Chicago in Song

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Frank Sinatra may have sung it best with “This is my kind of town, Chicago is.” But don’t limit yourself to Ol’ Blue Eyes when celebrating Chicago with song, because the Windy City has endeared herself to a number of crooners.

You’ll find plenty of songs to fit whatever your mood.

There’s Sufjan’s Stevens hopeful “Chicago” and Kanye West’s infectious “Homecoming,” where he uses the metaphor of a former girlfriend to describe his love for his hometown.

There’s Jim Croce’s “Bad, Bad Leroy Brown” about a Southside Man who is the “baddest man in town” and Common’s “Southside.”

Elvis’ “In the Ghetto,” written by Mac Davis and covered in 1984 by Nick Cave  & the Bad Seeds, is about a young Chicago boy growing up in poverty.

Justin Townes Earl offered us a melancholy “Rogers’ Park” and Wilco gave us “Via Chicago.”

And finally, who doesn’t love Robert Johnson’s “Sweet Home Chicago” along with the Blues Brothers’ cover version?

Do you have a favorite song about Chicago? Let us know what it is! Check out the ones discussed here in our list, Songs About Chicago.