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CHICAGO MUSICAL
TOUR

BY JEN ROSE SMITH

Discover The Windy City’s Musical Heritage — from Ragtime to Hip Hop

“Chicago, Chicago, I will show you around — I love it,” sang Frank Sinatra. “Betcha bottom dollar you’ll lose the blues in Chicago, Chicago.”

 

Sinatra crooned it, Kanye rhymed it, and Louis Armstrong blew it ― Chicago is a music town. “You can trace almost every form of music back here,” says writer, illustrator, and musician Steven Krakow, who chronicles the city’s musical legacy in The Secret History of Chicago Music, a long-running comic in The Chicago Reader. “Jazz started here in the dawn of Chicago,” Krakow explains. “People come from all over the world to hear blues and see the historic places here.”

 

When African Americans arrived from southern states in the Great Migration at the start of the 20th century, they brought fresh sounds and talent that captivated the city. “All of a sudden there’s Delta Blues music here,” notes Krakow, “that sort of turned into electrified Chicago blues.” Chicago transplants like Jelly Roll Morton and King Oliver pushed the boundaries of American music of the time, crafting sounds that still echo through a grab bag of genres today.

Cue the perfect playlist for exploring Chicago’s musical landmarks, and you’ll get a genre-spanning crash course in midwestern melodies, from traditional folk to punk rock to rap. What you find might surprise you, says Krakow: “It could take you anywhere.” 

 

It’s also a legacy written in the neon lights and scuffed dance floors across Chicago, where ground-breaking studios, clubs, and stages continue to invite musical exploration. Dance through Chicago’s musical history on this toe-tapping tour of storied lounges, legendary eateries, and record shops ― starting with these favorites ― and discover the city’s rhythm and flow for yourself.

Green Mill Cocktail Lounge

A twinkling constellation of neon welcomes revelers to this roadhouse-turned-club on the corner of Broadway and Lawrence that reeled through the Jazz Age with highball in hand. You can still slide into the booth where Al Capone liked to drink; beneath your feet will be a series of tunnels that have served as an escape hatch for fleeing mobsters. But it’s the Green Mill’s jazz chops that make this a harmonious highlight, since the crowd’s been enchanted over the decades by everyone from Billie Holiday to Tommy Dorsey, Bix Beiderbecke, and Benny Goodman.

4802 North Broadway, greenmilljazz.com 

Willie Dixon’s Blues Heaven Foundation

Chuck Berry, Aretha Franklin, and Howlin’ Wolf all laid down tracks in Chess Records’ South Michigan Avenue studio, a musical Mecca that’s now home to Willie Dixon’s Blues Heaven Foundation. Dixon, a blues musician and producer, helped steer the Chess Records sound, and his family has filled the former studio with a trove of instruments, musical memorabilia, and rare records. If you can’t recall the address, just cue up the Rolling Stones: The band recorded the instrumental “2120 South Michigan Avenue” here, along with the rest of their bluesy EP Five by Five.
2120 South Michigan Avenue, bluesheaven.com 

Reckless Records

Vinyl hounds make a beeline for this storied record shop, where bins of new and used albums invite afternoons of browsing Chicago greats. Visit the wall of staff picks for a deep, genre-hopping dive into musical arcana, or flip through the shelves on a tuneful search for hidden treasure. The real-life Reckless Records shares a neighborhood with the fictional record shop Championship Vinyl from the 2000 movie High Fidelity, starring Chicagoan John Cusack.
1379 North Milwaukee Avenue, reckless.com 

Buddy Guy’s Legends

Blues takes center stage every night here, at a club that welcomed superstars like Stevie Ray Vaughn and Junior Wells, as well as where up-and-comers take a shot at the national stage. You might even spot Buddy Guy himself, as the Rock and Roll Hall of Famer stakes out a spot at the bar when he’s in his adopted hometown. He also plays to sold-out crowds there during an annual residency each January, fulfilling his promise to blues legend Muddy Waters, who, on his death bed, asked Guy to swear he would keep the blues alive.
700 South Wabash Avenue, buddyguy.com 

