Chicago

Chicago is a semi-autobiographical road trip: a young man travels with a friend in a van. Stevens said he had had exceptional and traumatic experiences in Illinois, visiting Chicago at a hard time and being pulled over by police outside Peoria, but warned against confusing the songs' first-person voice with his own. It draws on Carl Sandburg's poem Chicago and builds from strings and trumpet to a full choir on the refrain about all things going. Petrusich called its lines about crying in the van for freedom gut-punching.

He has recorded it five ways, including an acoustic version and an easy-listening arrangement nearly used on the album, and a 2004 demo issued in 2016. Little Miss Sunshine made it widely known, and it later became the opening theme of Netflix's The Politician, which is why the official audio in the hypersongs web was posted in 2019. It went gold, gave the All Things Go festival its name, and is his most performed song by far. Japanese Breakfast covered it in Chicago in 2023.