Things to do in Chicago

Friday, Dec 18

Judah Friedlander Live In Chicago

The Lincoln Lodge

Join Judah Friedlander for an all-new stand-up performance at The Lincoln Lodge. Ideal for comedy lovers.

Friday, Dec 18

Cash Box Kings feat. Cameron Webb

Rosa's Lounge

Join Cash Box Kings for a blues night at Rosa's Lounge. A great event for blues enthusiasts.

Saturday, Dec 19

High School Ensemble Show

UP Comedy Club

Watch talented students showcase their skills in comedy. A delightful afternoon for families and comedy fans alike.

Saturday, Dec 19

GRACE BAHLER LIVE! IN CHICAGO

The Lincoln Lodge

Experience an hour of elegant insanity with Grace Bahler's comedy show. A must-see for fans of unique humor.

Saturday, Dec 19

Graham Byrne is Back in Chicago and Performing A Brand New Hour

The Lincoln Lodge

Chicago native Graham Byrne returns home to perform his brand new standup hour. A must-see for comedy fans.

Saturday, Dec 19

SATURDAY DECEMBER 19: CHRISTIAN JOHNSON

The Comedy Bar

Join Christian Johnson for a night of comedy at The Comedy Bar in Chicago. A great event for laughter.

Saturday, Dec 19

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

The Lincoln Lodge

Join Kyrie Da Comic for an interactive comedy show at The Lincoln Lodge. A fun night for comedy fans looking for a unique experience.

Saturday, Dec 19

Judah Friedlander Live In Chicago

The Lincoln Lodge

Judah Friedlander brings all-new stand-up to The Lincoln Lodge. A unique experience for comedy lovers.

Saturday, Dec 19

SATURDAY DECEMBER 19: CHRISTIAN JOHNSON

The Comedy Bar

Experience a night of laughs with Christian Johnson at The Comedy Bar in Chicago. Ideal for comedy lovers.

Saturday, Dec 19

Ivan Singh Band: Lata-de-Batata Blues

Rosa's Lounge

Join the Ivan Singh Band for a late-night blues set with special guests. A relaxed atmosphere for blues lovers.

Saturday, Dec 19

AFROBEATS SATURDAYZ @ MASADA: Detty December Edition

Masada Nightclub

Join the #1 Afrobeats dance party in Chicago. Perfect for those who love vibrant music and energetic dancing.

Saturday, Dec 19

Ivan Singh Band: Lata-de-Batata Blues

Rosa's Lounge

Join the Ivan Singh Band for a late-night blues set with special guests. A relaxed atmosphere for blues lovers.

Sunday, Dec 20

A Brunch of Drag

Simone's

Join us for a spooktacular Brunch of Drag at Simone's. Enjoy a lively atmosphere and great entertainment.

Sunday, Dec 20

Show & Tell for Grown-Ups: Monthly Showcase of Audience Favorites!

The Lincoln Lodge

Enjoy a showcase of audience favorite presentations at The Lincoln Lodge. A fun event for those who love sharing and learning.

Sunday, Dec 20

Myq Kaplan Does the Best Stand-Up Comedy You've Never Seen!

The Lincoln Lodge

Experience stand-up comedy with Myq Kaplan at The Lincoln Lodge. A great night for comedy enthusiasts.

Sunday, Dec 20

Guitar For Guaraldi - Live

Skylark

Join us for a live tribute to Vince Guaraldi at Skylark, featuring music from the Peanuts specials. A festive evening for music lovers.

Sunday, Dec 20

MIKE DANGEROUX

Buddy Guy's Legends

Enjoy a night of live music with Mike Dangeroux at Buddy Guy's Legends. Perfect for jazz and blues fans.

Sunday, Dec 20

Jen Porter

Redhead Piano Bar

Enjoy a captivating performance by Jen Porter at The Redhead Piano Bar. A perfect late-night outing for music lovers in Chicago.

Monday, Dec 21

Welcome to the Show *FREE*

The Getaway

Enjoy karaoke night hosted by JK in a fun and lively atmosphere.

Tuesday, Dec 22

Trauma Dumping: A Hilarious Comedy Show!

The Lincoln Lodge

Laugh along with Chicago's best comedians sharing their worst experiences. A must-see for comedy fans.

Tuesday, Dec 22

TBOYSKR1PCLUB

The Newport Theater

Join the pop-up skrip club and rent party at The Newport Theater for a night of community and fun. Perfect for local art lovers.

Tuesday, Dec 22

Pro Wrestling Tees presents: ALL ELITE COMEDY Live in Chicago!

The Lincoln Lodge

Join comedians from the wrestling world for a night of laughs at The Lincoln Lodge. Perfect for wrestling fans and comedy lovers.

Wednesday, Dec 23

Rosa’s All-Star Band Feat. Lil’ Ed Williams & Sumito “Ariyo” Ariyoshi

Rosa's Lounge

Enjoy a night with Rosa’s All-Star Band featuring Lil’ Ed Williams at Rosa's Lounge. A lively blues performance awaits.

Wednesday, Dec 23

Rosa’s All-Star Band Feat. Lil’ Ed Williams & Sumito “Ariyo” Ariyoshi

Rosa's Lounge

Enjoy a night with Rosa’s All-Star Band featuring Lil’ Ed Williams at Rosa's Lounge. A lively blues performance awaits.

Thursday, Dec 24

Christmas Eve

Lush Wine & Spirits - Roscoe Village

Celebrate Christmas Eve at Lush Wine & Spirits. Enjoy festive drinks and a warm atmosphere with friends.

Thursday, Dec 24

Happy Holidays!

Redhead Piano Bar

Celebrate the holiday season with live performances at The Redhead Piano Bar. A festive atmosphere perfect for enjoying music and drinks.

Thursday, Dec 24

Seasons Greetings! We are closed!

Rosa's Lounge

Rosa's Lounge will be closed for the holiday season. Please check back for updates.

Friday, Dec 25

Christmas Day

Lush Wine & Spirits - Roscoe Village

Celebrate Christmas Day at Lush Wine & Spirits. Enjoy festive drinks and a warm atmosphere with friends.

Friday, Dec 25

Christmas

Thai 55 Restaurant

Join us for a festive Christmas celebration at Thai 55 with family and friends. Enjoy delicious holiday meals.

Friday, Dec 25

XMAS FRIDAY @ MASADA: Afrobeats, Amapiano, Dancehall, RnB

Masada Nightclub

Join us for the #1 Afrobeats dance party at Masada Nightclub on December 26, 2026. Enjoy a night of music and dancing.