Free Jazz Shows in Chicago

Join us every Monday for our weekly jam session at Le Piano! We welcome musicians, vocalists, and artists of all kinds to step up, share their talent, and celebrate the joy of live music. $10 Cover

Back to All Events Relax Attack Jazz Series: Clif Wallace (DJ set) - June 2026 Edition Wednesday, June 24, 2026 9:00 PM 10:00 PM Google Calendar ICS This week, we’re flipping the script. Instead of a live band, the Relax Attack Jazz Series welcomes drummer, producer, and all-around vibe architect Clif Wallace behind the decks for an all-vinyl DJ set. A true multi-hyphenate — drummer, DJ, radio host (WDCB 90.9FM), composer, bandleader, and tastemaker — Clif brings his boundless love of music to every record he spins. His selections move through jazz and beyond, tracing grooves, moods, and rhythms that keep the night alive. Come ready to listen, sip, and move. This one’s all about deep cuts, warm sound, and good company. @cwjams Every Tuesday and Wednesday at the Relax Attack Jazz Series , we present Chicago’s top jazz artists in a lively atmosphere, full of cocktail-shaking and spirited conversation. 6pm doors / 9pm show / 2 sets / no cover Tagged: Wednesday Previous Previous June 23 Tromblau & ALL THE FRIENDS: Birthday Celebration Next Next June 25 Prosperity Room (June 2026 Edition)

Thu, Jun 25, 5:00 PM

ANDY BROWN

Green Mill / Uptown / Map

(5pm – 7:15pm) ANDY BROWN Thursday June 25 5:00pm - 7:30pm Andy Brown No cover charge

(3pm – 5pm) PAPER MACHETE Saturday June 27 3:00pm - 5:00pm FREE Doors open at 1pm

Join us every Monday for our weekly jam session at Le Piano! We welcome musicians, vocalists, and artists of all kinds to step up, share their talent, and celebrate the joy of live music. $10 Cover

Back to All Events Relax Attack Jazz Series: Jimmy Bennington Colour and Sound Tuesday, June 30, 2026 9:00 PM 10:00 PM Google Calendar ICS “Once mentored by Elvin Jones, Chicago-based drummer Jimmy Bennington celebrates over 35 years in the music field... Bennington's unique sound and loose drumming, which doesn't follow traditional rhythmic patterns... and leaves quite a bit of room to freedom." DownBeat Magazine Every Tuesday and Wednesday, we present Chicago’s top jazz artists in a lively atmosphere, full of cocktail-shaking and spirited conversation. 6pm doors / 9pm jazz / 2 sets / no cover Tagged: Wednesday Previous Previous June 30 I've Created A Thing That Will Never Bring Me Pleasure ( A Poetry Reading)

Thu, Jul 2, 5:00 PM

ANDY BROWN

Green Mill / Uptown / Map

(5pm – 7:15pm) ANDY BROWN Thursday July 2 5:00pm - 7:30pm Andy Brown No cover charge

(3pm – 5pm) PAPER MACHETE Saturday July 4 3:00pm - 5:00pm FREE Doors open at 1pm