The Flagpole Vol 5: A City That Wears Its Flag
The City of Chicago Flag
Right when I got off the plane, I saw it. A guy walking past me at O’Hare Airport with the Chicago flag tattooed on his calf: four red stars, two blue stripes, all crisp and bold against his pale skin.
I smiled. I hadn’t even made it to the bathroom, and already the city was showing its pride.
Not the actual tattoo I saw but a simple search reveals MANY similar interpretations.
Minutes later, I passed a gift shop overflowing with Chicago merch, most of it featuring the flag in one way or another. T-shirts, hats, mugs, baby onesies, even socks.
And it makes sense. The flag is distinctive, memorable, and just plain great-looking. When a well-designed flag meets a well-loved city, the result is magical.
The flag of Chicago features four red six-pointed stars between two horizontal blue stripes on a white background. The blue stripes represent Lake Michigan and the Chicago River, while the white spaces stand for the city’s North, West, and South sides. Each star marks a major event in Chicago’s history: Fort Dearborn, the Great Chicago Fire, the World’s Columbian Exposition (1893), and the Century of Progress Exposition (1933).
Over the next few days, I saw that same flag everywhere. Flying on city buildings, painted on underpasses, stitched into backpacks, baked into business logos, even at the United Center’s Shakedown Street before the Phish show.
It was on construction helmets, a bike messenger’s bag, and painted on dumpsters that somehow made even garbage collection feel like a source of civic pride.
I’ve always known about the Chicago flag. If you're a flag person (as you probably know by now, I very much am), it’s a legend. But seeing it in its natural habitat, so beloved and everywhere, made me think about flags a little differently. It wasn’t just a cool design (though it is that too). It was a symbol people carried because they felt something for the place it represented.
I didn’t go looking for inspiration, but it found me anyway. In a tattoo, a gift shop, a garbage truck. That’s the magic of a good flag. It sneaks up on you and says, let’s keep going.
It made me think about home. Denver actually has a great city flag. It’s bold, colorful, and meaningful, all the makings of a classic. But you wouldn’t know it. It’s rare to see it flying (except at my house), let alone on a T-shirt or someone’s calf. We’ve got the symbol. We just haven’t claimed it.
The City and County of Denver Flag- a blog post for another day…
Chicago reminded me that design is only half the story. The rest comes from people using it, wearing it, taking pride in it. I came home with a head full of new ideas, a few sketches on the plane, and the feeling that maybe it’s time we step up our flag game, city and neighborhoods both.
P.S. I didn’t get a Chicago flag tattoo. But I did look up “best flag tattoos” just to see what’s out there.
Explore all the Flags of Denver and learn the stories behind each design → View the collection
Thanks for following along and flying flags that tell stories. More soon.
– Steve