The 3 White stripes:
Top White Stripe represents the North side of the city.
Center White Stripe represents the West side of the city.
Bottom White Stripe represents the South side of the city.
The 2 Blue stripes:
Top Blue stripe represents Lake Michigan and the North Branch of the Chicago River.
Bottom Blue stripe represents the South Branch of the Chicago River and the Great Canal.
The 4 Red stars on the Center White Stripes represent something as well as each of the points on the stars themselves:
The First Red Star represents Fort Dearborn (added in 1939).
The Points of the First Red Star Signify:
The Second Red Star represents the Chicago Fire of October 8-10, 1871.
The Points of the Second Red Star Signify:
The Third Red Star represents the World’s Columbian Exposition of 1893.
The Points of the Third Red Star Signify History of the Area:
Great Britain 1763
Northwest Territory 1798
Indian Territory 1802
Illinois Statehood 1818
The Fourth Red Star represents the Century of Progress Exposition of 1933 (added in 1933).
The Points of the Fourth Red Star Signify:
World’s Third Largest City
City’s Latin Motto
I Will Motto
Great Central Market
~The Meaning of Chicago’s Flag