by Jill Halpin
✶ QUICK ANSWER: The Chicago flag has four red six-pointed stars representing Fort Dearborn (1803), the Great Chicago Fire (1871), the World’s Columbian Exposition (1893), and the Century of Progress Exposition (1933). The two blue stripes represent Lake Michigan and the branches of the Chicago River. The three white bands represent the North, West, and South sides of the city. Designed by Wallace Rice in 1917, it’s ranked the #2 city flag in America and is so beloved that there’s an entire website devoted to Chicago flag tattoos.
Why Chicagoans Are Obsessed With Their Flag
Here’s something you’ll notice about five minutes after arriving in Chicago: this city is obsessed with its flag.
It’s on front porches and fire stations. It’s on coffee mugs, guitar straps, shower curtains, and bars of soap. It’s woven into the jerseys of the Chicago Red Stars (the NWSL team literally named after the flag). Walk into any dive bar on the North Side or any tattoo shop on the South Side, and you’ll find at least one person with those four red stars permanently inked on their skin.
There’s an entire website — chicagoflagtattoos.com — devoted exclusively to photos and stories of people who’ve tattooed the Chicago flag on their bodies. Tattoo artist Amanda “Bats” Day at Tattoo Factory in Uptown says she could do a billion Chicago flag tattoos and never get tired of them. “The one thing they all have in common,” she told Block Club Chicago, “is they want to memorialize their love for Chicago.”
So what makes this particular city flag so special? Why does Chicago’s flag inspire the kind of devotion that other cities can only dream of? The answer starts in 1917, with a poet who covered his living room floor with hundreds of colorful rectangles.
The Origins of the Chicago Flag
In 1915, Chicago Mayor Carter Harrison Jr. decided it was time for Chicago to join the dozens of American cities that had adopted an official flag. The 1893 World’s Columbian Exposition had come and gone with nothing more than a red banner with a white Y-shape to represent the city — hardly the symbol a world-class metropolis deserved.
Harrison assembled a flag commission and turned to Wallace Rice — a Harvard-educated writer, poet, and lecturer on heraldry and flag history at the Art Institute of Chicago — to write the rules for an open design competition. The commission received over 1,000 entries.
And then something happened that could only happen in Chicago: the guy who wrote the rules also won the competition.
Rice had spent six weeks in his Lincoln Park home creating over 400 designs, spreading his favorites across his living room floor. He quizzed everyone who walked through his door — friends, delivery boys, even the milkman — asking which design they liked best. One was the overwhelming favorite: two horizontal blue stripes on a field of white, with two red six-pointed stars.
On April 4, 1917 — the same day the U.S. Senate voted to enter World War I — the Chicago City Council unanimously adopted Rice’s design. The vote was 63 Yeas, zero dissents.
What the Stripes and Bands Mean
Every element of the Chicago flag was chosen with deliberate intention. Rice described the white field as “the union of all the colors, to symbolize the union of all the races in the city of Chicago.” Here’s what each stripe represents:
The Three White Bands
The white areas of the flag represent the three geographic sides of Chicago. The top white band represents the North Side. The center white band — deliberately wider than the others — represents the West Side, reflecting its larger size. The bottom white band represents the South Side.
The Two Blue Stripes
The two light blue stripes represent the bodies of water that shaped Chicago’s development — and literally divided the city into its three sides. Rice described the color simply as “the color of water.”
The top blue stripe represents Lake Michigan and the North Branch of the Chicago River. The bottom blue stripe represents the South Branch of the Chicago River and the Chicago Sanitary and Ship Canal (the “Great Canal”), which connects the river to a tributary of the Mississippi River system — one of the most significant engineering feats in Chicago’s history.
The Four Stars: What They Mean
The stars are the soul of the Chicago flag — and they have a story to tell. Each one represents a defining moment in the city’s history. And here’s what makes them especially meaningful: the flag was designed to grow. Rice deliberately placed the original two stars off-center, closer to the staff, because he assumed the city would want to add more over time. He was right.
