303+ Chicago Quotes To Inspire You In 2024 (Updated)

Today We put together a list of the best inspirational quotes for your chicago business, that are loved and highly shared throughout our Twitter, Instagram, and Facebook pages.

These chicago quotes are those little reminders we all need every now and then and some are powerful enough to inspire us for the whole week.

Here Are the 60 Most Inspiring Chicago Quotes

“Chicago is not just a city, it’s an attitude.” – Gary Johnson
“The pulse of Chicago is like that of a great heart, the heartbeat of a giant.” – Sara Paretsky
“Chicago has a strange metaphysical elegance of death about it.” – Claes Oldenburg
“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 is a city of contradictions, of private visions haphazardly overlaid and linked together.” – Pat Colander
“I have struck a city—a real city—and they call it Chicago… I urgently desire never to see it again. It is inhabited by savages.” – Rudyard Kipling
“Chicago is one city. We shall work as one people for our common good and our common goals.” – Harold Washington
“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.” – Stuart Dybek
“Chicago is the product of modern capitalism, and, like other great commercial centers, is unfit for human habitation.” – Eugene V. Debs
“Big shots are only little shots who keep shooting.” – Christopher Morley
“I adore Chicago. It is the pulse of America.” – Sarah Bernhardt
“This is Chicago, not the Soviet Union.” – Harold Washington
“I prefer a sane world where you are rewarded by providing people with something they want. Not arbitrarily rewarded in a status game that reminds me of chimpanzees.” – Charlie Munger
“If you’re going to be alive and on this planet, you have to, like, suck the marrow out of every day and get the most out of it.” – John C. Reilly
“Chicago is an October sort of city even in spring.” – Nelson Algren
“I don’t believe in failure. It is not failure if you enjoyed the process.” – Oprah Winfrey
“It is hopeless for the occasional visitor to try to keep up with Chicago. She outgrows his prophecies faster than he can make them.” – Mark Twain
“I’d rather be a lightning rod than a seismograph.” – Ken Kesey
“Chicago sounds rough to the maker of verse. One comfort we have: Cincinnati sounds worse.” – Oliver Wendell Holmes
“Sometimes you just have to put on lip gloss and pretend to be psyched.” – Mindy Kaling
“You can’t be that kid standing at the top of the waterslide, overthinking it. You have to go down the chute.” – Tina Fey
“Eventually, I think Chicago will be the most beautiful great city left in the world.” – Frank Lloyd Wright
“I’m from Chicago. My grandfather was a policeman, and my aunts are married to policemen.” – David Mamet
“Proud to have been born in Chicago, Illinois.” – Harpo Marx
“I prefer a straightforward, strong, communicative, not an anonymous, cowardly instrument of offense and defense.” – Robert Conrad
“In Chicago, you learn from the shadows.” – Mandy Patinkin
“All you need is a plan, a road map, and the courage to press on to your destination.” – Earl Nightingale
“So if anybody wants to get me something, get me 60 crabs – one for each year. I don’t want no diamonds, I don’t want no shoes, I don’t want no party. I want some crabs.” – Patti LaBelle
“The city of Chicago is a big part of everything I do.” – Mickey Cobras
