The Windy City runs deep through American music: blues from the South Side, Sinatra's swagger, indie love letters and one very loud Cubs anthem. Here is the set.
Updated 2026
Sweet Home Chicago by Robert Johnson 1936
The blues standard the whole city claims.
Chicago (That Toddlin' Town) by Frank Sinatra 1957
A bright, brassy postcard of the city.
Lake Shore Drive by Aliotta Haynes Jeremiah 1971
The road along the lake, turned into a local hymn.
Bad, Bad Leroy Brown by Jim Croce 1973
The baddest man on the whole South Side.
Take Me Back to Chicago by Chicago 1977
The band paying tribute to its namesake.
The Night Chicago Died by Paper Lace 1974
A pop tall tale of gangland shootouts.