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21 quotes about Chicago that fill us with immeasurable pride

These famous folks say it best, with heartfelt quotes about the greatest city on the planet

Written by
Time Out Chicago editors
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Our love for Chicago runs so deep that sometimes it feels impossible to sum up our feelings about the city in a sentence or two. After all, how do you distill the spirit of Chicago's best attractions, its most beloved restaurants and its residents' cheerful but scrappy disposition? It's no easy task. Lucky for us, plenty of famous folks (and longtime residents) have commented on Chicago's splendor—including Frank Lloyd Wright, Barack Obama and Gwendolyn Brooks.

Love these quotes about Chicago? You can also find them at Time Out Market Chicago, where they're emblazoned on plexiglass partitions attached to tables throughout the space to help diners with social distancing. See you there for dinner and a dose of city pride!

RECOMMENDED: Brush up on the rules of living in Chicago

1. "Eventually, I think Chicago will be the most beautiful great city left in the world." —Frank Lloyd Wright, architect and Oak Park resident

2. "Chicago's neighborhoods have always been the city’s greatest strength." —Jane Byrne, Chicago's first female mayor

3. "There seems to be a different Chicago around every street corner, behind every bar, and within every apartment, two-flat, cottage, or bungalow. City of immigrants or city of heartless plutocrats, say what you will, Chicago almost defies interpretation. In many ways, Chicago is like a snake that sheds its skin every thirty years or so and puts on a new coat to conform to a new reality." —Dominic A. Pacyga, "Chicago: A Biography" (2009)

4. "I am an organic Chicagoan. Living there has given me a multiplicity of characters to aspire for. I hope to live there the rest of my days." —Gwendolyn Brooks, lifelong Chicagoan and first Black author to win the Pulitzer Prize

5. "Let me tell you something. I'm from Chicago. I don't break." —Barack Obama 44th President of the United States and longtime Chicago resident

6. "It is hopeless for the occasional visitor to try to keep up with Chicago—she outgrows his prophecies faster than he can make them. She is always a novelty; for she is never the Chicago you saw when you passed through the last time." —Mark Twain, author and humorist

7. "Going to Chicago was like going out of the world." —Muddy Waters, blues musician and Chicago resident

8. "One of the hallmarks of Chicago is that we do so many things in an original manner. What other city has made a river flow backwards? What other city makes traffic flow backwards?" —Mike Royko, Pulitzer Prize-winning  journalist

9. "It's 106 miles to Chicago, we've got a full tank of gas, half a pack of cigarettes; it's dark and we're wearing sunglasses." —Elwood Blues, "The Blues Brothers" (1980)

10. "Chicago is constantly auditioning for the world, determined that one day, on the streets of Barcelona, in Berlin's cabarets, in the coffee shops of Istanbul, people will know and love us in our multidimensional glory, dream of us the way they dream of San Francisco and New York." —Mary Schmich, Pulitzer Prize-winning columnist

11. "Anywhere in the world you hear a Chicago bluesman play, it’s a Chicago sound born and bred."Ralph Metcalfe, Olympic athlete and politician

12. "My first day in Chicago, September 4, 1983. I set foot in this city, and just walking down the street, it was like roots, like the motherland. I knew I belonged here." —Oprah Winfrey, media mogul and former Chicagoan

13. "Chicago is not the most corrupt of cities. The state of New Jersey has a couple. Need we mention Nevada? Chicago, though, is the Big Daddy. Not more corrupt, just more theatrical, more colorful in its shadiness." —Studs Terkel, radio host and oral historian

14. "I'm impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work." —Michael Douglas, actor

15. "I warn you, Jedediah, you're not gonna like it in Chicago. The wind comes howling in off the lake and gosh only knows if they ever heard of lobster Newburg." —Orson Welles as Charles Foster Kane in "Citizen Kane" (1941)

16. "Chicago is an October sort of city even in spring." —Nelson Algren, author

17. "Chicago is a city where the practical and the inspirational exist in harmony; where visionaries who made no small plans rebuilt after a great fire and taught the world to reach new heights. It's a bustling metropolis with the warmth of a small town; where the world already comes together every day to live and work and reach for a dream—a dream that no matter who we are, where we come from; no matter what we look like or what hand life has dealt us; with hard work, and discipline, and dedication, we can make it if we try." —Barack Obama 44th President of the United States and longtime Chicago resident

18. "I give you Chicago. It is not London and Harvard. It is not Paris and buttermilk. It is American in every chitling and sparerib. It is alive from snout to tail." —H. L. Mencken, journalist and cultural critic

19. "I miss everything about Chicago, except January and February." —Gary Cole, actor and Steppenwolf Ensemble member

20. "Yet once you’ve come to be part of this particular patch, you’ll never love another. Like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real." —Nelson Algren, "Chicago: City on the Make" (1951)

21. "Chicago is a town, a city that doesn't ever have to measure itself against any other city. Other places have to measure themselves against it. It’s big, it’s outgoing, it’s tough, it’s opinionated, and everybody’s got a story." —Anthony Bourdain, celebrity chef and author 

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