Where to Hear Jazz and Blues in Chicago

By Dave Lifton (@daveeatschicago)

As much as Chicago is associated with jazz thanks to Prohibition and the musical Chicago, there is no distinct sound that originated here. The first wave of jazz in Chicago was made by musicians who came to the Windy City from New Orleans in the early years of the Great Migration. This included Louis Armstrong, who lived in Chicago for most of the 1920s and cut his seminal early sides here. Rather, its jazz history is found in the list of musicians the city has produced, including Quincy Jones, Nat King Cole, Herbie Hancock, Benny Goodman, Coleman Hawkins, Gene Krupa, Ramsey Lewis, Jack DeJohnette, and Clifford Jordan.

The traditions created by those artists can be heard nightly in clubs throughout Chicago. The most famous is the Green Mill Cocktail Lounge in Uptown, which opened in 1915 and was a favorite hangout of Al Capone (arrive early to be seated in his booth). The acts lean towards older jazz; you’re unlikely to hear something that doesn’t swing. And it’s proudly old- school—cash only, no reservations, and no fancy cocktails. The cover charge is $10 Sunday – Thursday and $20 on the weekends.

Those wishing to remain downtown have a pair of options. Andy’s Jazz Club in River North has 75-minute sets from the main act starting at 6 and 8:15 PM nightly, and a set from another musician or jam session at 10:30 PM. Diners can choose from a selection of steaks, pastas and seafood, as well as a large dessert menu. Reservations are required.

Across Michigan Ave. in Streeterville is Winter’s Jazz Club, where most of the acts are vocalists performing standards or instrumental sets dedicated to the work of one or two jazz legends. There are two 75-minute sets on Wednesday – Sunday, and guests can stay for the second if there is space. Advance tickets are recommended and there is a $10 one-drink minimum purchase per person per set.

Inside Printers Row’s historic Dearborn Station, Jazz Showcase has seen dozens of legends take its stage since its 1947 opening, including Dizzy Gillespie, George Benson, Bill Evans, Art Blakey & the Jazz Messengers, and Count Basie. These days, the 170-seat club features top local talent nightly, with sets at 8 and 10 PM, and a Sunday afternoon performance at 4 PM that’s free for kids 12 and under.

Despite its name, Le Piano in Rogers Park isn’t a piano bar. It specializes in cabaret, Latin jazz, and organ trios. The calendar is curated by owner Chad Willetts, who can also be found playing percussion on Fridays and Saturdays. While listening to the music, enjoy classic cocktails and a full dinner menu.

Most of Chicago’s jazz clubs focus on traditional or modern, but Roscoe Village’s Constellation is where experimental and avant garde sounds thrive. The club has a nonprofit arm that allows artists the opportunity to follow their vision without having to compromise to suit commercial tastes.

If Chicago never created its own subgenre of jazz, it most definitely has a distinct style of blues. In order to be heard above the din at raucous South Side clubs and the Maxwell Street Market, local blues musicians in the 1940s went electric. The harmonica became raw and distorted when played through microphones and the rhythms hit harder and were more precise because they were inspired by the factories the musicians were working in during the day.

Records by such luminaries as Muddy Waters, Howlin’ Wolf, Koko Taylor, and Little Walter made their way to England, where they influenced dozens of rock bands. The Rolling Stones even named themselves after Muddy Waters’ song. Their success in America led millions of teenagers to discover the source material, and helped sustain and grow the blues into the present day.

Guitarist Buddy Guy was a little younger than the bluesmen he played with, and is the one who is still alive as of April 2025. In 1989, he opened Buddy Guy’s Legends in the South Loop, and it remains a pilgrimage for blues lovers. On Wednesday – Sunday, the music starts with a free acoustic performance from 5:30 – 8 PM, and that’s followed by a ticketed show at 9 PM. Wednesday night’s entertainment includes a jam of local musicians. Diners can enjoy a Cajun/Creole menu that also includes burgers, chicken sandwiches and salads.

In Lincoln Park, Kingston Mines has been the home of Chicago blues since 1968. It has two stages, with bands alternating throughout the night, and a liquor license that keeps the music going until 4 AM on Friday and Saturday. Doc’s Kitchen offers a Southern-focused menu that is open late. Tickets can be purchased online or at the door.

The neon sign above River North’s Blue Chicago evokes the heyday of Chicago blues. For a cover charge of $15 on Wednesday, Thursday, and Sunday (one-drink minimum), and $20 on Friday and Saturday (two-drink), guests can see local stars like Chicago Blues Hall of Famers Sheryl Youngblood and Mike Wheeler.

There’s no sign outside Rosa’s Lounge in Logan Square, however, just a mural of a guitarist. Founded in 1984 by Tony Mangiullo, who was befriended by Chicago harmonica legend Junior Wells in Italy, Rosa’s has long been considered the heart of the local blues scene. Every year, a stage at the Chicago Blues Festival in Millennium Park is devoted to the musicians who play there.

The author’s favorite Chicago jazz song is Louis Armstrong’s “West End Blues,” and his favorite Chicago blues track is Howlin’ Wolf’s “Smokestack Lightnin’.” He wrote this while listening to probably the greatest Chicago blues album, Magic Sam’s “West Side Soul.”

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