“You can’t outwit fate by trying to stand on the sidelines and place little side bets about the outcome of life. Either you wade in and risk everything you have to play the game or you don’t play at all. And if you don’t play, you can’t win.” – Judith McNaught
“Chicago is not the most corrupt American city. It’s the most theatrically corrupt.” – Studs Terkel
“It’s hard to beat a person who never gives up.” – Babe Ruth
“Chicago is a city of neighborhoods.” – Mayor Richard M. Daley
“The city gives them love and in turn, they give love back to the city.” – Heather Eloise
“The city of Chicago and its people have given me so much.” – Michael Jordan
“Chicago is constantly auditioning for the world.” – Stuart Dybek
“Your time is limited, don’t waste it living someone else’s life.” – Steve Jobs
“Chicago will give you a chance. The sporting spirit is the spirit of Chicago.” – Lincoln Steffens
“It’s not the load that breaks you down; it’s the way you carry it.” – Lena Horne
“What I know for sure is that you feel real joy in direct proportion to how connected you are to living your truth.” – Oprah Winfrey
“Make sure your worst enemy doesn’t live between your own two ears.” – Laird Hamilton
“Chicago is the finest city on Earth.” – Russell Crowe
“The strength of a nation derives from the integrity of the home.” – Confucius
“Chicago will always be my roots.” – Common
“Do not wait for leaders; do it alone, person to person.” – Mother Teresa
“Chicago is a city that runs on adrenaline.” – Larry Potash
“I’ve always loved Chicago.” – Dwayne Johnson
“Be true to your work, your word, and your friend.” – Henry David Thoreau
“I adore Chicago.” – Sarah Bernhardt
“Do what you can, where you are, with what you have.” – Theodore Roosevelt
“Chicago is not the most corrupt American city. It’s the most theatrically corrupt.” – Studs Terkel
“Work hard, be kind, and amazing things will happen.” – Conan O’Brien
“Chicago is my favorite city.” – Michelle Obama
“Life is 10% what happens to you and 90% how you react to it.” – Charles R. Swindoll
“I’m from Chicago. My grandfather was a policeman, and my aunts are married to policemen.” – David Mamet
“The most difficult thing is the decision to act, the rest is merely tenacity.” – Amelia Earhart
“Eventually, I think Chicago will be the most beautiful great city left in the world.” – Frank Lloyd Wright
“The best way to predict the future is to create it.” – Peter Drucker
“Chicago will give you a chance. The sporting spirit is the spirit of Chicago.” – Lincoln Steffens
“Believe you can, and you’re halfway there.” – Theodore Roosevelt
“Chicago is constantly auditioning for the world.” – Stuart Dybek
“I never think of the future. It comes soon enough.” – Albert Einstein
“The city of Chicago is a big part of everything I do.” – Mickey Cobras
“Chicago is an October sort of city even in spring.” – Nelson Algren
“Don’t watch the clock; do what it does. Keep going.” – Sam Levenson
“The city of Chicago and its people have given me so much.” – Michael Jordan
“Success is not final, failure is not fatal: It is the courage to continue that counts.” – Winston Churchill
“Your time is limited, don’t waste it living someone else’s life.” – Steve Jobs
“Big shots are only little shots who keep shooting.” – Christopher Morley
“Chicago is not just a city, it’s an attitude.” – Gary Johnson

