Perhaps more so than most other major metropolises, Chicago is a city that needs to be experienced with your ears. The roar of the crowds at Wrigley, the squeal of the “L” train passing overhead, the sizzle of street food at the Maxwell Street Market — so many sounds evoke the true essence of the Windy City. And the city’s characteristic cacophony is only supported by the melodies of its music scene. From the post-Great Migration emergence of Chicago Blues and jazz to the rock and house scenes of the ’70s and ’80s to the more-recent explosion of hip-hop and independent rap, Chicago has been at the forefront of the music world for the better part of the last century. Want to feel like you’re walking the streets of the Loop, even from the comfort of your own home? Queue up our Chicago playlist. 

With that in mind, here’s a carefully curated playlist of Chicago tunes to cue up the next time you’re walking through Chi-Town.

“Angels (feat. Saba)” by Chance the Rapper

It’s difficult to overstate Chance the Rapper’s influence, not just on his home city of Chicago but on the music industry as a whole. He first introduced his unique style — an eclectic mix of colorful funk, uplifting gospel, and soothing psychedelia — with 2012’s “10 Day,” a mixtape he recorded during a 10-day high-school suspension, but he launched himself into the national discussion with the following year’s trippy “Acid Rap.” In the years since, with the release of his Grammy-winning “Coloring Book” and countless collaborations with other popular artists, he’s become practically the biggest name in music, unmatched in his endless commitment to creativity.

With the spotlight constantly trained on him, Chance has refused to bask in it, choosing instead to train it back on his home city. Over the past few years, he’s hosted dozens of open-mic nights across Chicago, encouraging the city’s high-schoolers to take to the stage and perform rap, poetry, and other original compositions. Additionally, following an unsatisfactory 2017 meeting with governor Bruce Rauner, Chance donated $1 million to Chicago Public Schools. While much of his music reflects his love for the city, “Angels” stands as a testament to the relationship he shares with it, showcasing not only the love he has for Chicago, but the love that city has returned to him as well.

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Mustang Sally” by Buddy Guy

Chicago Blues, which developed as a result of the Great Migration in the first half of the 20th century, is notable for its jazzy feel and instrumental variety. One hallmark of the genre was its introduction of electric guitar, an instrument mastered by Chicago Blues legend Buddy Guy. Guy was named the 30th greatest guitarist of all time by Rolling Stone, and his influence can be felt in the music of other blues and rock gods such as Eric Clapton and Jimi Hendrix.

While “Mustang Sally” wasn’t his song originally (that honor goes to Mack Rice, though you’re probably more familiar with the Wilson Pickett cover), Guy’s version remains an undeniable jam that showcases his unique and unpredictable rhythm. Whether you’re riding a Mustang through the city’s streets or just walking around, “Mustang Sally” is sure to provide a great beat to your Chicago exploration.

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Chicago” by Sufjan Stevens

More of a quintessential road-trip ballad than a Windy City anthem, Sufjan Stevens’ “Chicago” might be a good selection for the opening to your playlist, a tune to press play on as you head east on I-80 and the unmistakable Chicago skyline becomes visible across Lake Michigan. With a relentlessly uplifting beat and a passionate turn from the trumpet, the song has become a favorite among fans of the indie-folk idol, and it’s often the tune he chooses to close out his concerts. If you do listen to it, however, be sure to cue up something else catchy afterward — otherwise you’ll find yourself humming the melody throughout your entire trip. Don’t say we didn’t warn you.

Go Cubs Go!” by Steve Goodman

Anyone who’s ever lived with a Cubs fan knows this song — and they most likely hate it. The cheesy tune is played throughout Wrigleyville and the living rooms of fans around the world whenever the Cubbies win a game (which, until recently, didn’t happen that often). It’s a bouncy melody that features folk singer Steve Goodman crooning about the fact that “this is the year” and that “they got the power; they got the speed,” a lacking argument that soon gives way to endless iterations of the song’s gnawing chorus: “Go Cubs Go! / Hey Chicago, what do you say? / The Cubs are gonna win today.” While it’s a somewhat awkward and childish hometown favorite, the song feels undeniably fitting for the fans of the Lovable Losers, and you can’t help but respect them for the shameless way they belt it out after their infrequent victories, often double-fisting cans of Old Style as they sing along.

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Saturday in the Park” by Chicago

I was surprised and slightly dismayed to learn that despite the appropriate name of the band that sings it, “Saturday in the Park” takes place nowhere near Chi-Town — in fact, the park in question lies about 700 miles to the east. The band’s keyboardist, Robert Lamm, was inspired to write the song after walking through Central Park in New York City on July 4 of 1971 (which, equally disappointingly, was actually a Sunday…). Geographical dissonance aside, the song remains a great, relaxing tune to pop on during a stroll around one of Chicago’s beautiful green spaces.

