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Stripes The three white background areas of the flag represent, from top to bottom, the North, West and South sides of the city. The top blue stripe represents Lake Michigan and the North Branch of the Chicago River. The bottom blue stripe represents the South Branch of the river and the "Great Canal", over the Chicago Portage.

Stars There are four red six-pointed stars on the center white stripe, from left to right (although this is not the order in which they were added to the flag).

The first star represents Fort Dearborn. It was added to the flag in 1939. Its six points symbolize transportation, labor, commerce, finance, populousness, and salubrity. The second star stands for the Great Chicago Fire of 1871, and is original to the 1917 design of the flag. Its six points represent the virtues of religion, education, aesthetics, justice, beneficence, and civic pride. The third star symbolizes the World's Columbian Exposition of 1893, and is original to the 1917 design. Its six points stand for political entities Chicago has belonged to and the flags that have flown over the area: France 1693, Great Britain 1763, Virginia 1778, the Northwest Territory 1789, Indiana Territory 1802, and Illinois (territory 1809, and state 1818). The fourth star represents the Century of Progress Exposition (1933–1934), and was added in 1933. Its points refer to bragging rights: the United States' 2nd Largest City, Chicago's Latin Motto (Urbs in horto – City in a garden), Chicago's "I Will" Motto, the Great Central Marketplace, Wonder City, and Convention City. A possible fifth star has been proposed for the city flag on more than one occasion. The first occasion occurred in the 1940s, when a letter to the Chicago Tribune asked that a fifth star be added to the city flag in honor of the city's place in the history of the nuclear age. On another occasion, a star was proposed in honor of Harold Washington, the first African-American mayor of Chicago.[4] A fifth star was also discussed following the Chicago Flood of 1992. A proposal was put forward by the 2016 Olympic Games Bid Committee; if the bid to host the games had been successful, a fifth star might have been added to the flag; however, the Olympic bid was lost to Rio de Janeiro.