50 Chicago Quotes Honoring The Windy City

Look no further if you are looking for awesome Chicago quotes about The Windy City! 

Chicago is a city on Lake Michigan in the State of Illinois. 

Chicago is the most populated city in Illinois and the third most populated city in the United States. 

You might also enjoy these quote articles from people born in Chicago:

Chicago is known for its beautiful skyline, bold architecture, and museums. 

Check out these astonishing facts about Chicago below:

  • The TV remote, car radio, and mail-order retailing were all created in Chicago. 
  • The atomic age began in Chicago when the first self-sustaining nuclear chain reaction occurred.
  • The Willis Tower (formerly the Sears Tower) was the world’s tallest building for 14 years. 

Who originally inhabited Chicago, and how did it get its name?

The state of Illinois was formerly an indigenous territory. 

Traditionally, this area was the homeland of various native groups and tribes. 

The city of Chicago is between several significant waterways, naturally attracting different people. 

Some of the original inhabitants of this land were the Hoocak, Nutachi, Jiwere, and Baxojie tribes. 

The word “Chicago” is a French pronunciation of the word “shikaakwa,” which comes from the Algonquin language and means striped skunk or onion. 

However, after the United States continued its expansion, the US took many of these areas from the native peoples. 

Who founded Chicago?

One of the least-known facts regarding United States history is the notion that a Black man found one of the largest cities in the country. 

Jean Baptiste Point du Sable was Chicago’s first permanent non-indigenous resident. 

Du Sable is recognized as the man who founded Chicago. 

He was the son of a French soldier and an enslaved woman from Haiti. 

Du Sable was a master trapper, businessman, and trader who arrived in Chicago in 1780. 

He married a woman from the Potawatomi tribe, and they built a farm together near the mouth of the Chicago River. 

Many people refer to Du Sable as the father of Chicago because of his efforts to develop the area, establish trade routes and build up businesses. 

Many national landmarks honor Du Sable in Chicago today. 

If you want to learn more about the city of Chicago, check out our awesome Chicago quotes below for more exciting content. 

Short Chicago quotes about The Windy City

These short quotes about Chicago get right to the point! 

1. “Chicago ain’t no sissy town.” — Michael Hinky Dink Kenna

2. “We’re Chicago; we can do anything, damn it.” — Elva Rupio

3. “But when I go to Chicago, I know I’m home.” — Hank Sauer

4. “Theater in Chicago will always be my first love.” — William Petersen

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5. “Going to Chicago was like going out of the world.” — Muddy Waters

6. “Chicago Cubs fans are ninety percent scar tissue.” — George F. Will

7. “It is wonderful to be here in the great state of Chicago.” Dan Quayle

8. “My uncle was the town drunk-and we lived in Chicago.” — George Gobel

9. “After three years in Chicago, I decided to call it a career.”  — Ted Lindsay

10. “Chicago seems a big city instead of merely a large place.” — A. J. Liebling

The best famous quotes about Chicago

Here are some quotes about Chicago from a variety of people. 

11. “Hell has been described as a pocket edition of Chicago.” — Ashley Montagu, The American Way Of Life

12. “Gigantic, willful, young, Chicago sitteth at the northwest gates.” — William Vaughn Moody 

13. “Chicago has a strange metaphysical elegance of death about it.” — Claes Oldenburg

14. “The people of Chicago are a proud people; and for good reason.” — Jane Byrne

15. “Chicago is unique. It is the only completely corrupt city in America.” — Charles Merriam

16. “Being Irish was a big thing for me, particularly growing up in Chicago.” — Lara Flynn Boyle

17. “Welcome to Chicago. This town stinks like a whorehouse at low tide.” — David Mamet

18. “I’d rather be a lamppost in Chicago than a millionaire in any other city.” — William A. Hulbert

19. “The joy of working with the Chicago Symphony was immeasurable.” — Georg Solti

20. “I cannot watch the city of Chicago be destroyed by petty politics and bad government.” — Harold Washington

The top Chicago culture quotes about the all-American city

People from all over the country visit Chicago to taste the city’s unique spirit. 

