The crossword solution for the term 'Chicago, in a song' is 'TOWN', with four letters. Chicago is a major city in the United States, located in the state of Illinois. It is the third most populous city in the United States and has been featured in many songs over the years. Some of the most popular songs about Chicago include 'Sweet Home Chicago' by Robert Johnson, 'Saturday in the Park' by Chicago, and '25 or 6 to 4' by Chicago.