The song has been recorded by many artists, but the best-known versions are by Frank Sinatra, Ben Selvin and Judy Garland.

The song alludes to the city's colorful past, feigning "... the surprise of my life / I saw a man dancing with his own wife", mentioning evangelist Billy Sunday as having not been able to "shut down" the city, and State Street where "they do things they don't do on Broadway".

The song made a minor appearance on the U.S. pop charts, reaching #84 in the fall of 1957.

The original third verse included the lines, "More Colored people up in State Street you can see,/ Than you'll see in Louisiana or Tennessee" and makes reference to the Chicago Stockyards.

Later recordings have a number of replacements: Of all versions, Judy Garland's 1961 Judy at Carnegie Hall concert recording contains more references than most: Marshall Field's department store, the Drake Hotel, the Chicago Loop, The Pump Room at the Ambassador East hotel, and even Mrs O'Leary's Cow.