Things to do in Chicago

Sunday, Oct 11

Dave Herrero Featuring Pete Galanis

Rosa's Lounge

Experience a night of blues with Dave Herrero and Pete Galanis. Ideal for blues music lovers.

Sunday, Oct 11

olivia rodrigo at united center

Kaiser Tiger

Experience Olivia Rodrigo live with a complimentary shuttle service to the United Center. A must-see for pop music fans.

Sunday, Oct 11

Paul Marinaro Quintet - The Music of Nat 'King' Cole

Winter's Jazz Club

Enjoy the music of Nat 'King' Cole performed by Paul Marinaro and his quintet. Perfect for jazz lovers.

Sunday, Oct 11

Mike Falzone - one night only

The Lincoln Lodge

Enjoy a night of hilarious standup comedy with Mike Falzone at The Lincoln Lodge. Perfect for comedy fans in Chicago.

Sunday, Oct 11

SUNDAY OCTOBER 11: TIM SHROPSHIRE

The Comedy Bar

Join headliner Tim Shropshire for a night of laughs at The Comedy Bar in Chicago. A must-see for comedy enthusiasts.

Monday, Oct 12

The Scovilles

Broken Hearts

Catch The Scovilles for a night of electrifying Rock and Roll at Broken Hearts. A must-see for rock fans.

Monday, Oct 12

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Redhead Piano Bar

Join us for a night of entertainment at Redhead Piano Bar. A lively venue for music lovers.

Monday, Oct 12

SUNDAY OCTOBER 11: BARRY BREWER

The Comedy Bar

Headliner Barry Brewer brings laughs to The Comedy Bar in Chicago. A great choice for comedy fans looking for a fun night.

Monday, Oct 12

The Metalliques - Live

Skylark

Enjoy a free live performance by The Metalliques at Skylark in Chicago. A vibrant night for music lovers.

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.

Monday, Oct 12

olivia rodrigo at united center (Copy)

Kaiser Tiger

Enjoy a complimentary shuttle service to the United Center for Olivia Rodrigo's concert from Kaiser Tiger.

Tuesday, Oct 13

MONDAY OCTOBER 12: LATE NITE MIC WITH VIK PANDYA

The Comedy Bar

Join Vik Pandya and special guests for a night of comedy at The Comedy Bar in Chicago. Perfect for comedy lovers.

Tuesday, Oct 13

1st Set With Henry Johnson %26 Charles %26#8216;Rick’ Heath

Andy's Jazz Club & Restaurant

Experience live jazz with Henry Johnson and Charles 'Rick' Heath at Andy's Jazz Club & Restaurant.

Tuesday, Oct 13

October Member Meeting

CHAOS Brew Club

Meet club members and tour the brewhouse at the October Member Meeting. An inviting event for beer enthusiasts.

Wednesday, Oct 14

TUESDAY OCTOBER 13: TOMATO THROW SHOW

The Comedy Bar

Participate in an interactive comedy show at The Comedy Bar in Chicago. A unique night for comedy fans.

Wednesday, Oct 14

House of Improv

UP Comedy Club

Enjoy a showcase of exciting improv teams at House of Improv for a night filled with laughter.

Wednesday, Oct 14

WIGS: A standup comedy show

The Lincoln Lodge

Enjoy a unique stand-up comedy show in wigs at The Lincoln Lodge. Perfect for fans of quirky comedy.

Wednesday, Oct 14

Grad Revue Preview

UP Comedy Club

Catch the Grad Revue Preview at UP Comedy Club for a night of laughs. A fun event for comedy fans in Chicago.

Wednesday, Oct 14

Best Night Ever

The Lincoln Lodge

Enjoy a night of laughs at one of Chicago's top comedy showcases. Ideal for comedy lovers looking for a fun Tuesday night.

Wednesday, Oct 14

Notes on Masculinity

The California Clipper

Join a bi-monthly performance of Notes on Masculinity featuring drag and burlesque artists in Chicago.

Wednesday, Oct 14

Jen Porter

Redhead Piano Bar

Experience captivating performances by Jen Porter in a lively atmosphere. Perfect for a late-night outing with friends.

Wednesday, Oct 14

smashing pumpkins at united center

Kaiser Tiger

Catch the Smashing Pumpkins live at the United Center. A great event for rock music enthusiasts.

Wednesday, Oct 14

Michael Lerich Quartet - Swingin’ the Great American Songbook

Winter's Jazz Club

Experience the Michael Lerich Quartet performing the Great American Songbook at Winter's Jazz Club. Ideal for jazz enthusiasts.

Thursday, Oct 15

October Bingo Night

ERIS Brewery and Cider House

Join us for October Bingo Night at Eris Brewery. A fun evening for friends and bingo lovers alike.

Thursday, Oct 15

WEDNESDAY OCTOBER 14: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Laugh the night away with Chicago's best comedians at The Comedy Bar. Enjoy pizza and great company in a lively atmosphere.

Thursday, Oct 15

Chicago Fire FC vs. Philadelphia Union

Fatpour McCormick: Ultimate Chicago Sports Bar

Catch the Chicago Fire FC take on the Philadelphia Union at Soldier Field, with pregame at Fatpour McCormick.

Thursday, Oct 15

Lil Weenieprov

The Lincoln Lodge

Enjoy Lil Weenieprov at The Lincoln Lodge for a night of improv comedy. Perfect for fans of laughter and live performances.

Thursday, Oct 15

The Foxhounds

Broken Hearts

Enjoy a lively evening of bluegrass music with The Foxhounds at Broken Hearts. A treat for music lovers.

Thursday, Oct 15

2026 Sam Adams Stein Hoisting Contest!

Timothy O'Toole's Pub Chicago

Join the fun at the Sam Adams Stein Hoisting Contest at Timothy O'Toole's Pub. Compete for prizes in a spirited atmosphere.

Thursday, Oct 15

blackhawks at united center

Kaiser Tiger

Watch the Blackhawks play at United Center with a complimentary shuttle service. Perfect for sports fans looking for a convenient game night.