Chicago’s city flag was first designed in 1917. It is a classic flag design for a two reasons. One is that it’s a very clean design. But unlike any of the other flags, it is directly connected to Chicago’s people in a very unique way. Each of the stars represent an important point in Chicago’s history. The first 1917 design only had two stars on top. One of them represent the Great Chicago Fire of 1871 and another star represent the World Columbia Exposition of 1893. A third star was added in 1933 for the Century of Progress Exposition that opened that same year. The last star was added in 1939 to represent Fort Dearborn, now called Chicago. A fifth star has been proposed several times for various reasons including if the Cubs World Series title.