10 Of The Best Songs About Illinois: Prairie State Playlist

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Written by Laura Macmillan
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When you think about the places in the United States that have inspired the most musical representations, your mind might jump to California, New York, or Texas, but the truth is that every state has been home to musical geniuses. Any place can inspire beautiful songs, and few places have better songs than the great state of Illinois.

Sitting at the crossroads of the United States, Illinois is the anchor of the Midwest, representing the place where just about everything, from trade and art to culture and music, intersects. The state has a connection to both coasts and the rest of the Midwest, and it has nourished a variety of musical styles, from Chicago blues to hip-hop. 

In this post, we’re going to take a look at ten of the best songs about Illinois, the Prairie State. Let’s get started.

Related: Check out our list of songs about Chicago.

1. “Chicago” By Sufjan Stevens

Topping our list of the best Illinois songs is Sufjan Stevens’s “Chicago.” It’s hard to elevate one song as the best on Stevens’ sensational album Illinois, which takes a panoramic view of the state and its people. But “Chicago” is our pick for the best. 

In contrast to the lowkey style of most of our singer’s songs, “Chicago” features a symphonic wall of sound narrating a young man’s journeys through the Illinois area as he comes of age.

Stevens’ dulcet tones and poetic lyrics paint a picture that elevates Illinois into the world of mystical experience.

2. “Chicago (That Toddlin’ Town)” by Frank Sinatra

One of two Sinatra odes to the Illinois metropolis (the other being the Academy Award-winning tune “My Kind of Town,” which we’ll also get into later), “Chicago, That Toddlin’ Town” might have a silly name, but it does represent a classy and classic ode to Chicago, Illinois, and its history.

Throughout the crooning song, Sinatra traverses time and space in Chicago history, tying them together in praise of the city.

He makes special note of the joie de vivre that seems endemic to Chicago: he reports that “you won’t lose the blues if you go to Chicago” and that even prohibition couldn’t shut the city down.

And, well, who are we to argue with Sinatra?

3. “65th And Ingleside” By Chance The Rapper

Along with Lupe Fiasco (who will appear later in this list), Chance the Rapper is one of the most famous hip-hop artists to come out of Illinois.

Although many of his songs pay homage to the city where he grew up, “65th and Ingleside” is the most upbeat, hopeful entry.

The song narrates Chance’s love for his partner as she stayed by him during his struggled with addiction and mental illness.

The lyrical emblem of this relationship, with all its heartbreak and hope, is the intersection where Chance lived with his partner early in their relationship: at 65th Street and Ingleside Avenue on the East Side.

4. “Someday We’ll Go All The Way” By Eddie Vedder

Illinois isn’t just a place to find seas of rolling golden grain—it’s also home to several iconic sports franchises. 

For a long time, one of the most unfortunate of these franchises was the Chicago Cubs, the baseball team that experienced the most infamous championship drought in the history of professional baseball.

The team spent 108 years attempting to win a World Series, and that struggle is the subject of Eddie Vetter’s radiant ode “Someday We’ll Go All The Way.”

With its boundless, tender optimism, the song is a tear-jerker for any Cubs fan. And when the Cubs finally won their World Series in 2016, it transformed from an ironic ballad to an awe-inspiring celebration.

5. “Lookin’ Out My Back Door” By Creedence Clearwater Revival

The next song on our list is “Lookin’ Out My Back Door” by Creedence Clearwater Revival. Alongside “Fortunate Son” and “Born on the Bayou,” this song ranks as one of the most famous entries in CCR’s discography, and like those songs, its subject is pure Americana.

Illinois is only mentioned twice in the song: at the beginning, the narrator recounts that he just got back, and at the end, he says he’ll be returning—signaling Illinois’ place as a crossroads in American culture.

In between these two lines, the song is a hoot and a half, depicting the narrator as he looks out his titular back door to discover that a circus has taken up residence.

While it isn’t the timeless ode that Stevens or Fiasco offer, CCR’s “Lookin’ Out My Back Door” nonetheless belongs on a list of classic Illinois tunes.

6. “Johnsburg, Illinois” By Tom Waits

Illinois is a big state, and there’s an abundance of human life and love that stretches beyond the bounds of Chicago.

One such place is Johnsburg, Illinois, a town immortalized by Tom Waits in the song of the same name.

The song is a beautiful tribute to Waits’s wife, Kathleen Brennan. Its poetic lyrics entwine the geography in Illinois with that of Waits’s body: in one line, he mentions his wife’s name tattooed on his arm, and in another, he mentions the rural Illinois farm where she grew up. 

Ultimately, he sends up Brennan’s upbringing with a short and sweet reference to the town: “She grew up outside McHenry / in Johnsburg, Illinois.” A timeless love story if we’ve ever heard one.

7. “Homecoming” By Kanye West

Rapper Kanye West has seen it all, from international acclaim to his sensitive lyrics and refined production to critical scorn and public controversy amidst his turbulent personal life.

But nothing can beat old-school Kanye, and his best old-school Chicago track is “Homecoming,” from the hit album Graduation.

Featuring a hook from Coldplay member Chris Martin, “Homecoming” addresses Kanye’s tender relationship with the city where he grew up.

He personifies Chicago as a woman named Windy, who both encourages him in his musical pursuits and admits to having a darker side

Ultimately, the song is a moving attestation of one of West’s enduring themes—the dream of going home again. We think there’s no better song about Illinois than that.

8. “100 Chicagos” By Lupe Fiasco

Though he hasn’t achieved the same level of global fame as others on this list, Lupe Fiasco is one of the most talented voices in contemporary rap and hip-hop.

Much of his music alludes directly or indirectly to his hometown of Chicago (such as “Kick Push,” a song about skateboarding in the Chicago area), but his most Illinois-centric tune is “100 Chicagos.”

The song is both a testament to Fiasco’s love for his home city and a vivid portrait of his unstable upbringing. It is dotted with references to Chicago landmarks and elements of the West Side, where Fiasco was raised until the age of ten.

9. “2120 South Michigan Avenue” By The Rolling Stones

Our ninth song, “2120 South Michigan Avenue,” has a somewhat dubious distinction: it is the only song on this list that does not have any lyrics.

You might be asking, “No lyrics? How can a song be about Illinois if it doesn’t have any lyrics?”

Well, dear reader, this is a book that you can judge by its cover—or at least its title. 2120 South Michigan Avenue was (and still is) the street address of the recording studio where the Stones recorded this song and others on their second EP, Five By Five.

The connection might seem tenuous at first, but as you listen, it becomes clear that with its bluesy energy, the song could only have come out of the place that spawned Chicago blues.

10. “My Kind Of Town” By Frank Sinatra

As mentioned earlier, Sinatra loves to croon about the Prairie State, and the second of his famed love song to it is “My Kind Of Town.” Here, our singer gushes over the special feeling that you can’t help but feel in Chicago. 

The people, the music, the sights, the atmosphere—Sinatra leaves no stone unturned when he highlights just what Chicago has to offer

This song is just what every Chicago local needs to hear every now and then to remind themselves of the beauty of their home state.  

Summing Up Our List Of The Best Songs About Illinois

As you can see, there’s something about Illinois that just lends itself to great music. Maybe it’s the wide-open spaces or the Midwestern values and spirit, but there are some amazing songs about the Prairie State.

But these ten entries represent just a sample of the amazing music that Illinois has inspired, and there are surely more to be written.

Let us know if there’s another song we missed.

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Laura has over 12 years experience teaching both classical and jazz saxophone and clarinet. She now resides in California where she works as a session and live performer.