Songs About

Songs About Chicago

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

  1. 1

    Sweet Home Chicago by Robert Johnson 1936

    The blues standard the whole city claims.

  2. 2

    My Kind of Town by Frank Sinatra 1964

    Sinatra tipping his hat to Chicago.

  3. 3

    Chicago (That Toddlin' Town) by Frank Sinatra 1957

    A bright, brassy postcard of the city.

  4. 4

    Lake Shore Drive by Aliotta Haynes Jeremiah 1971

    The road along the lake, turned into a local hymn.

  5. 5

    Bad, Bad Leroy Brown by Jim Croce 1973

    The baddest man on the whole South Side.

  6. 6

    Go Cubs Go by Steve Goodman 1984

    What Wrigley Field sings after every win.

  7. 7

    Via Chicago by Wilco 1999

    A dreamlike, unsettled trip back home.

  8. 8

    Chicago by Sufjan Stevens 2005

    A road trip and a search for something more.

  9. 9

    Homecoming by Kanye West 2007

    The city itself cast as an old hometown love.

  10. 10

    Take Me Back to Chicago by Chicago 1977

    The band paying tribute to its namesake.

  11. 11

    The Night Chicago Died by Paper Lace 1974

    A pop tall tale of gangland shootouts.

  12. 12

    Chicago by Graham Nash 1971

    A protest call tied to the city's 1968 trial.

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