From "Curbed Chicago"
Each star commemorates an important moment or structure in the city's history, and each point on each star has a meaning. Local artist Phil Thompson of Cape Horn Illustration has paid homage to the city's flag by creating a new series of images that dives into the history and meaning of each star.
A fan of Chicago architecture and history, Thompson has previously (and painstakingly) illustrated the common architectural styles of homes found in Chicago as well as the homes of some of Chicago's most famous residents. Thompson has changed gears on his latest series and instead of illustrating homes, he has turned his attention to the city's famous flag.
In order, the stars on the flag represent Fort Dearborn, the Great Chicago Fireof 1871, the Columbian World Exposition in 1893 and the Century of Progress exposition in 1933.