The Meaning of Wilco’s “Via Chicago”

Wilco press photo from 1996, taken in NYC. Photo by Ken Weingart/Michael Ochs Archives/Getty Images.

“Via Chicago” is a song from Wilco’s 1999 album Summerteeth that has always stuck with me. While the album as a whole sounds a bit overdone, production-wise, “Via Chicago” is truly something else. In terms of emotional weight, “Via Chicago” is the best song on Summerteeth, and perhaps one of the best all-time Wilco songs.

Lyrically, “Via Chicago” is quite the enigma. The opening lines, “Dreamed about killing you again last night / And it felt alright to me” grab your attention right away, and from there Jeff Tweedy drops poetic verse after poetic verse about this mysterious dream, in relation to this longing to go back home.

With Tweedy addressing them as “you”, one would assume that he is singing about another person, perhaps someone that he misses but whom he maybe doesn’t have the best relationship with anymore. The fact that the song’s meaning is not clear, however, even after countless listens and careful readings of the lyrics, suggests that Tweedy is not singing about another person at all. He’s singing about himself, or an alter-ego of himself that he doesn’t like very much.

The song starts out peaceful, with an acoustic guitar and Tweedy’s solemn voice, while layers of drum and piano are gradually added. As Tweedy continues to sing about the darkness inside his soul, the veil of sanity in the musical arrangement gradually fights its way through until the song reaches a chaotic peak about three minutes in, with everything descending into distortion and Tweedy shouting out the tension-releasing lyrics: “I rest my head on a pillowy star / And a cracked door moon / That says I haven’t gone too far.”

Wilco live at Brooklyn Steel in October 2019. Photo by Anthony Bauer.

At the time that “Via Chicago” was written, Jeff Tweedy was very much a tortured artist. He had been struggling with migraines his whole life and found relief in painkillers, and soon he found himself with a nasty opiate addiction. With this knowledge it can be assumed that the final verse is some sort of reassurance to himself, that he can still have his life back, if he can only get home and find some peace and quiet.

Alternatively, he will end up like the “Man with a face like mine / Being chased down a busy street,” in a bad way and in trouble with the law. He imagines watching it on TV from the safety of his home, rather than being the guy involved in the actual trouble. “And when he gets caught I won’t get up / And I won’t go to sleep.” He’ll stay right there on the couch and watching the scenario play out will not affect him because it won’t involve him directly.

Listening to “Via Chicago” a few times you might notice that the guitar distortion they’re using kind of sounds like a train coming into the station, with the loud banging distortion representing the train car stopping. This would fit well with the song’s title, which brings to mind the image of a train station or airport. Tweedy himself has even said the distortion here was how the band imagined it might sound if you were standing under Chicago’s “L” train and trying to have a conversation.

“Via Chicago” is an example of the type of song that makes Wilco such a great band. This chaotic distortion first entered their repertoire with “Misunderstood” off 1996’s Being There, and has continued to be a staple in their sound even in modern times. Of course this idea of chaos coupled with ambiguity was expanded upon, and some might say perfected on their following album, 2001’s Yankee Hotel Foxtrot.

There is a fantastic live version of “Via Chicago” that comes from Wilco’s 2005 live album Kicking Television. They really go all in on the distortion there, and it becomes much more intense, making the eventual release of tension that much more satisfying.

Listen to “Via Chicago” by Wilco below.

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