Two blue bars, four red six-pointed stars, white in between — and an unusual number of people in this city can actually explain what at least one of those stars means. The real story has a name attached, and that name is Wallace Rice.
A writer wrote the rules, then won his own contest
In 1917, Chicago's Municipal Flag Commission ran a public design competition for an official city flag. Wallace Rice — a writer and Art Institute of Chicago lecturer — was initially brought on to help write the contest's rules. He then entered his own design, and it won. The City Council adopted it that spring, and while sources differ on the exact date, it's commonly given as late March or early April 1917. Chicago didn't actually have an official flag before this — one more thing the city got around to doing on its own schedule, by its own design, rather than waiting for convention.
Why the stars have six points, not five
Rice's choice to give the stars six points instead of the more familiar five was deliberate. Five-pointed stars are the standard for sovereign nations and U.S. states, and Rice didn't want Chicago's flag mistaken for anything bigger than it was trying to be. He called the resulting shape "peculiarly and singularly a Chicago star" — which, whether or not that was strictly true in 1917, has turned out to be true now. A six-pointed red star on a white field reads as Chicago and nothing else, on a tattoo, a hat, a bar's neon sign, or a t-shirt three states away.
What the bars and stripes mean
Rice's own 1917 description called the two blue bars "the color of water" — standing for Lake Michigan and the Chicago River. The three white stripes between and around them have come to represent the city's geography: the North, West, and South Sides, top to bottom. (Rice's original writeup also gave the design a grander, more nationalistic meaning — the blue bars as the Atlantic and Pacific coastlines, the white stripe in the middle as the country's center — but the Chicago-specific "three sides of the city" reading is the one that actually stuck and gets taught today.)
Four stars, and only two with an official meaning
The flag didn't start with four stars. Rice's original 1917 design had two, and the other two were added later — one in 1933, one in 1939. Today they're generally understood to represent, in order: Fort Dearborn (the fort whose 1812 destruction is tied to the city's earliest colonial-era history), the Great Chicago Fire of 1871, the World's Columbian Exposition of 1893, and the Century of Progress World's Fair of 1933. Worth knowing: only the meanings of the first two stars are actually preserved in official City Council records. The third and fourth star's meanings are the ones everyone has simply agreed on over time — accurate, well-documented events, just not technically "official" the way the first two are.
The fifth star that's never happened
Chicagoans have spent decades informally lobbying for a fifth star, and none of the campaigns have ever gone anywhere official. People have pitched one for the city's 2016 Olympic bid (lost to Rio de Janeiro), for the Special Olympics (which was founded in Chicago), and, most recently, Mayor Lori Lightfoot floated one in May 2020 to mark the city's COVID-19 response. The Chicago History Museum has run an ongoing exhibit letting the public vote on fifth-star ideas. The one every Cubs fan brings up is the 2016 World Series, which broke a 108-year championship drought — a genuinely flag-worthy Chicago moment that, as of this writing, is still only unofficial.
Want the other stories behind it? The second star and the third both have their own full write-ups.
We put this same six-pointed star on a real trucker hat — not a logo slapped on a blank, the actual flag, wearable. Every one sold helps keep this a two-person, walk-it-yourself operation.
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