Songs About Chicago

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Some time ago I did a list of songs based on place names and an online acquaintance told me off for not including her home town on the list – Chicago. I said I would make up for it because I knew there were a few good tracks about Chicago.

She reminded me of that last week. I hadn't done it. Oops!


I haven't been to Chicago. My knowledge of the place comes from television and movies. I can't even think of too many books I've read that have been set there. I know a bit about some incidents in the 1960s that occurred there; I have heard of the Chicago Bulls and have watched the Chicago Bears. I do know about Chess Records and the Chicago blues scene. In fact, that is probably the only thing about Chicago I think I have some genuine knowledge of.

So, let's see if these ten songs can help educate me! Rules: one song per artist (which really only affects Sinatra), one version of each song, songs I like, songs about Chicago (not just used by sports teams), and that's it. There is nothing here from the musical; I saw it live once 20 years ago and remember very little about it, so apologies there.

Chicago songs!
'Little Joe From Chicago' by The Nat 'King' Cole Trio (1940-ish)

Fun piano-led jazz tune from the early years of Cole's career, this song is one I have on a compilation album and I can find very little about it. Still, I like this one.
'My Kind Of Town' by Frank Sinatra (1964)

Sinatra had a few songs about Chicago, but this is the one I prefer. The build-up and the fact that Sinatra sounds like he means it, and is not just singing someone else's words, which is something I get the impression of from a lot of his 1960s work onwards, sells it to me.
'Chicago' by Graham Nash (1971)

Probably better known from the live version by Crosby, Stills, Nash & Young, the original was from Nash's first solo album. It was about the trouble at the 1968 Democratic Convention in Chicago, so it was actually a protest song 3 years after the event. But that is a really good and hopeful chorus.
'Jesus Just Left Chicago' by ZZ Top (1973)

This boogie-blues track is, I think, just an excuse for Billy Gibbons to have fun with an extended guitar solo, and it's worth it. This is some fine playing from a band that was already tight so early in their career.
'The Night Chicago Died' by Paper Lace (1974)

Written by some British songwriters (which is obvious because one of the areas they mention is actually in the bay), this track tells the story of Al Capone in the 1930s through the medium of a chipper, upbeat song that is weird to sing along to.
'Sweet Home Chicago' by The Blues Brothers (1980)

Yes, I know this song was done by many blues artists beforehand, but I really do enjoy this version from the soundtrack of one of the best movies of the 80s . The whole band just plays so well, making this a wonderful blues track.
'Chicago' by Luther Allison (1987)

The 1987 album Rich Man was a fine blues album in the midst of 80s pop, and so it didn't really make much of an impact. Shame, because the whole album is good, and this track is no exception.
'Back To Chicago' by Styx (1990)

Apparently, it is accepted that people who like music don't like Styx. I don't know why because they have released some really good songs. Having said that, the album Edge Of The Century is not one of their strongest, yet this track is one of the better from the collection.
'Chicago (Chi-Town) Blues' by Earth, Wind And Fire (1993)

I got this album thinking it was a greatest hits package "back in the day", but it is an actual studio album. In fact, they've been releasing albums into this century. But this album was really good and I thought it was a bit of fun.
'Wasn't Born In Chicago' by Gary Moore, Cass Lewis and Darrin Mooney (2003)

And we finish with modern blues by the late, great Gary Moore and friends. Another song that is an excuse to have a guitar solo of sublime beauty; the album it comes from (Scars) is an under-rated gem.
And there we are, ten songs about Chicago. The town is the home to a very specific style of blues music, and yet so many others have also joined in celebrating the place. You might notice a lack of modern "r&b" and hip-hop, despite some songs being about the place… sorry, but I don't like any of the ones I've heard or have in various compilation albums.

Still, I reckon this a really fine list of music.
via GIPHY

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