Harold’s Chicken Shack 

“Give me a six pack and a half of Harold’s chicken,” raps Common in the song “Chapter 13 (Rich Man vs. Poor Man).” This Chicago institution serves perfectly fried birds over fries and white bread, and while the chicken alone is worth the trip, the chain’s also earned shout outs from Kanye West and Lupe Fiasco. To find out if you agree, head to one of the many chicken shacks located across the city. While every Chicagoan has a favorite, Chicago magazine handed top honors to Harold’s Chicken Shack No. 88 in Bronzeville, home to a who’s-who of Chicago musical greats including Herbie Hancock and Sam Cooke.
124 East 35th Street

Old Town School of Folk Music

Check the amplifier at the door; the musicians here are keeping folk traditions alive. Pete Seeger, John Prine, and Mahalia Jackson all played here as the music school strummed its way through the 1960s and early 1970s. Today, concerts range from old timey tunes to the wide-ranging sounds of the Global Dance Party, with upcoming dates featuring Arlo Guthrie and Loudon Wainwright III. Music shops at the two locations stock ukuleles, banjos, and guitars of every shape and size. 4544 North Lincoln Avenue & 909 West Armitage Avenue, oldtownschool.org

Fireside Bowl 

Aim for the pins at this neighborhood bowling alley, and you’ll be rolling where punk greats once thrashed and screamed. From 1994 to 2004, Fireside Bowl earned a hard-charging rep as one of America’s best punk rock venues. Five dollars got you on the dance floor for shows by the likes of Sleater-Kinney, Tortoise, and the Chicago-based Alkaline Trio. Pay your respects by bowling a set over cheap pitchers of beer. 
2646 West Fullerton Avenue, firesidebowl.com 

Sam Cooke Way

Remember the late, great “King of Soul,” Sam Cooke, with a stroll along a segment of 36th Street in the historic Bronzeville neighborhood. A sign honoring the crooner has pride of place at the corner of East 36th Place and South Ellis Avenue, close to Cooke’s onetime family home. It’s also just a few miles from the funeral home where Cooke was honored by some 200,000 fans after he was shot to death at age 33.
3601 South Ellis Avenue

Jazz Showcase

Chicago’s oldest jazz club has hosted an honor roll of musical greats, from Bill Evans to the avant-garde Art Ensemble of Chicago. Dizzy Gillespie used to celebrate his birthday here by blowing through annual shows, while owner Joe Segal helped found the Jazz Institute of Chicago. Now the long-running club keeps the calendar packed with jazz musicians from across the globe. Don’t forget to snap a selfie with the street sign; South Plymouth Court officially turns into Joe Segal Way right in front of the club.  806 South Plymouth Court, jazzshowcase.com 

Marina City Towers

When the band Wilco chose an artsy shot of the Marina City towers for the cover of their album Yankee Hotel Foxtrot, the band transformed a Chicago landmark into a must-see destination for fans of indie rock. That wasn’t the towers’ first star turn. They also appeared on Sly and the Family Stone’s album There’s a Riot Goin’ On and were part of Mercury Records’ former logo. The buildings’ residents also brought some serious musical chops: John Denver enjoyed a perch on the 47th floor. Check out the towers on your way to a lively Gospel Brunch at the next-door House of Blues Chicago on Sunday mornings. 300 North State Street & 329 North Dearborn Street, houseofblues.com/chicago

Johnny Twist Blues Museum

Take a slow dive into Chi-town’s blues legacy at this tiny, quixotic museum, which welcomes visitors with a hand-painted sign proclaiming “Hey hey blues are cool.” Inside is a deeply personal collection of memorabilia and music gathered by blues guitarist Johnny Twist, who has appeared with legends like Howlin’ Wolf and Buddy Guy. Music collectors can find gems worth dusting off the cassette tape player for here. 
6455 South Cottage Grove Avenue