30 Beautiful Chicago Quotes & Chicago Instagram Caption Inspiration

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Last Updated on: 6th August 2021, 02:58 pm

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!

Read Next: 250 Inspirational Travel Quotes & Travel Instagram Captions

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Quotes about Chicago and Chicago Instagram Captions

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. –Nelson Algren

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… –Brian Doyle


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

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. –Erik Larson 

She is a novelty; for she is never the Chicago you saw when you passed through the last time. -Mark Twain

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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. –Carl Sandburg

Big cities can have big hearts. –Mary Elise Monsell

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. –Neil Gaiman

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.Brian Doyle


Chicago divided your heart. Leaving you loving the joint for keeps. Yet knowing it never can love you. –Nelson Algren

Chicago does not go to the world, the world comes to Chicago! –Peter Orner

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. –Carl Sandburg

Funny Quotes about Chicago

It is wonderful to be here in the great state of Chicago. –Dan Quayle

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. –Audrey Niffenegger

In Chicago not only your vote counts, but all kinds of other votes-kids, dead folks, and so on. -Dick Gregory

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I had thought Chicago was inevitable, like diarrhea. –John Varley

What a place to put a city, right on the front line of absolute zero. No wonder a cow burned it down. –Mark Helprin

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. –Carl Sandburg 

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. –Barack Obama

One of the problems with people in Chicago, she remembered, was that they were never lonely at the same time. –Lorrie Moore


To be a Cubs fan is both a birthright and a curse. –Jason Diamond


We’d speak French like a bunch of high school kids from Chicago, but we’d at least speak French. –Michelle Obama


Quotes about Chicago Weather

Chicago is an October sort of city even in spring. –Nelson Algren


I must confess a shameful secret: I love Chicago best in the cold. –Erik Larson

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

Read Next: 25 Hilarious Chicago Puns & Inspiration for Chicago Instagram Captions

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:

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5 Things to Pack for Your Trip to Chicago

Canada - Toronto -Luggage

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 Camera since Chicago is super photogenic. I use a mix of my Nikon D810 and my  Samsung8 smartphone these days.


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


Headed to Illinois? Check out more Chicago Instagram caption ideas. Plus, don’t forget to set aside time to visit The Lost City of Cahokia at Cahokia Mounds State Historic!

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.

Pin these Chicago Quotes & Chicago Instagram Captions for Your Trip!

Quotes about Chicago and Chicago Instagram Captions
Quotes about Chicago and Chicago Instagram Captions

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