Live Music in Chicago, IL

Wednesday, Dec 16

Rosa's Blues Jam hosted by David Levit (of Million Dollar Blues Band)

Rosa's Lounge

Enjoy a night of blues with David Levit at Rosa's Lounge. Perfect for blues music fans.

Wednesday, Dec 16

Rosa's Blues Jam hosted by David Levit (of Million Dollar Blues Band)

Rosa's Lounge

Join David Levit for a late-night blues jam at Rosa's Lounge. A great night for music lovers.

Thursday, Dec 17

LeRoy Bach & Dan Bitney

The California Clipper

Experience an immersive evening with LeRoy Bach and Dan Bitney. Ideal for fans of experimental and jazz music.

Thursday, Dec 17

Live Music w/Irene Phillips

Nabala Cafe

Join us for an evening of live music with Irene Phillips. A cozy atmosphere for music lovers in Uptown.

Thursday, Dec 17

MANDALYN & THE HUNTERS

Buddy Guy's Legends

Experience live music with Mandalyn & The Hunters at Buddy Guy's Legends. Perfect for music lovers and night out.

Friday, Dec 18

Boogie Wonderland at Howl at the Moon

Howl at the Moon Chicago

Join the high-energy Boogie Wonderland event at Howl at the Moon. Perfect for fans of live music and disco vibes.

Friday, Dec 18

Boogie Wonderland (Chicago)

Howl at the Moon Chicago

Enjoy disco era throwback music and drink features at Howl at the Moon in Chicago. A fun night for lovers of retro music and cocktails.

Friday, Dec 18

YOUNG REIL

Buddy Guy's Legends

Enjoy an exciting night with YOUNG REIL and an acoustic set at Buddy Guy's Legends. Ideal for jazz and blues enthusiasts.

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.

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

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

Joey J Saye

The California Clipper

Enjoy a Sunday series spotlighting local independent artists across various genres in a cozy setting.

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

Live Music w/Minority Exchange

Nabala Cafe

Enjoy an evening of live music with Minority Exchange in a welcoming cafe atmosphere.

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

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.

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.

Saturday, Dec 26

AFROBEATS SATURDAYZ @ MASADA: Last Last 2026

Masada Nightclub

Dance at Chicago's top Afrobeats party. A vibrant night for music lovers and partygoers.

Sunday, Dec 27

DAVE SPECTER

Buddy Guy's Legends

Join Dave Specter for a night of live music at Buddy Guy's Legends. Ideal for jazz and blues enthusiasts.

Wednesday, Dec 30

TBA- Host The Jam

Buddy Guy's Legends

Join an exciting open mic night at Buddy Guy's Legends featuring acoustic performances and jamming. Perfect for music lovers.

Thursday, Dec 31

Jenny & Brad

Redhead Piano Bar

Celebrate New Year's Eve with Jenny & Brad at The Redhead Piano Bar. A memorable night filled with live music in Chicago.

Thursday, Dec 31

NYE CHAMPAGNE SHOWERS Afrobeats, Amapiano, Dancehall, Hiphop & RnB Classic

Masada Nightclub

Ring in the new year in style at Masada Nightclub with a night of Afrobeats, Amapiano, and more. A vibrant party for music lovers.

Thursday, Dec 31

New Year’s Eve: Sparkle Into The New Year | Trump Chicago | River North

Trump International Hotel & Tower® Chicago

Ring in the new year with skyline views and live entertainment at Trump Chicago. Ideal for those seeking a glamorous celebration.

Thursday, Dec 31

Sparkling Queen!: New Year’s Eve

Metro

Join the Sparkling Queen! New Year’s Eve event at Metro for a night of music and performances. Perfect for party-goers.