Watch The Oldest Footage of Chicago on Film

The footage features one of Chicago’s deadliest disasters—and cameos from Theodore Roosevelt and Al Capone.

SS ‘Eastland’ overturned in the Chicago River.
SS ‘Eastland’ overturned in the Chicago River. / Library of Congress/GettyImages

What did Chicago look like at the turn of the last century? Yestervid, a video series showcasing film compilations, answered that question by dredging up some of the oldest footage of the Windy City known to exist. The scenes in this five-minute-long video showcase the lakeshore, city streets, stockyards, baseball games, and more circa the early 1900s. Spoiler: There were a lot more cows. 

A handy split-screen with a map pinpoints the approximate location and date of the footage, a useful tool for anyone who wants to compare their own visuals of Chicago to the urban views from yesteryear. While most of the footage comes from around 1915, there’s also an audio recording from way back in 1893.

The video features footage from the aftermath of the Eastland disaster, which occurred on July 24, 1915. Employees of the Western Electric Company boarded the SS Eastland for the company’s annual picnic; the passenger liner—which had a reputation for being unstable—began listing and was righted several times before ultimately capsizing, killing 844 people. According to Britannica, “hundreds more lives were lost in the Eastland disaster than in the Chicago fire of 1871.” In another part of the video, you’ll spot former president Theodore Roosevelt riding through the city in 1917 (he was there to urge military preparedness in the face of World War I) and notorious gangster Al Capone in 1931.

To add to the list of discoveries, the producers believe they have identified the location of the oldest surviving film of the city, a few shots of a police parade from 1896. The building in that film has been demolished, but Yestervid pinpoints the location as the corner of Michigan Avenue and Monroe Street downtown.

Check out the footage above—and if you can’t get enough of videos from eras past, watch this footage of New York City in the 1970s and this colorized video of life in Victorian England.

A version of this story ran in 2015; it has been updated for 2023.