Homecoming” by Kanye West

His recent political stunts — and many of his prior ego-driven antics — might make you wary of turning to Kanye for your next playlist addition. But, if you focus solely on his music, it’s difficult to deny how truly gifted this artist is. Part-rapper, part-producer, part-fashion designer, part-entrepreneur, Kanye is one of the most acclaimed musicians to come out of Chicago in the past few decades — or, really, of all time. He’s won 21 Grammy awards, he’s earned three spots on Rolling Stone’s “500 Greatest Albums of All Time,” and he collaborates regularly with other major artists such as Jay-Z, Rihanna, Kid Cudi, and Frank Ocean. Any discussion of Chicago hip-hop is incomplete without mentioning Kanye West.

In “Homecoming,” Kanye compares the city to a past girlfriend, asking: “Do you think about me now and then? / ’Cause I’m comin’ home again.” Like many of his songs, the lyrics are layered eloquently, but here, it’s the beat that gives the tune its character — a heavy piano-riff bass line that will have you bopping down Michigan Avenue.

Your Love” by Frankie Knuckles

One of the more unique musical movements to originate in Chicago, house music developed in the city’s underground dance club scene in the early 80s. The genre is characterized by repetitive rhythms and beats, as well as synthesized bass lines, and it was originally concocted when club DJs started applying heavier beats to pop disco tunes. Pioneering the movement was Frankie Knuckles, a DJ who eventually became known as “the godfather of house music.” Though it started as an underground trend, house music eventually grew to become popular all around the world, and today, it’s evolved to include a variety of acts including Daft Punk, Avicii, and Skrillex. Knuckles’ club hit “Your Love” is considered a classic of the genre.

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Mannish Boy” by Muddy Waters

A necessary addition to any discussion of the city’s music, Muddy Waters is often considered the “father of the Chicago Blues movement.” And even if you don’t think of yourself as a blues aficionado, you’re most likely familiar with this tune. Its central call-and-response guitar riff is unmistakable and has been used in countless movies and shows (notably, in “Goodfellas”), as well as the George Thorogood song “Bad to the Bone.” If you’re walking through the city and want something deep and gritty to put a little pep in your step, this is the song to select.

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Chelsea Dagger” by The Fratellis

As an avid Boston Bruins fan, I’ll be the first to point out that “Chelsea Dagger,” the unofficial anthem of the Chicago Blackhawks, makes no mention of the Windy City throughout its three-and-a-half minutes of non-stop rock-and-roll. But, nevertheless, the insufferable Blackhawks fans have monopolized it, playing it after every Chicago goal (which, I concede, unlike Cubs wins, come fairly often) to the point that it’s become synonymous with the city’s immense hometown pride. If you can put all that aside, you’re in for a rollercoaster ride of a rock song.

Cubs in Five” by The Mountain Goats

If you’ve never heard of the Mountain Goats, the indie-folk group fronted by writer John Darnielle, the good news is that you’ve got plenty to catch up on. Highly prolific, the band has released 16 studio albums and 23 EPs for a total of over 500 songs, and each one is exquisitely poetic, overlaying beautifully inspiring melodies with poignant, often heartwrenching lyrics.

“Cubs in Five” is one of their best and, also, one of their most uplifting. Declaring confidently that the Cubs will win the World Series and the Tampa Bay Buccaneers will win the Superbowl, it sounds off as an unapologetic anthem of the underdog. As the song progresses, Darnielle makes more and more hopeful — yet unlikely — predictions: intelligent life will be discovered in outer space, “the Canterbury Tales” will skyrocket to the top of the bestseller list, and Philip Morris International (the multinational tobacco company) will “admit that they made an awful mistake.” It starts to become clear that none of this is likely going to happen, but that doesn’t mean there’s any reason to stop having faith that it could. And as a city that’s played the part of the underdog many a time, Chicago understands this more than any other.

Wonderful Everyday” by The Social Experiment

This jam from the Social Experiment — Chance the Rapper’s band with frequent collaborators Nico Segal, Peter Cottontale, Greg Landfair Jr., and Nate Fox — is the sort of relentless song you can play 20 times in a row and never grow tired of. Sampling and remixing the theme song to the children’s cartoon “Arthur,” the track opens with dreamy piano riffs and varied incantations of the phrase “it could be wonderful every day” before interjecting the original lyrics of the theme (“Every day when you’re walking down the street / Everybody that you meet / Has an original point of view”) and eventually transitioning to the funky final verse, an upbeat repetition of the following:

“I’m gonna get by when the going get rough / I’m gonna love life ‘’til I’m done growing up / And when I go down / Imma go down swinging / My eyes still smiling / And my heart still singing.”

Though he doesn’t shy away from heavy subjects when he needs to, Chance is, more often than not, a refreshingly optimistic artist, and that joy is on full display here. So, the next time you find yourself walking down the streets of Chicago, throw this one on, let your worries go, and enjoy the day.

Cover photo by Elliot Image

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Devon Shuman
Devon Shuman is a creator, a storyteller, and a traveler from Boston, Massachusetts. He caught the travel bug at a young age when his family would take camping trips in southern Maine and New York’s Adirondack region. Since then, his adventures have taken him all across the globe. His favorite journeys include island hopping in the Galápagos, thru-hiking Vermont’s Long Trail, and summiting Mount Kilimanjaro. He currently works as an editorial consultant for Passion Passport, helping explorers from around the world tell their stories.