In Chicago, the city flag is on everything, everyone

In Chicago, the city flag is on everything, everyone

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(Photo illustration by Elliott Ramos)

For Marines, it’s the eagle, globe and anchor.  For Michigan alumni, it’s maize and blue. For Chicago residents, it’s a flag bearing four red stars and two blue stripes.

Chicago’s municipal flag was adopted in 1917, but in recent years it’s made a leap from city buildings and police cars to pubs, storefronts, apartments, t-shirts, underwear, guitars, tattoos, soap—and even “American Idol” winners.

“It’s huge. People love Chicago and they love that flag,” said Jay Schwartz, a store manager for Strange Cargo in Chicago’s Lakeview neighborhood. 

He says that more people are manipulating and displaying the flag to identify with the city and make it their own. “It’s a super-easy thing that anybody’s who is from Chicago or anybody who knows Chicago recognizes instantaneously,” he said.

His store specializes in t-shirts and apparel, with many products bearing a Chicago theme, including shirts, hats and accessories that have the Chicago flag.

Chicagoans frequently try to best each other on matters of civic history, trivia, sports and politics.  They will fight over which hot dog is the best. They’ll keep track of political scandals like baseball stats. And they’ll scoff, angrily at times, if you say Willis Tower — the new “official” name for the storied Sears Tower. 

Behind the stripes and stars
Each of the white stripes stand for a particular Chicago area. The blue stripes stand for bodies of water, and each of the red stars stand for a significant Chicago event, with each of their six points having additional meanings.
North Side
Lake Michigan & North branch of the Chicago River

West Side

1st Star: Fort Dearborn

  • Points on the star:
  • Transportation
  • Labor
  • Commerce
  • Finance
  • Populousness
  • Salubrity

2nd Star: Chicago Fire

  • Religion
  • Education
  • Esthetics
  • Justice
  • Beneficence
  • Civic Pride

3rd Star: Columbia Exposition

  • France 1693
  • Great Britain 1763
  • Virginia 1778
  • Northwest Territory 1798
  • Indian Territory 1802
  • Illinois Statehood 1818

4th Star: Century of Progress

  • World’s third largest city
  • Urbs in Horto
  • “I Will” motto
  • Great Central Market
  • Wonder City
  • Convention City
Great Canal & South branch of the Chicago River
South Side

This competitive nature also fosters a deep civic pride. Residents, new and old, seeking to lay claim to the city and its neighborhoods like tribesmen, are sporting the city flag in ways outsiders would deem fanatical.

“I think more of the general public is buying the city of Chicago flag than used to be the case,” said Randy Smith, president of Advertising Flag Chicago. 

“If you asked people in the 1990s even, I’m talking Chicago people. [They] would have said ‘I thought that was the police flag,’ because the police wear it on the shoulder.” 

Smith’s company produces flags of all types, including the Chicago flag since 1936.  The company was started by his father who came to Chicago to sell items at the Century of Progress International Exposition, which was the World’s Fair held in Chicago from 1933 to 1934. This is not to be confused with the World’s Fair held in 1893, which was the subject of author Erik Larson’s best-selling book: The Devil in the White City.

Both events have left an indelible mark on both the city and its flag, taking the form of stars, which represent historic Chicago events.

Historic Design

The Chicago flag was created after Mayor William Hale Thompson appointed a flag commission in 1915.  A public competition garnered over a thousand entries, but the winner was a journalist, poet and lecturer named Wallace Rice.  And in classic Chicago fashion, Rice was also the same man the commission asked to write the rules for its flag competition.  Yes, even the flag was clouted. The City Council officially approved its adoption in 1917.

The flag’s four stars represent Fort Dearborn, the Great Chicago Fire, the Columbian Exposition and the Century of Progress. The blue stripes represent the Chicago River and the Great Canal, with the white stripes representing the city’s North, West and South neighborhoods. The original design started with just two stars, with the others being added in 1933 and 1939.

“People seem to be drawn to flags that have good design.  Chicago has one of the best flag designs for a city. That makes it easier to be popular in Chicago,” said Ted Kaye, author of the book Good Flag, Bad Flag.

 “There are five keys to a good flag design and Chicago follows all of them,” Kaye said. “It’s simple. It uses three colors. It has meaningful symbolism, doesn’t have lettering or seals and it’s distinctive.”

Kaye is treasurer for the North American Vexillological Association, vexillology being the scholarly study of flags.  His organization, founded in 1967, asked their members and the public to rank municipal flags in 2004.  Their rankings placed Chicago as the second best city flag, narrowly losing to Washington D.C., whose flag was based off the coat of arms of George Washington’s family.

Newcomers adopt flag as their own

Jack Nugent, owner of Ethically Engineered, is shown here making Chicago flag soap in his Edgewater residence. (WBEZ/Elliott Ramos)

It’s hard to pinpoint an exact time period in which the flag became a commodity, a praxis some would brandish as bona fide Chicago nativism.  There has been agreement amongst some observers that the impetus for the flag’s proliferation comes from the influx of younger professionals and college students who have flocked to the city since the early ‘90s.  Further, there have been instances of ex-Chicagoans wanting a way to identify their roots to outsiders, and doing so in the form of flag-laden apparel and tattoos.

Jack Nugent, a native from Urbana-Champaign, Ill., has noticed the uptick in the trend in recent years.