21. “Chicago is a great American city. Perhaps it is the last of the great American cities.” — Norman Mailer, Miami and the Siege of Chicago

22. “Chicago is not the most corrupt American city. It’s the most theatrically corrupt.” — Studs Terkel

23. “You’d never think of taking a cab if you had to walk a mile down Chicago’s Michigan Avenue.” — Helmut Jahn

24. “Anywhere in the world you hear a Chicago bluesman play, it’s a Chicago sound born and bred.” — Ralph Metcalfe

25. “Chicago divided your heart. Leaving you loving the joint for keeps. Yet knowing it never can love you.” — Nelson Algren, Chicago: City on the Make

26. “I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.” — Michael Douglas

27. “Chicago is one city. We shall work as one people for our common good and our common goals.” — Harold Washington

28. “I love Chicago; it is unique in the world. So much intellect, so many artistic voices—it has fantastic potential.” — Jerome Sans

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29. “It’s one of the greatest cities on the planet. My heart beats differently when I’m in Chicago. It slows down, and I feel more at ease.” — Jeremy Piven

30. “After that, I started going downtown and doing a lot of theater shows in Chicago. When you go downtown there, it’s like you’re in New York; it’s like going to Broadway.” — Kel Mitchell

Chicago quotes expressing various opinions on the city 

People from Chicago call it home and miss the charm of the big city when they travel. 

31. “Chicago will give you a chance. The sporting spirit is the spirit of Chicago.” — Lincoln Steffens, The Autobiography of Lincoln Steffens

32. “And then when I went to Chicago, that’s when I had these outer space experiences and went to the other planets.”  — Sun Ra

33. “I like to go to Marshall Field’s in Chicago just to see how many things there are in the world that I do not want.” — Mother Mary Madeleva, My First Seventy Years

34. “There was no need to inform us of the protocol involved. We were from Chicago and knew all about cement.” Groucho Marx

35. “Because Chicago was to radio what Hollywood was to films and Broadway was to the theatre: it was the hub of radio.” — Mel Torme

More opinions about Chicago

36. “Chicago was a town where nobody could forget how the money was made. It was picked up from floors still slippery with blood.” — Norman Mailer, Miami and the Siege of Chicago

37. “When you feel like tellin a feller to go to the devil, tell him to go to Chicago. It’ll answer every purpose, and is, perhaps, a little more expensive.” Mark Twain

38. “I warn you, Jedediah, you’re not going to 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, Citizen Kane

39. “The trouble with you Chicago people is that you think you are the best people down here, whereas you are merely the most numerous.” — Mark Twain, Pudd’nhead Wilson’s New Calendar

40. “We struck the home trail now, and in a few hours were in that astonishing Chicago–a city where they are always rubbing a lamp, and fetching up the genie, and contriving and achieving new impossibilities.” — Mark Twain, Life on the Mississippi

Chicago architecture quotes about the uniquely designed city

Celebrate Chicago’s reputation for its large, unique architecture, and style. 

41. “In some Chicago neighborhoods, looking for a parking space is not unlike panning for gold.” — Gary Washburn

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42. “Germany was the cause of Hitler as much as Chicago is responsible for the Chicago Tribune.” — Alexander Woollcott

43. “You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.” — Ralph Kiner

44. “Chicago is a sort of journalistic Yellowstone Park, offering haven to a last herd of fantastic bravos.” — Ben Hecht

45. “A Chicago alderman once confessed he needed physical exercise but didn’t like jogging because in that sport you couldn’t hit anyone.” — Andrew H. Malcolm

46. “Chicago, mistress of the lakes, controller of our inland trade. The freest city of our states. What wondrous strides thy fame has made!” — Charles Frederick White, To Chicago

47. “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.” Oprah Winfrey

48. “Maybe we can show government how to operate better as a result of better architecture. Eventually, I think Chicago will be the most beautiful great city left in the world.” Frank Lloyd Wright 

49. “It is hopeless for the occasional visitor to try to keep up with Chicago–she outgrows her prophecies faster than she can make them.” — Mark Twain, Life on the Mississippi

50. “In Chicago, we may not think the Picasso presiding over the Richard J. Daley Center plaza is art, but we know it’s a big Picasso and it’s the city’s Picasso, and when the Cubs made the playoffs, the sculpture wore a baseball cap just like everything else.” — Pat Colander

Why do they call Chicago The Windy City?

It is a common practice for American cities to get a nickname. 

New York is The Big Apple, New Orleans is The Big Easy, and Las Vegas is Sin City. 

Chicago is often affectionately called The Windy City. 

However, despite popular belief, Chicago is not the windiest city in the United States. 

Chicago is not even in the top ten windy cities in the country. 

One of the first times Chicago was called the windy city was when Charles A. Dana, a reporter from New York, claimed that the Chicago politicians were “full of hot air.” 

New York and Chicago competed to host the World’s Fair. 

Dana attempted to discredit Chicago for some unscrupulous acts the city’s politicians made. 

However, he also attempted to brand the city as too windy and cold to host the fair. 

Despite his best attempts, Chicago won, and the World’s Fair was hosted there. 

What is your favorite Chicago quote?

Please, be sure to let us know in the comments below. 

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