Back in 2018, radio host Justin Kaufmann and I cooked up a game called the Chicago Accent Challenge. Each Monday, listeners would call into Kaufmann’s radio show and answer questions such as “Welcome to Portillo’s, may I take your order?” and “How do you get to maa’s house?” in their best Chicago accents. The winner each week advanced to an live “accent-off” held at the Chicago Theatre at the end of the year. The defending champion is Jim Collins, who, it should be no surprise to hear, is an Irish electrician from Beverly. 

Another question we asked our contestants: How do you pronounce the name of our fair city on the lake?

This is a matter of local controversy. Merriam-Webster endorses four pronunciations of Chicago. One is “chi-CAW-go.” Another is “chi-CAH-go,” with the long “a.” The third and fourth are “chi-CAH-ga” or “chi-CAW-ga,” with an “a” sound rather than “o” sound at the end of the word.

Most of our callers, born-and-bred Chicagoans of a certain age, said “chi-CAW-go.”

“It’s only chi-CAW-go,” asserted Pat from Edison Park. Rod Sellers, a retired schoolteacher and historian who grew up on the East Side in the 1950s and ’60s, agreed. The only proper way to say “Chicago,” Sellers believed, is “chi-CAW-go.”

“If you hear someone say chi-CAH-go, ask them where they’re from,” said Sellers, who runs the Southeast Side Historical Museum. “Chi-CAH-go sounds like more of a transplant.”

Pat and Rod aren’t the only ones who feel that way. The DJs on WFMT say “chi-CAW-go,” emphasizing what a linguist once described as “that dark vowel.”

So does the Daley family. You can hear Richard M. pronouncing it that way at 2:04 in this speech:

And here’s Bill Daley doing it while announcing his 2019 mayoral campaign, at 0:12:

That ought to settle the issue, since being more Chicago than the Daleys is like being more Catholic than the pope. But even the Old Man mixed it up sometimes.

At his infamous press conference during the 1968 Democratic National Convention — when he mistakenly uttered, “the policeman isn’t there to create disorder; the policeman is there to preserve disorder” — Mayor Richard J. Daley said “chi-CAW-ga,” with the “a” sound at the end. Hear it at 2:03 in this clip.

When Daley was less agitated, though, he said “chi-CAW-go.” He did it during an appearance on the game show What’s My Line? in 1956. (Panelist Dorothy Kilgallen, a Chicago native, guessed Daley’s identity.)

I have to report, though, that “chi-CAW-go” is becoming an anachronistic pronunciation. When Barack Obama came out onstage in Grant Park after winning the 2008 presidential election, he began his victory speech by shouting “Hello, Chi-CAH-go!”

Mayor Lori Lightfoot also says “Chi-CAH-go.” You can hear it at the beginning of her budget address, at 1:21.

Obama and Lightfoot are both transplants, so that’s to be expected. But young, native-born Chicagoans, such as Chance the Rapper, also say “chi-CAH-go.” The distinction is not merely geographic, it’s generational.

Why are Chicagoans changing the way we pronounce our city’s name? Almost everywhere, regional speech is giving way to national speech. Millennials are much less likely to speak with local accents than Baby Boomers.

People outside of Chicago have always called our city “chi-CAH-go.” In this CBS News profile of Mayor Lightfoot, all the network news jagoffs say “chi-CAH-go.” As in so many other areas of speech, Chicagoans are adapting to the national broadcast standard. This “How to Pronounce Chicago Like an American” video features a young woman saying “chi-CAH-go.” Merriam-Webster also lists the “chi-CAH-go” pronunciation first.

Personally, I say “chi-CAW-go,” and recommend that all Chicagoans do the same. It’s the authentic pronunciation — the one that’s only used here in Chicago. When you hear someone say “chi-CAW-go,” you know you’re talking to a real Chicawgoan.

But Rich, who lives at Pulaski and Elston, doesn’t care which pronunciation you use.

“Chi-cah-go, Chi-caw-go, po-tay-to, po-tah-to,” is his attitude, and he’s as Chicawgo as anyone.