There isn’t a better time capsule of Chicago’s Jazz Age than this Uptown lounge, which opened over a century ago—first as an after-work haunt of Charlie Chaplin, then as a Prohibition-era gangster hangout. (Al Capone’s favorite velvet booth sits close to one of the room’s secret escape hatches.) Today it’s the oldest continuously running jazz club in the country, where Art Deco fixtures, mood lighting, white tablecloths, and strong martinis are all part of the immersive experience.

It might be served up Chicago-style or from the Delta, but at Kingston Mines you’re going to hear the blues 365 days a year and late into the night. The oldest continuously operating blues club in the city, the orange Halsted Street spot has been a favorite among cult-status musicians who have swarmed to its two stages since 1968; Bob Dylan and Mick Jagger like to stop by when they’re in town. The digs are decorated like an old-school juke joint, and decent soul food is served.

The third-oldest liquor license in the city belongs to this tiny Gold Coast hideaway, a lively piano bar nestled on the first floor of the stately Canterbury Court apartment building since 1929. Seven nights a week, the dimly lit lounge’s rotating roster of in-house pianists bangs out a mix of old standards and random requests, from Billy Joel to Snoop Dogg. Expect the snug space to be standing room only—and to sing along.

Tucked away on a cobblestone side street, the relatively new Le Piano brings French salon vibes to the North Side neighborhood of Rogers Park. Lit by candles and filled with antiques, the cozy space hosts blues, cabaret, and Latin jazz showcases, punctuated by the rumble of passing Red Line trains. But the pièce de résistance is the grand piano, underneath which patrons are occasionally invited to lie down and let the keys reverberate over them.

True blues heads can bypass the tourist crowd entirely at this off-the-beaten-path Logan Square lounge, opened in 1984 by mother-and-son Italian immigrants and inspired by the smoky South Side clubs that once established Chicago as the world’s blues capital. Legends like Junior Wells, Pinetop Perkins, and Homesick James have graced its colorful stage; these days, Mama Rosa’s residents include local blues heroes like Jimmy Burns and Lil Ed Williams.

The iconic bluesman opened his South Loop club in 1989 as part of his promise to Muddy Waters to keep the genre alive on the South Side. Decorated with checkerboard floors and overflowing with memorabilia (plus a hand-painted mural of Chicago blues’ Mount Rushmore), the brick building has hosted performers mythic enough to suit the name: Koko Taylor, B.B. King, Stevie Ray Vaughan—not to mention the place’s namesake, whose month-long residency sells out every January.

Though Andy’s began in the ’50s as a grungy post-work hangout for newspaper pressmen, it emerged in the ’70s as one of the city’s trustiest spots for traditional jazz and lunch or dinner. Its Jazz at Five and Jazz at Nine traditions are still alive today, spotlighting international and local acts beneath charmingly retro neon and a dusty Wall of Fame. Grab a Schlitz and get comfortable.

For those seeking jazz in the heart of Downtown, this relative newcomer (it opened in 2016) is blocks from Navy Pier and tucked into the Chicago Riverwalk. It’s all about the intimacy at Winter’s, an elegant 100-seat room with excellent acoustics for its two nightly sets of straight-ahead jazz ensembles. It’s more of a listening environment than a social club, which is to say less chitchat, more jazz.

Since opening in 1947, the South Loop club—now located in a historic 19th-century train station after many location changes—has been a temple to jazz in all forms. Its late founder, Chicago jazz godfather Joe Segal, once forbade smoking and talking in order to focus on the music, from pioneers (Charles Mingus) to experimentalists (Sun Ra), with a soft spot for the bebop style of Charlie Parker. Today the art-filled 170-seat space is operated by Segal’s son Wayne, keeping the tradition alive.

The most cutting-edge jazz in the city right now can be found in a factory-like brick building (the former Viaduct Theater) along the North Branch of the Chicago River. Since Constellation’s opening in 2013, the emphasis has been on all things experimental: free jazz, improvisational music, contemporary classical, and other mind-expanding sounds, including several performances from the Sun Ra Arkestra.