lounge

Celebrate Luke's birthday with the Luke Pytel Band at Rosa's Lounge. A night of blues and special guest performances awaits.

Saturday, Oct 17

Claudia's 5K

Boulevard

Participate in Claudia's 5K to support mental health awareness. A meaningful run promoting courage and community connection.

Saturday, Oct 17

Vintage on the Avenue

The Shops at North Bridge

Explore a curated collection of high-end vintage clothing and accessories at this unique shopping event.

Saturday, Oct 17

SATURDAY OCTOBER 17: COMEDY BRUNCH! FEATURING BAD MOMZ OF COMEDY

The Comedy Bar

Enjoy a hilarious brunch with Orly K.G.'s Bad Momz of Comedy at The Comedy Bar. A fun event full of stand-up and laughs.

Saturday, Oct 17

High School Ensemble Show

UP Comedy Club

Watch talented students perform in sketch, improv, and stand-up at The Second City. A fun outing for comedy fans.

Saturday, Oct 17

Josh Ocean Thomas

The Lincoln Lodge

Enjoy an evening of stand-up comedy with Josh Ocean Thomas in Chicago. A great night for comedy fans looking for laughs.

Saturday, Oct 17

Chicago Fire FC at New England Revolution

Fatpour McCormick: Ultimate Chicago Sports Bar

Watch the Chicago Fire face off against New England Revolution at Fatpour. A great spot for sports fans.

Sunday, Oct 18

Club Crib

The California Clipper

Experience RnB, Soul, and Jazz at Club Crib with talented musicians at The California Clipper. Ideal for music lovers and night owls.

Sunday, Oct 18

SATURDAY OCTOBER 17: JOEY BRAGG

The Comedy Bar

Join comedian Joey Bragg for a night of laughs at The Comedy Bar. Enjoy a fun atmosphere right off the Magnificent Mile.

Sunday, Oct 18

“Ask a Comedian” Comedy Show w/ Kyrie Da Comic

The Lincoln Lodge

Experience the unique comedy show at The Lincoln Lodge in Chicago. Perfect for comedy enthusiasts.

Sunday, Oct 18

Tatum Langley featuring Jeremy Kahn Quartet

Winter's Jazz Club

Enjoy a night of jazz with Tatum Langley and the Jeremy Kahn Quartet at Winter's Jazz Club. Perfect for jazz enthusiasts.

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.

Sunday, Oct 18

HOP LATE NIGHT TIL 5AM with DJ Eves + JuJu

Hopsmith Chicago

Dance with DJ Eves and JuJu at Hopsmith Chicago for an unforgettable late-night experience.

Sunday, Oct 18

SATURDAY OCTOBER 17: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Enjoy a night of stand-up comedy featuring Chicago's best comedians at The Comedy Bar. Perfect for a fun night out.

Sunday, Oct 18

Joe Wortell

Broken Hearts

Experience heartfelt country music with Joe Wortell at Broken Hearts, featuring engaging stories and catchy tunes.

Sunday, Oct 18

Rick King's Royal Hustle

Rosa's Lounge

Join us for Rick King's Royal Hustle at Rosa's Lounge. A lively night of blues music and entertainment.

Sunday, Oct 18

DELIRIUM: Danse Macabre

The Newport Theater

Experience an artsy event curated by Willy LaQueue at The Newport Theater. Ideal for those interested in unique cultural experiences.

Sunday, Oct 18

Josh Ocean Thomas

The Lincoln Lodge

Enjoy an evening of stand-up comedy with Josh Ocean Thomas, a Chicago-based comedian. Perfect for comedy lovers.

Sunday, Oct 18

Y.u.kiko, Nosha Luv, Raven Wright

The California Clipper

Enjoy a night of Soul, RnB, Disco, and Funk with Y.u.kiko and others at The California Clipper. Great for music lovers.

Sunday, Oct 18

Rick King's Royal Hustle

Rosa's Lounge

Join us for a late-night blues set with Rick King's Royal Hustle at Rosa's Lounge. Ideal for blues fans.

Sunday, Oct 18

Vintage on the Avenue

The Shops at North Bridge

Explore high-end vintage clothing and accessories at The Shops at North Bridge. A unique shopping experience for vintage lovers.

Sunday, Oct 18

Clued In Presents: Travel Can Be Murder

The Second City Training Center

Experience an improvised murder mystery inspired by Agatha Christie at The Second City. Perfect for mystery fans and comedy lovers.

Sunday, Oct 18

Clued In Presents: Travel Can Be Murder

UP Comedy Club

Enjoy a unique improvised murder mystery experience at UP Comedy Club. Ideal for fans of comedy and suspense.

Sunday, Oct 18

Clued In Presents: Travel Can Be Murder

The Second City

Experience an improvised murder mystery at The Second City. Perfect for fans of comedy and interactive theater.

Sunday, Oct 18

An Evening with Danny Sinoff and the Great American Songbook - Debut!

Winter's Jazz Club

Enjoy a night of jazz with Danny Sinoff and his band, perfect for jazz lovers and music enthusiasts.

Sunday, Oct 18

Saya Meads

The Lincoln Lodge

Comedian Saya Meads performs standup at The Lincoln Lodge, promising a night of laughter and entertainment.

Sunday, Oct 18

FALL BREAK | Comedy Showcase

RED ROOM Comedy Club

Enjoy a night of laughter at the FALL BREAK Comedy Showcase featuring up-and-coming comedians at RED ROOM Comedy Club.

Sunday, Oct 18

Seattle Reign FC at Chicago Stars FC

Fatpour McCormick: Ultimate Chicago Sports Bar

Watch the Seattle Reign FC take on the Chicago Stars FC at Fatpour Tap Works. Perfect for soccer fans.

Monday, Oct 19

Sautéed Standup: Chicago's Only Live Comedy Cooking Competition Show!

The Lincoln Lodge

Enjoy a unique live comedy cooking competition at The Lincoln Lodge. Great for foodies and comedy lovers alike.

Monday, Oct 19

SUNDAY OCTOBER 18: CALIMAR WHITE

The Comedy Bar

Enjoy a night of laughs with Calimar White at The Comedy Bar. A fun comedy event with pizza and nonstop humor.