The best songs about Chicago.
This multi-genre list of songs just screams Chicago.
Unapologetic, melting-pot, broad-shouldered, gritty, cold: Chicago’s common descriptors fall short in capturing its peculiar vibe, so I turn to Chicago’s music to answer the call. Chicago has lifted the voices of some truly legendary artists who have been essential to the formation of many of the sounds we love: blues, jazz, hip hop, house, and indie rock to name a few. Many of these groundbreaking artists turn back to the city that formed them, whether consciously or not, and express their love for it through music stylings. These songs are not necessarily odes to Chicago—I don’t think Chicago is well-disposed to odes—but sights and sounds, memories, feelings that make the Windy City stand still for a moment in our minds. This collection of songs would make an unlistenable playlist, but that is only fitting for this one-of-a-kind city. Here is a list of ten songs that, to me, scream ‘Chicago.’
Alliotta Haynes Jeremiah, “Lake Shore Drive”
Chicago has range, too much range for one song. But this song, which only tries to describe a single road, captures it entirely. If you didn’t know, Lake Shore Drive is the highway next to Lake Michigan that runs North/South across the entirety of Chicago. With its stunning skyline views and lake breeze, it is an urban highway like no other. The songs' arpeggiating chords are thrilling, and grow more and more complex after each verse, reminiscent of the swelling feeling of approaching downtown Chicago on Lake Shore Drive. Funnily enough, the road shares an acronym with a common hallucinogen, which the song may partially be about.
Kanye West, “Homecoming”
This is the song I played while landing in Chicago for the first time, and since then, “Homecoming” has been a go-to Chicago song for me. Chris Martin’s smooth vocals, Kanye’s earnest storytelling, and a piano riff that doesn’t get old combine to create a sound that is as vigorous and broad-shouldered. Chicago references are littered across Kanye’s discography (“two words, Chi-town, Southside, worldwide/Cuz I rep that til I f*ckin’ die” from “Two Words,” for example). But there’s nothing like arriving back in your hometown, and in this song, Kanye seems pretty happy to be back.
Chicago, “Saturday in the Park”
Firstly, note that the band is called “Chicago.” If you haven’t heard of them, they're one of Chicago’s greatest and most enduring contributions to pop music—and this is their best song. This song was apparently inspired by some film of Central Park that Robert Lamm discovered, but don’t read too much into that, it’s about Chicago. They re-released it last year on their EP Summer in Chicago, and that’s good enough for me. The intro is irresistible: it sounds as if Lamm is just having fun banging around on the piano, until Chicago’s ensemble is delicately introduced. A Saturday in a Chicago park on the fourth of July sounds like a good time to me.
Sufjan Stevens, “Chicago”
I cannot quite place why, but something about the bells at the beginning of this song are quintessentially Chicago. “Chicago” is the fitting centerpiece of Sufjan Stevens’ brilliant album Illinois. The Chicago-born artist is known for his delicate, subtle sound, but this song quickly crescendos to an anthemic dynamic after the soaring melody of the strings begins. The song’s lyrics take on loss and finding new beginnings, and Chicago is mixed up in all of it.
Frank Sinatra, “Chicago”
This is a true ode to Chicago, like only Frank Sinatra can do. Though “Theme from New York” might be more grand and flashy, Sinatra clearly attaches more sentimental value to Chicago, his hometown. It sounds a bit like a show tune, is bluesy, and, for a variety of reasons, sounds like a Chicago of the past. Still, Sinatra's distinctive talent for using unremarkable words to capture vivid feelings—such as "I saw a man who danced with his wife/In Chicago, Chicago, my hometown"—is what makes this song so charming.
Saba, “An Interlude Called “Circus””
I only wish this song were longer, similar to Chicago-rapper Saba’s opinion of the year 2012. Those were the days before fame and success, when he just spent his time “chilling on the West Side.” This song is delicate, forceful, nostalgic and energetic all at once. The portrayal of Saba’s Chicago upbringing is almost blissful, but is tempered by his dangerous surroundings: “this Chicago, when we leave we say ‘Be safe’ here.” It is an outburst of joyful reminiscence that is one of Saba’s best.
Djo, “End of Beginning”
Djo’s enveloping sound and heartfelt hook, “And when I’m back in Chicago, I feel it” is reason enough for this song to make the list. “End of Beginning” is pure nostalgia from an artist who went to college in Chicago and then made it big. The dreamy synth pop is introspective and speaks to how a city can define a piece of oneself, because one can “take the man out of the city, not the city out the man.” Too true.
Chance the Rapper, “65th and Ingleside”
The list would not be complete without Chance the Rapper. He is maybe the central figure of Chicago progressive hip hop in the 2010s, and it could be argued that an address has never put anyone in their feels more than Chance in this melancholy single. The song is not about Chicago per se, but as he reminisces about his early relationship with his now-wife and their escapades through his hometown, he gives us a tour of his Chicago, from ‘Dro City’ to downtown to Evanston. This song is criminally underrated: I would go so far as to say he hasn’t topped it since its 2018 release.
Common, “Chi-City”
The artist fka Common Sense (“from the city of wind”) is a hugely influential figure in the development of conscious rap and a Chicago legend. “Chi-City” sees him operate at his best, with a funky, catchy beat that is hard to top. Not only is Common a Chicago icon, but this album, Be, is particularly about Chicago and littered with references to it: “the chosen one from the land of the frozen sun” from the record’s intro is a favorite of mine. (By the way, ‘Chi-city’ is the best nickname for Chicago.)
Moby, “South Side”
This song is a standout on Moby’s hugely influential Play, an album that would redefine electronic music, and does not sound nearly fifteen years old. Inspired by Moby’s trip to Chicago, the song is an abstract journey through the city, as Moby rides through the four “sides” of Chicago. The strident tone of the verses create a sense of urgency, which gives way to a harmonious chorus that is revitalizing. Both the tone and lyrical content of the song present a picture of a nuanced Chicago “where there’s light and darkness.” Though the song is hardly a glorification of Chicago, it speaks to the city’s role as a source of inspiration. And with Chicago being the birthplace of house music, I had to include something a little electronic.
I’ll close with some honorable mentions:
King Von, “Took Her To the O”
King Von was briefly the face of Chicago gangsta rap before his tragic death, and this gritty, hard-hitting song about a notorious Chicago street is easily his best.
The Rolling Stones, “2120 South Michigan Ave”
The address of a historic blues and rock ‘n roll studio in Lincoln Park, the Stones go for blues on this song dedicated to Chicago’s music history.
Robert Johnson, “Sweet Home Chicago”
One of the most important figures in blues history, this Chicagoan wasn’t too busy changing the game to show Chicago some love.
John Summit, “In Chicago”
“I’m drunk and I’m high and I’m in Chicago” are a few lyrics to this catchy dance hit where Chicagoan John Summit illustrates his sense of Chicago’s club scene.
flipturn, “Chicago”
This song is about an outsider’s dreamy vision of Chicago rather than the Windy City itself. Either way, the chorus is powerful and I dig the way he sings “Chicago.”
edited by Vikram Mahendru.
artwork by Peter Cross.
album artwork believed to belong to either the publisher of the work or the artist.