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:

France 1693

Great Britain 1763

Virginia 1778

Northwest Territory 1798

Indian Territory 1802

Illinois Statehood 1818

The Second Red Star represents the Chicago Fire of October 8-10, 1871.

The Points of the Second Red Star Signify:

transportation

labor

commerce

finance

populousness

salubrity

The Third Red Star represents the World's Columbian Exposition of 1893.

The Points of the Third Red Star Signify History of the Area:

religion

education

esthetics

justice

beneficence

civic pride

The Fourth Red Star represents the Century of Progress Exposition of 1933 (added in 1933).

The Points of the Fourth Red Star Signify: