The six points on the third star of the Chicago Flag stand for the political entities that the land had belonged to since 1693.

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  1. France in 1693
  2. Great Britain in 1763
  3. Virginia in 1778
  4. the Northwest Territory in 1798
  5. Indiana Territory in 1802
  6. Illinois in 1818

(Of course this doesn't include the people who'd lived in the area for centuries before the Europeans came.)