Nugent is the owner of Ethically Engineered, a business he runs from his apartment in Chicago’s Edgewater neighborhood. He sells what he calls vegan-engineered, no-impact products —the best-selling one being bars of soap made to look like the Chicago flag.

“It seems that the connection to the Chicago flag symbol is relatively new. I only created my product three years ago, but it seems like it’s been more than five years, but less than 10 years ago is when people started connecting to it.”

“[It became] where people weren’t seeing it just on municipal buildings and police cars, [they were] seeing it on t-shirts and messenger bags,” he said. “It’s relatively new, and I don’t find that native Chicagoans feel that connected to it.  I think that people [who] are most connected to the Chicago flag as a symbol are newer to the city and love those aspects of the city, but haven’t been here their whole life.  They are comparing life in Chicago to somewhere else –and they like it.”

Inking their pride

Lee DeWyze, winner of American Idol's ninth season, hails from the Chicago area and got a city flag tattoo during the final round of the competition with other contestants. (AP)

Nick Colella, a tattoo artist on the city’s North Side, agrees with Nugent’s assessment. A Chicago native, the 37-year-old has worked for 16 years at the Chicago Tattooing Company in the trendy Lakeview neighborhood. 

He has seen a noticeable uptick in tattoo requests for the Chicago flag or variations of it in the past 10 years. “It runs in waves.  I used to do three or four a month just of the flag alone. Sometimes you have people get the stars or just a star.”

 “[They] are usually younger and not from Chicago.  A lot of them are transplants, people who are from Schaumburg or those who afraid to say they’re from Palatine,” he said, referring to various suburbs.

His coworkers agreed, and made audible groans when asked about flag requests. “It seems that most people [who] get them aren’t from here, ” agreed Josh Howard, another tattoo artist at the shop. “It’s very popular with tourists,” chimed Dale Grande, another artist.

“Most people don’t even know what it means,” Colella said referring to the flag’s symbolism.  This happened so often that he created a chart for customers, which explains the meaning behind the flag’s stars, points and stripes.

Chicago expatriates show homesickness

One very noticeable display of the flag can be found on “American Idol” winner Lee DeWyze.  The 25-year-old musician won the ninth season of “American Idol,” and has been seen sporting his Chicago flag tattoo in media appearances and concerts ever since.

“My musical career started in Chicago. In the middle of being in L.A., I wanted to get something that represented where I’m from,” he said in an interview with WBEZ.

“I got it during the [Idol] contest. Some of the people don’t know what it means, but I like the history behind it,” he said after listing each of the star’s symbolic meanings.


DeWyze is from suburban Mount Prospect, but spent much of his early career living and working in Chicago.  He currently resides in Los Angeles, and is working on his second album.  He said “American Idol” producers had strongly suggested candidates avoid getting tattoos, as the bandages would not work well on television. “There were a couple of weeks where I was wearing long sleeves a lot,” he said.

DeWyze’s sentimental need to identify with his former home is shared by a fellow musician, Jon “Sully” Sullivan, who took his love of Chicago and manufactured a line of guitars themed with the city flag.

“When building the guitar and trying to decide on the color, the idea just hit me. While I’ve lived in the North Dallas area for nine years, I still consider Chicago to be home. To me, the skyline is prettier than any mountain I’ve seen.”

Sully builds his guitars out of his Texas workshop.

“The idea just hit me that I should put the flag on that guitar, and it’s definitely my “homesick” guitar. I’ve had a few people request the flag graphic on a couple of guitar orders. There’s just something about the flag; it’s a great design, and I always smile whenever I see it.”

Businesses and organizations, savvy to the behaviors of their newer consumers, have also found ways to surreptitiously insert the flag into advertisements, logos and announcements.  Groups ranging from softball leagues to bike enthusiasts have used some variation of the flag, such as swapping out the stars for red bike gears, baseballs or beer mugs.

“When it starts getting manipulated or parodied is when it gains traction,” said flag expert Ted Kaye.

Official Use

Despite the recent usage and display, the city flag still serves a municipal function.  It’s hung atop city buildings, airports terminals, courthouses, police departments, firehouses and ballparks.  During a much-publicized bid to win the 2016 Olympics, promotional material utilized stars from the flag, and it was openly suggested by many that a successful bid would have meant adding a fifth star to the flag.  Those hopes were dashed when the International Olympic Committee awarded the Olympics to Rio de Janeiro instead, which was a blow to former mayor Richard M. Daley.

When his wife Maggie died in November, Chicago flags around the city were lowered at half mast.

“Funeral homes will buy the Chicago flag for interment flags,” said flag producer Randy Smith.  Chicago ordinances allow for the display of the flag “upon line of duty death of an Illinois serviceperson.”  This includes draping the flag over the caskets of fallen police officers.

Chicago ordinances also outline rules for the description and presentation of the flag.  Interestingly enough, they also say it’s illegal to manipulate the flag:

It shall be unlawful for any person to use the municipal flag, standard, pennant, or badge, or any imitation or design thereof, except for the usual and customary purposes of decoration or display. No person shall print or stamp thereon or cause to be displayed thereon any letter, word, legend or device not herein provided for. Any person violating this section shall be fined not less than $5.00 nor more than $25.00 for each offense.

By the looks of it, many in Chicago have reason to hope this ordinance goes unenforced.

Email Elliott Ramos at

Correction & Amplification:
Ted Kaye is the treasuer of the North American Vexillological Association.  A previous version of this story incorrectly stated that Ted Kaye was the secretary of NAVA. 

Photos: Flag Fanatics

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