Looking for beautiful quotes about Chicago? The Windy City is second to none when it comes to fabulous travel quotes. So whether you’re looking for travel inspiration or Chicago Instagram captions, here are my favorite Chicago quotes!
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The Best Chicago Quotes & Chicago Instagram Captions
Here are my favorite quotes about Chicago, including inspiration from, poems, literature, pop culture, and quotes by famous Chicago authors!
Beautiful Chicago Travel Quotes
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. –
Eventually, I think Chicago will be the most beautiful great city left in the world. -Frank Llyod Wright
But never, among all the cities I have wandered over the years, cities all over the earth, did I feel and smell and sense anything quite like the verb that is Chicago; and always, no matter how many years passed, I could hear and see and touch something inside me that only Chicago has… –
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. –
It was so easy to disappear, so easy to deny knowledge, so very easy in the smoke and din to mask that something dark had taken root. This was Chicago, on the eve of the greatest fair in history. –
She is a novelty; for she is never the Chicago you saw when you passed through the last time. -Mark Twain
Come and show me another city with lifted head singing so proud to be alive and coarse and strong and cunning…proud to be Hog Butcher, Tool Maker, Stacker of Wheat, Player with Railroads and Freight Handler to the Nation. –
Big cities can have big hearts. –
Chicago happened slowly, like a migraine. First, they were driving through the countryside, then, imperceptibly, the occasional town became a low suburban sprawl, and the sprawl became the city. –
What is Chicagoness? What is the city made of? Why is it different from any other city? What are the things that are here and only here and compose the here of here? He leaned back in his lawn chair and thought a bit and then he said, The prevalence of the lake. The way the lake is a sea and not a lake. The way the lake shoulders the city. The cutting of wind off the lake and the whirl of snow. –
Chicago divided your heart. Leaving you loving the joint for keeps. Yet knowing it never can love you. –
Chicago does not go to the world, the world comes to Chicago! –
I adore Chicago. It is the pulse of America. -Sarah Bernhardt
She knew there was a big Chicago far off, where all the trains ran. –
Funny Quotes about Chicago
It is wonderful to be here in the great state of Chicago. –
Chicago has so much excellent architecture that they feel obliged to tear some of it down now and then and erect terrible buildings just to help us all appreciate the good stuff. –
In Chicago not only your vote counts, but all kinds of other votes-kids, dead folks, and so on. -Dick Gregory
I had thought Chicago was inevitable, like diarrhea. –
What a place to put a city, right on the front line of absolute zero. No wonder a cow burned it down. –
Here is the difference between Dante, Milton, and me. They wrote about hell and never saw the place. I wrote about Chicago after looking the town over for years and years. –
Chicago is not the most corrupt American city. It’s the most theatrically corrupt. -Studs Terkel
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
Chicago has a strange metaphysical elegance of death about it. -Claes Oldenburg
Quotes about Chicagoans
Let me tell you something. I’m from Chicago. I don’t break. –
One of the problems with people in Chicago, she remembered, was that they were never lonely at the same time. –
To be a Cubs fan is both a birthright and a curse. –
We’d speak French like a bunch of high school kids from Chicago, but we’d at least speak French. –
Quotes about Chicago Weather
Chicago is an October sort of city even in spring. –
I must confess a shameful secret: I love Chicago best in the cold. –
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
Love Travel Quotes?
I’m a little obsessed with travel quotes. If you are too, check out this massive guide to 250 Inspirational Travel Quotes & Travel Instagram Captions, plus:
- 101 Quotes about France to Inspire Your Travels & Your France Instagram Captions
- 101 Italy Quotes & Dreamy Italy Instagram Captions
- 101 Gorgeous Quotes About California & Fabulous California Instagram Captions
- 50 Stunning Hawaii Quotes & Hawaii Instagram Caption Inspiration
- 50 Quotes About Paris Celebrating Its Triumphant Beauty
- 50 Gorgeous Quotes about Scotland & Scotland Instagram Caption Inspiration
- 30 Quotes about Iceland Celebrating Its Mysterious Beauty
5 Things to Pack for Your Trip to Chicago
The Lonely Planet Chicago guidebook. It can be kind of a pain to find the major guidebooks once you land, or you’ll find them overpriced. I always like to pick mine up ahead of time.
An Unlocked Cell Phone so that you can use a local sim card while here to help navigate public transportation and when you’re on the road. (For people without American cell phone plans).
Backup Charging Bank for your cell phone since you’ll be using it as a camera, GPS system, and general travel genie.
A Great Day Bag so you can carry what you need with you (like your camera, snacks, water, sunscreen, cash, etc). My current favorite is the Pacsafe Citysafe, which is especially great for Chicago because it has many anti-theft features designed to deter pickpockets. It also transitions to a night bag more easily and won’t embarrass you if you go to dinner directly after sightseeing all day.
More Illinois Travel Resources
Don’t Forget About Travel Insurance!
Before you leave for Chicago make sure you have a valid Travel Insurance Policy because accidents happen on the road. I pay for World Nomads, and I happily recommend them. It’s especially important to get travel insurance if you’ll be hanging enjoying time in the beautiful (but occasionally slippery) outdoors.
I have been a paying customer of World Nomads for travel insurance for three years, and I happily recommend them. If you get sick, injured, or have your stuff stolen, you’ll be happy to have the ability to pay for your medical bills or replace what’s stolen or broken.