Similar to our mantra to use the architecture of our cityscape to tell Chicago history, I decided to search for historic songs about Chicago that could tell the story of Chicago history. Like Chicago architecture, popular culture and its music can be our history books.

It would be easy to list countless songs with Chicago in their title or mere references to this great city, like “Sweet Home Chicago,” which is the first that comes to mind for many. These songs about Chicago contain very little of Chicago history in them however. Any basic search for the lyrics of Chicago songs will deliver more about the band than the history of the city.

So I headed to the Special Collections of my alma mater of the University of Illinois at Chicago to see what historic songs about Chicago I could find. In their Chicago sheet music file, I uncovered dozens of songs, mostly marches inspired by the world’s fairs and other instrumental two-steps and fox trots.

Political Propaganda in Historic Songs About Chicago

Then I came across not one but two pieces of mayoral propaganda for William Hale Thompson. My favorite of the two is called “Big Bill the Builder” from 1928. The song lyrics champion Thompson, our last Republican mayor, for being Chicago’s favorite son. His work on the Chicago Waterway and his stance against the draft are cited along with other national claims. The song puts Thompson’s name alongside the likes of George Washington, pointing to Thompson’s hope for a presidential candidate nomination from the Republican Convention that same year.

Of course in this song about Chicago there is no mention of the Race Riot of 1919 or the St. Valentine’s Day Massacre, both of which happened during Big Bill’s terms. It’s a rosy picture compared to his “moronic buffoonery, barbaric crime, triumphant hoodlumism, unchecked graft, and a dejected citizenship,” according to the Chicago Tribune. Luckily, this song is just about as remembered as the embarrassing ode to Chicago by Umphrey McGee from just a couple years ago.

“A Hot Time in the Old Town Tonight”

On a more popular note, songs about Chicago can come in all forms. Let’s take, for example, “There’ll Be a Hot Time in Old Town Tonight,” written in 1896.

This ragtime song from the late 1800s, written by Joe Heyden, was not originally a song about Chicago. It has been reworded into a song about Chicago, however, to include the following lyrics:

“Late one night, when we were all in bed.

Mrs. O’Leary lit a lantern in her shed.

Her cow kicked it over,

Then winked her eye and said,

‘There’ll be a hot time in the old town tonight!’ ”

The change is an easy one, not to mention catchy. The cow version is performed at Chicago Fire games and played by marching bands around Illinois. It’s the state’s sort of unofficial fight song. This adoption of Mrs. O’Leary’s story into the song shows the prevalence of the Great Chicago Fire throughout our city’s history and how fun it can be to tell history through a song.

– Elizabeth Tieri, Chicago Detours Tour Guide