✶ First Star: Fort Dearborn (Added 1939)
The first star (closest to the flagpole) represents Fort Dearborn, a military outpost built in 1803 at the mouth of the Chicago River. This is where Chicago began — a frontier fort that grew into the trading post that grew into a city of nearly three million people. Its six points represent the political entities that have governed the Chicago area: France (1693), Great Britain (1763), Virginia (1778), the Northwest Territory (1789), Indiana Territory (1802), and Illinois (territory in 1809, state since 1818).
✶ Second Star: The Great Chicago Fire (Original, 1917)
The second star represents the Great Chicago Fire of 1871 — one of the original two stars on Rice’s design. The fire burned for two full days, destroying 17,000 buildings across more than three miles and leaving nearly 100,000 people homeless. Nobody knows exactly how it started (despite the Mrs. O’Leary’s cow legend), but we know it began in a barn on De Koven Street — where the Chicago Fire Academy stands today.
What makes this star so perfectly Chicago is what it really represents: not the destruction, but the rebuilding. The city’s “I Will” spirit was born in the ashes of 1871. Its six points stand for religion, education, aesthetics, justice, beneficence, and civic pride.
✶ Third Star: The World’s Columbian Exposition (Original, 1917)
The third star honors the World’s Columbian Exposition of 1893 — the other original star. This grand World’s Fair in Jackson Park celebrated the 400th anniversary of Columbus’s arrival in the Americas and announced to the world that Chicago was a major cultural and economic force. An astonishing number of things we use today were debuted at this fair: the Ferris wheel, the zipper, the Pledge of Allegiance, Cracker Jack, and the very concept of a midway.
Its six points represent the diverse governance of Illinois: France (1693), Great Britain (1763), Virginia (1778), the Northwest Territory (1798), Indiana Territory (1802), and Illinois statehood (1818).
✶ Fourth Star: Century of Progress Exposition (Added 1933)
The fourth star was added in 1933 for the Century of Progress Exposition (1933–34), a World’s Fair that celebrated Chicago’s centennial and showcased technological innovation during the depths of the Great Depression. Built on reclaimed land that is now Northerly Island, the fair embodied Chicago’s relentless forward momentum.
Its six points are pure Chicago bragging rights: the U.S.’s second-largest city (at the time), the Latin motto Urbs in Horto (“City in a Garden”), the “I Will” motto, the Great Central Marketplace, Wonder City, and Convention City.
💡 FUN FACT: The stars are six-pointed on purpose. When Mayor William Hale Thompson tried to change them to five-pointed “American” stars in 1928 (he hated anything that reminded him of Britain), Rice fought back fiercely: “I purposely made the stars six-pointed. Five-point stars are the symbols of states and could manifestly have no place in a municipal flag.” The City Council passed the change, but bizarrely, the ordinance was never recorded in the municipal code — and Rice’s six-pointed stars survived.
Why Six Points? The Story Behind the Stars’ Shape
This is one of those details that makes the Chicago flag so much more interesting than most people realize.
Wallace Rice was a heraldry expert, and he was very intentional about the star design. Five-pointed stars are traditional symbols of sovereign nations — think the American flag — and Rice felt they had no place on a city flag. He also wanted to avoid the Star of David, so he designed the points at a 30-degree angle instead of 60 degrees.
The result was something that had never appeared on any flag in the world before. Rice was proud of this — he called his creation “peculiarly and singularly a Chicago star, made by a Chicagoan for his greatly loved city, by an American in the tenth generation in this country.”
That kind of fierce, unapologetic civic pride? That’s Chicago in a sentence.
Will There Ever Be a Fifth Star?
Just like the American flag adds a star for each new state, Rice designed the Chicago flag to add stars as the city achieved new milestones. So the question has been debated for decades: what would deserve a fifth star?
