Chicago's Steve Goodman (1948-1984) wrote and recorded "City of New Orleans" for his first album, released in 1971. In an often told story, Goodman encountered Arlo Guthrie at the bar in The Quiet Knight (where Guthrie was the headliner) and asked to play a song for him. Guthrie was standoffish, telling Goodman that he would have to buy him a beer, and that Guthrie would listen only until he finished drinking. The result was a number four hit for Guthrie in 1972 (his only cut to make the Top 40), and later a number one hit for Willie Nelson in 1984, with dozens of covers in between and since.
Goodman was born and grew up in Chicago's Albany Park neighborhood, and attended high school in Park Ridge, where he was a classmate of Hillary Rodham. I am pretty sure that he lived in Evanston at some point, or at least hung out here, probably at the Amazing Grace coffee house and performance space. He briefly attended the University of Illinois in Urbana-Champaign, traveling back and forth on the Illinois Central (the song, however, was inspired by a longer trip to visit his wife's family). He was diagnosed with leukemia in around 1968 and died in 1984 at age 36. He won a posthumous Grammy in 1985 for the Willie Nelson release.