The three white stripes 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 stripes represents the South Branch of the Chicago River and the Great Canal. Finally, the four red stars on the center white stripe represent, from left to right, Fort Dearborn Massacre, the Great Chicago Fire, the World Columbian Exposition, and the Century of Progress Exposition.
In addition, each of the six points of the stars stand for a value of the city:
- On the Fort Dearborn Massacre star (added in 1939): transportation, labor, commerce, finance, populousness, and salubrity.
- On the Great Chicago Fire star (on the 1917 flag): religion, education, esthetics, justice, beneficence, and civic pride.
- The points on the World Columbian Exposition star (on the 1917 flag) represent political entities Chicago belonged to: France 1693, Great Britain 1763, Virginia 1778, the Northwest Territory 1798, Indiana Territory 1802, Illinois 1818.
- The Century of Progress star (added in 1933: World's Third Largest City, City's Latin Motto (Urbs in horto - City in a garden), City's "I Will" Motto, Great Central Marketplace , Wonder City, Convention City.
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