Pop Songs
While Frank Sinatra might be associated the most with New York City, he also performed and enjoyed Chicago. He sang at the Palmer House from 1939 to 1942, and his cover of the 1922 song "Chicago (That Toddlin' Town)" is well known.
The title of this song reveals some high hopes for Chicago. The city was still in its early stages of growth, although trade and industry was starting to take off. What the writers of this song may not have known about was the Great Chicago Fire that would happen in October of 1871.
"Sweet Home Chicago" is a jazz song originally written in 1936. It's seen as one of the anthems of Chicago, and has been performed by many pop and blues artists. It can often be heard in sports arenas and bars across the city.