Proposals have included Chicago’s role in the nuclear age (the first controlled nuclear chain reaction happened at the University of Chicago in 1942), the founding of the Special Olympics (which originated in Chicago), the Cubs winning the 2016 World Series (ending a 108-year drought), and Chicago’s response to the COVID-19 pandemic. Former Mayor Lori Lightfoot publicly floated the COVID idea.
The Chicago History Museum has an ongoing exhibition where visitors can vote on what a potential fifth star should represent. It’s one of those only-in-Chicago debates that people take seriously.
But after 85+ years with four stars, most Chicagoans feel the flag is perfect as it is. As one flag enthusiast put it: since it hasn’t changed in living memory for most people, the resistance to change is strong. The four-star flag is Chicago.
America’s Most Beloved City Flag
In 2004, the North American Vexillological Association (yes, there’s a professional organization devoted to flags) surveyed 150 American city flags. The Chicago flag scored an impressive 9.03 out of 10, placing it #2 behind only Washington, D.C. The association declared it “the standard by which all US city flags should be judged.”
But rankings don’t tell the full story. What makes the Chicago flag truly remarkable is how deeply it’s woven into the city’s culture. It’s not just a municipal symbol — it’s a statement of identity. Chicago Magazine noted that you’re almost as likely to spot the flag tattooed on a passing cyclist’s calf as you are to see it flying from a flagpole. The NWSL’s Chicago Red Stars are literally named after the flag’s stars. The MLS’s Chicago Fire references the second star’s meaning.
The flag appears on T-shirts, hats, messenger bags, guitars, golf balls, pillows, and even bars of soap. People reshape the stars into shamrocks for St. Patrick’s Day, hearts for Valentine’s Day, and pizza slices for… well, because Chicago. It’s distorted, remixed, and reimagined constantly — and somehow it always works, because the design is that strong.
💡 SPOT IT: Next time you’re walking around Chicago, try counting how many times you see the flag — on buildings, bridges, manhole covers, police cars, and fire trucks. The Chicago Architecture Center suggests this as a fun scavenger hunt, and trust us, you’ll lose count fast.
Where to See the Chicago Flag
The Chicago flag flies all over the city, but here are some of the most notable and photogenic spots:
Michigan Avenue Bridge — The flag flies prominently on the bridge over the Chicago River, one of the most photographed spots in the city.
City Hall (121 N. LaSalle St.) — Per city ordinance, the flag must be displayed on City Hall at all times.
Navy Pier — The flag is visible throughout the Pier, often photographed with the Centennial Wheel in the background.
Wrigley Field — Look for it flying on game days alongside the American flag and the famous “W” or “L” flag.
Chicago History Museum (1601 N. Clark St.) — See the flag up close, learn more about its history, and vote on whether there should be a fifth star.
Everywhere else — Front porches in Bridgeport, coffee shops in Logan Square, barbershops in Pilsen, breweries in West Loop. Chicagoans fly their flag the way Texans fly theirs — with zero irony and maximum pride.
In 1917, the publication Chicago Commerce predicted that Chicagoans “will always look upon the elements of their flag with pride and pleasure because in a way it is descriptive of their being and spirit.” More than a century later, that prediction hasn’t just come true — it’s an understatement. The Chicago flag isn’t just a flag. It’s a love letter to a city that burned to the ground and built itself back, that hosted the world and dazzled them, that keeps growing and fighting and reinventing itself while never forgetting where it came from.
Four stars. Two stripes. One city. ✶
More to Explore in Chicago
- First-Time Visitor’s Guide to Chicago
- Chicago Riverwalk Guide
- 21 Top Things to Do in Wicker Park
- 10 Best Things to Do With Kids in Lincoln Park
- Hidden Speakeasies in Chicago
- 20 Most Haunted Places in Chicago
- Complete Guide to the Chicago CTA
About the Author
Journalist Jill Halpin is a Chicago-based travel expert who spots the Chicago flag roughly 47 times on every walk through the city — and still gets a little thrill every single time.