This song is about the band missing their families and friends back in Chicago; everything reminds them of their problems and unfinished things that they miss on tour.
The backing vocals towards the end of the song: "Every blade of grass" is sung by Justin Pierre, the lead singer of Motion City Soundtrack.
Lead singer Patrick Stump, who also wrote the song, found out his bandmate Pete Wentz was a meticulous lyricist during the making of the album. Because of this, Stump was reluctant to allow the rest of the band to hear this tune, not wanting his work to be revised. "We had a huge fight over 'Chicago Is So Two Years Ago,'" he recalled in a 2013 interview with Alternative Press. "I didn't even want to record that song. I was being precious with things that were mine. Part of me was thinking the band wouldn't work out and I'd go to college and do some music on my own. I had a skeletal version of 'Chicago.' I was playing it to myself in the lobby of the studio. I didn't know anyone was listening. Sean [O'Keefe, producer] was walking by and wanted to introduce it to the others. I kind of lost my song. I was very precious about it. Pete didn't like some of the lyrics, so we had a big fight over that. We argued over each word, one at a time."
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