And okay, given that this is a train journey and Chicago is at the core of it, how on earth can I not play Steve Goodman's great song, "The City of New Orleans"??! Yes, I know "New Orleans" is in the title, but that train departs (or arrives, depending on your direction) from Chicago. (In the song, it departs from Chicago, going "southbound." It was on the Illinois Central line, and as one of the lines says, "The train pulled out at Kankakee," which is a town about an hour or so southwest of Chicago.
I have a couple of versions here.
The first, of course, is from Steve Goodman, recorded in 1972. Arlo Guthrie has a terrific version, and made the song famous, which Steve Goodman also credited. Willie Nelson won a Grammy for it. But this is how the song is done --
This second video is not from Arlo Guthrie or Willie Nelson. Nor the wonderful version by The Highwaymen -- Nelson, Wayland Jennings, Johnny Cash and Kris Kristofferson. (Little known fact: John Cash was the first person offered the song, but he turned it down. And spent the next several decades saying it was one of he great regrets. But on a TV special he invited Steve Goodman on to sing the song. By the way, he didn't turn it down because he didn't like it -- he thought it was wonderful. But he'd recorded SO many train songs, he didn't want to keep being identified with them alone.)
Instead, this is performed by Jimmy Buffet, and is fairly similar to Goodman's original. Which isn't surprising since he and Steve Goodman were very close, and even collaborated on songs. In fact, when Steve Goodman passed away shortly before his beloved Chicago Cubs finally made the post-season in 1984 for the first time in 39 years, he had been scheduled to sing the National Anthem before the first game of the playoffs at Wrigley Field...and Jimmy Buffet sang it his place. Which makes this performance all the more touching.
This version takes place in the right field bleachers of Wrigley Field, when Jimmy Buffet was the first person ever to give a concert there, in 2005. It's a nicely-edited video...and this is how he ended the concert --