Curious Chicago Nicknames (And Why We Love Them)

Chicago: Home of the Blues, “Da Bears”, and Mrs. O’Leary’s cow. People love a clever slogan, and Chicagoans are no exception. In no particular order, here are some of the most interesting nicknames (besides the Windy City and Chi-Town) that have been inspired by this unique city.

The Second City

What started as a noble tribute was eventually turned into an attempt at an insult – and turned right back into a compliment. It was said that the “Second City” of Chicago arose after the Great Chicago Fire of 1871, as the “first city” was largely destroyed. Someone put a different spin on it, saying that it was a great nickname because Chicago was always going to be second to New York City anyway. The nickname was so popular that, even though Los Angeles had surpassed Chicago in population, it now lives on in various forms, including the acclaimed improv theater group.

The Big Onion

It comes from the original Potawatomi word that they used to describe the land that would become Chicago. Checagou means “wild onion” – or “stinking onion”, or “striped skunk”, or “skunk cabbage”, depending on who you talk to. Those wild onions were native to the swampland near what is now known as the Chicago River. Some researchers believe that there is a similar word in Chicago’s history that means “strong” or “great”, also referring to the Chicago River. (Does that mean that Chicago’s name was really another term for “the big stink”?)

The City That Works

This nickname began as a slogan used by or about Mayor Richard J. Daley, who literally ran the city of Chicago from 1955 to 1976. Its origin was attributed to comments on how well the elder Mayor Daley handled Chicago’s municipal services. The slogan isn’t actually unique to Chicago any more. Other mayors wanted their cities to be considered efficient and hard-working, too, so the phrase has since been used by Portland (Oregon), Stamford (Connecticut), Ypsilanti (Michigan), Vitoria (Brazil), and Haifa (Israel), among others.

My Kind of Town / That Toddlin’ Town

“My Kind of Town” is from the song of the same name by James Van Heusen and Sammy Cahn, and was popularized by Frank Sinatra in the movie Robin and the Seven Hoods (1964). “That Toddlin’ Town” is a phrase from a song called “Chicago”, written by Fred Fisher and featured in two well-known movies: The Story of Vernon and Irene Castle (1939), with Fred Astaire, and The Joker is Wild (1957), with Frank Sinatra. These two Chicago nicknames are listed together just because any nickname promoted by Frank Sinatra HAS to be cool.

The Chill

It’s not another weather report. This latest nickname translates into simply CHicago, ILLinois. Pop culture loves slick abbreviations, so we now have J.Lo, K-Fed, the OP, the OC, op eds, detox, retox, fo sho, mos def, and the Chill as part of our vocabulary (LOL). Nobody really says “electronic mail” anymore – it’s all email. The Chill is all Chicago. It’s a great place to hang out, it’s chilly in the winter, and it’s fun to say…unless you were one of those who thought Chi-Town was a silly name.

Eric Devlin is the Owner and President of Premier Transportation, one of the leading limousine companies. Having been in business for over 10 years, he has served stars such as Trent Resner, Jay Leno, Don Henley, and Axel Rose. Offering high-end limousine services to and from airports, as well as rentals for all special occasions, Premier provides safe, convenient, courteous, and reliable limousines services in Chicago and surrounding areas. To learn more or inquire about our services, visit Premier Transportation.

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