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About the municipal flag of Chicago

The municipal flag of Chicago consists of two blue horizontal stripes on a field of white, each stripe one-sixth the height of the full flag, and placed slightly less than one-sixth of the way from the top and bottom. Between the two blue stripes are four red, six-pointed stars arranged in a horizontal row. The three sections of the white field and the two stripes represent geographical features of the city, the stars symbolize historical events, and the points of the stars represent important virtues or concepts.

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. The lighter blue on the flag is variously called sky blue or pale blue; in a 1917 article of a speech by Rice, it was called "the color of water".

There are four red six-pointed stars on the center white stripe. From left to right:

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, since 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' second largest city (became third largest in a 1990 census when passed by Los Angeles); 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.