It starts with those trumpets. You know the ones. They feel like a sunrise over a highway, specifically I-94, and suddenly you’re six minutes deep into a song about a road trip that isn't really about a road trip at all. Chicago by Sufjan Stevens lyrics have this weird, magnetic way of making you feel nostalgic for a life you never actually lived. Or maybe you did live it. Maybe you were the one driving a van across state lines with nothing but a map and a massive amount of emotional baggage.
Honestly, it’s a lot to take in.
The song dropped in 2005 on Illinois, which was supposed to be part of this ambitious "50 States Project." Sufjan later admitted that the whole 50-state thing was kind of a promotional gimmick, but the music he produced during that era was anything but a joke. "Chicago" is the centerpiece. It’s the heart. It’s a messy, soaring, choir-backed confession that manages to be both tiny and universal at the exact same time.
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The Narrative Arc of a Total Disaster
Most people think "Chicago" is a celebration of the city. It’s really not. If you actually look at the Chicago by Sufjan Stevens lyrics, the song is a chronicle of a series of failures. He’s moving things. He’s losing things. He’s making a "lot of mistakes."
It’s about the reckless, often stupid optimism of youth.
The protagonist—which we assume is Sufjan, though he often weaves fiction into his semi-autobiographical work—is traveling from Michigan to Chicago, then eventually to New York. There’s a van involved. There’s a "lot of things" he’s brought along, both physical and psychological. When he sings about crying in the van or his friend being "a little bit drunk," he isn't trying to be poetic. He’s being literal. It’s that specific brand of indie-folk realism that makes the song feel like a grainy Polaroid found in a thrift store.
Vulnerability is the engine here.
You’ve probably felt that specific type of desperation where you think changing your zip code will magically fix your personality. "I fell in love again / All things go, all things go." This refrain is the soul of the track. It’s a mantra of radical acceptance. You lose the girl, you lose the van, you lose your mind, but the world keeps spinning. The repetition isn't just for a catchy hook; it's a way of self-soothing.
Why the "All Things Go" Refrain Matters
Sufjan is a master of the repetitive phrase. In "Chicago," the phrase "all things go" is borrowed, at least in spirit, from Carl Sandburg’s poetry—Sandburg being the definitive poet of Chicago. But Sufjan gives it a spiritual, almost Buddhist twist.
Think about the structure:
- It’s a rhythmic anchor.
- It acknowledges the transience of grief.
- It validates the "mistakes" mentioned earlier in the verse.
When he sings about driving to New York or selling his shoes, he’s describing a person in the middle of a manic shift. We've all been there. Maybe you didn't sell your shoes to get to Brooklyn, but you’ve definitely made a choice that felt like a "great design" at the time, only to realize later it was just a byproduct of being twenty-something and confused.
The Production is a Layered Mess (In a Good Way)
Musically, the song is a maximalist dream. You have the vibraphone, the string section, the brass, and that persistent, driving beat. It feels like a train. It feels like progress.
But look at the lyrics again.
"I made a lot of mistakes." He says it over and over. Usually, when a songwriter admits to making mistakes, they do it in a slow, sad ballad. Sufjan does it over a jubilant, orchestral explosion. This creates a cognitive dissonance that defines the "Sufjan Sound." You’re dancing, but you’re also kind of mourning your past self.
It’s worth noting that the "Adult Contemporary" version of the song—the one famously used in the opening credits of The Politician or in the movie Little Miss Sunshine—strips some of that raw indie energy away, but the lyrical weight remains. Whether it’s the original seven-minute epic or a radio edit, that confession about the "van" and the "drunk friend" remains the grounded reality of the piece.
Let's Talk About the "Great Design"
One of the most debated lines in the Chicago by Sufjan Stevens lyrics is: "I had a great design / I had a great design."
What is the design?
Is it an architectural plan for his life? Is it a reference to God? Sufjan’s work is famously shot through with Christian themes, though he’s never been a "Contemporary Christian Music" artist in the traditional sense. In this context, the "great design" feels like the hubris of a young artist. He thought he had it all figured out. He thought the trip to Chicago was part of a grander destiny.
The irony, of course, is that the "design" failed. He ended up crying in a van.
This is where the song connects with anyone who has ever had a five-year plan fall apart by year two. The beauty isn't in the design itself; it's in what happens after the design fails. You keep driving. You keep going to New York. You keep falling in love again.
The Cultural Impact of 126 BPM
Twenty years later, why do we still care?
Music critics like Pitchfork’s Mark Richardson pointed out early on that Illinois was an exercise in "extravagant empathy." "Chicago" is the peak of that. It’s a song that shouldn't work. It’s too long, it’s too earnest, and it has too many instruments. But it works because it refuses to be cynical.
In a world of irony-poisoned music, Sufjan Stevens stood up and said, "I felt everything, and it was a mess, and that’s okay."
People use this song for everything now.
- Road trip playlists (obviously).
- Coming-of-age movie montages.
- Late-night existential crises.
It has become a shorthand for "the journey." Not the fun, Instagram-filtered journey, but the real one where you’re tired and your shoes are gone and you’re wondering if you’re actually a good person.
The Geography of the Lyrics
Sufjan is very specific about his locations.
- Chicago: The destination of hope.
- New York: The destination of escape.
- The Van: The liminal space where the actual growth happens.
By naming these places, he anchors the abstract feelings of the lyrics in a physical reality. It makes the "mistakes" feel more tangible. They aren't just metaphors; they happened at a specific mile marker on the highway.
How to Actually Listen to Chicago
If you want to get the most out of the Chicago by Sufjan Stevens lyrics, don't just put it on as background noise while you’re doing dishes.
Listen to the "Multiple Personalities" version. Listen to the demo. You’ll hear how the song evolved from a simple acoustic thought into this towering monument of sound. You’ll notice the way his voice cracks slightly when he hits the higher register on "I fell in love again."
That crack is where the truth is.
It’s the sound of someone realizing that "all things go" isn't just a catchy phrase—it's a law of the universe. People leave. Vans break down. Cities change. You change.
Practical Ways to Engage with the Lyrics Today
If you're looking to dive deeper into the world Sufjan created, there are a few things you can do to really "get" the song in 2026.
- Read Carl Sandburg's Chicago Poems: Specifically "Chicago" (1914). You’ll see exactly where Sufjan got his inspiration for the "City of the Big Shoulders" vibe. It adds a layer of historical grit to the indie-pop sheen.
- Track the "All Things Go" Sample: Look up how modern artists have sampled this specific line. Nicki Minaj’s song "All Things Go" is a direct emotional descendant, proving that Sufjan’s meditation on loss and family transcends the indie-folk genre entirely.
- Map the Route: If you’re ever in the Midwest, drive the stretch of I-94 from Michigan into the city. Play the song as the skyline appears. It sounds like a cliché, but there’s a reason thousands of people do it every year. The geography of the music matches the geography of the land perfectly.
- Analyze the "Seven Swans" Connection: To understand the spiritual weight of his lyrics, listen to his previous album Seven Swans. It provides the religious context that makes the "Great Design" line in "Chicago" feel much more heavy and intentional.
Ultimately, the song is a permission slip. It gives you permission to have messed up your life a little bit. It reminds you that "making a lot of mistakes" is just the entry fee for eventually being able to look back and say you actually lived. All things go, but the song stays. That’s the real great design.