Since the early twentieth century, Chicago has been a hotbed for music, from its own hybrids of jazz and the blues to Lollapalooza-style rock ’n’ roll. Today, you can still see vivid examples of how this city has helped make music history. Take Chicago-style blues—made famous by artists such as Muddy Waters and Howlin’ Wolf—and which came about thanks in part to the “Great Migration” of African-American workers from southern states. Likewise, Chicago jazz—and greats such as Jelly Roll Moton and Louis Armstrong—came from talented artists who migrated to Chicago and introduced uptempo New Orleans-style jazz to Chicago’s South Side From these genres have sprouted Windy City takes on gospel, soul, house and a lot of rock ’n’ roll—including American legends such as Wilco. Music is still a huge part of Chicago culture. Jazz? Blues? Classical? Contemporary? The only challenge you face is narrowing your options—but here is where you can see the city’s musical past, present and future up close.
The Green Mill
It's a hike. But, Green Mill's status as one of the oldest jazz clubs in the country (it opened in 1907)— including well-documented visits from Charlie Chaplin and Gloria Swanson—make this trek to Al Capone’s former speakeasy in Uptown more like a pilgrimage. Locals revel in the wrinkle-in-time ambiance as much as the standout jazz.
Tucked into the shadows of stately Gold Coast brownstones, thing tiny-yet-tony piano bar is filled with kitschty-cool zebra memorabilia. Opened the day Prohibition ended—December 5, 1933—the quirky watering hole’s offerings of hardcore martinis and lively piano players, banging out jazz, blues and , make it perfect for a nightcap.
Andy’s Jazz Club
For more than 40 years, this upscale River North spot has been quenching Chicagoans’ thirst for jazz. And, they do so more than once a day. Its famous “jazz at five” features local acts at 5 pm with a return set at 9:30. It’s perfect for the enthusiast with an early bedtime. Reservations required.
The mantra at this Chicago institution is indicative of the club’s riotous energy: “hear the blues, drink booze and talk loud.” Founded in 1968, this Lincoln Park “Blues Emporium” is the city’s oldset and largest blues venue. Musical legends such as B.B. King—as well as plenty of locals—perform on its two stages, seven nights a week, until 4 a.m.
Housed in a turn-of-the-century Schlitz Brewery tap house, this small Lakeview venue offers a mixed bag of bands seven nights a week. Featuring anything from honky tonk, indie rock, pop, funk and even mariachi, this laidback spot is a music lover’s paradise. Bonus: The free acoustic brunch on Sundays, featuring local talent.