Top 50 Best Chicago Quotes

“Chicago is not just a city, it’s an attitude.” – Gary Johnson
“The pulse of Chicago is like that of a great heart, the heartbeat of a giant.” – Sara Paretsky
“Chicago has a strange metaphysical elegance of death about it.” – Claes Oldenburg
“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 is a city of contradictions, of private visions haphazardly overlaid and linked together.” – Pat Colander
“Chicago is the product of modern capitalism, and, like other great commercial centers, is unfit for human habitation.” – Eugene V. Debs
“Chicago is one city. We shall work as one people for our common good and our common goals.” – Harold Washington
“Chicago is an October sort of city even in spring.” – Nelson Algren
“I prefer a sane world where you are rewarded by providing people with something they want. Not arbitrarily rewarded in a status game that reminds me of chimpanzees.” – Charlie Munger
“I prefer a straightforward, strong, communicative, not an anonymous, cowardly instrument of offense and defense.” – Robert Conrad
“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.” – Stuart Dybek
“It is hopeless for the occasional visitor to try to keep up with Chicago. She outgrows his prophecies faster than he can make them.” – Mark Twain
“Chicago is a city of neighborhoods.” – Mayor Richard M. Daley
“I’d rather be a lightning rod than a seismograph.” – Ken Kesey
“Sometimes you just have to put on lip gloss and pretend to be psyched.” – Mindy Kaling
“You can’t be that kid standing at the top of the waterslide, overthinking it. You have to go down the chute.” – Tina Fey
“Chicago sounds rough to the maker of verse. One comfort we have: Cincinnati sounds worse.” – Oliver Wendell Holmes
“You can’t outwit fate by trying to stand on the sidelines and place little side bets about the outcome of life. Either you wade in and risk everything you have to play the game or you don’t play at all. And if you don’t play, you can’t win.” – Judith McNaught
“In Chicago, you learn from the shadows.” – Mandy Patinkin
“All you need is a plan, a road map, and the courage to press on to your destination.” – Earl Nightingale
“So if anybody wants to get me something, get me 60 crabs – one for each year. I don’t want no diamonds, I don’t want no shoes, I don’t want no party. I want some crabs.” – Patti LaBelle
“The city gives them love and in turn, they give love back to the city.” – Heather Eloise
“The city of Chicago and its people have given me so much.” – Michael Jordan
“Chicago is not the most corrupt American city. It’s the most theatrically corrupt.” – Studs Terkel
“It’s hard to beat a person who never gives up.” – Babe Ruth
“Chicago is a city that runs on adrenaline.” – Larry Potash
“I’ve always loved Chicago.” – Dwayne Johnson
“Chicago will always be my roots.” – Common
“The most difficult thing is the decision to act, the rest is merely tenacity.” – Amelia Earhart
“Chicago will give you a chance. The sporting spirit is the spirit of Chicago.” – Lincoln Steffens
“Believe you can, and you’re halfway there.” – Theodore Roosevelt
“I never think of the future. It comes soon enough.” – Albert Einstein
“The city of Chicago is a big part of everything I do.” – Mickey Cobras
“Chicago is constantly auditioning for the world.” – Stuart Dybek
“Your time is limited, don’t waste it living someone else’s life.” – Steve Jobs
“Don’t watch the clock; do what it does. Keep going.” – Sam Levenson
“Success is not final, failure is not fatal: It is the courage to continue that counts.” – Winston Churchill
“Big shots are only little shots who keep shooting.” – Christopher Morley
“Chicago is not just a city, it’s an attitude.” – Gary Johnson
“The strength of a nation derives from the integrity of the home.” – Confucius
“What I know for sure is that you feel real joy in direct proportion to how connected you are to living your truth.” – Oprah Winfrey
“Make sure your worst enemy doesn’t live between your own two ears.” – Laird Hamilton
“I adore Chicago.” – Sarah Bernhardt
“Chicago is my favorite city.” – Michelle Obama
“Be true to your work, your word, and your friend.” – Henry David Thoreau
“I never think of the future. It comes soon enough.” – Albert Einstein
“The city of Chicago and its people have given me so much.” – Michael Jordan
“Your time is limited, don’t waste it living someone else’s life.” – Steve Jobs
“Chicago is not the most corrupt American city. It’s the most theatrically corrupt.” – Studs Terkel
“Chicago is constantly auditioning for the world.” – Stuart Dybek

Short Chicago Quotes For Instagram

“Chicago, my kind of town.” – Frank Sinatra
“Windy City wonders.” – unknown
“Chicago blues, soul’s heart.” – unknown
“Concrete jungle, Chicago roars.” – unknown
“Chitown charm, irresistible allure.” – unknown
“City of big shoulders.” – Carl Sandburg
“Chicago, where dreams rise.” – unknown
“Lakefront beauty, Chicago’s pride.” – unknown
“City lights, Chicago nights.” – unknown
“Chicago skyline, dreams reach high.” – unknown
“Chicago, a symphony of neighborhoods.” – unknown
“City of deep-dish delight.” – unknown
“Chicago architecture, art in concrete.” – unknown
“Lake Michigan, Chicago’s embrace.” – unknown
“Charming streets, Chicago beats.” – unknown
“Chicago love, hearts united.” – unknown
“City of hope, Chicago cope.” – unknown
“Chicago, where blues talk.” – unknown
“Jazz melodies, Chicago’s heartbeat.” – unknown
“The Windy City blows me away.” – unknown
“Chicago roots, strong and deep.” – unknown
“City by the lake, Chicago awake.” – unknown
“Chicago, bold and vibrant.” – unknown
“City’s rhythm, Chicago’s hymn.” – unknown
“Chicago’s soul, stories unfold.” – unknown
“City of dreams, Chicago gleams.” – unknown
“Chicago, where art meets heart.” – unknown
“City of courage, Chicago’s heritage.” – unknown
“Chicago summers, memories in colors.” – unknown
“City lights, Chicago delights.” – unknown
“Chicago’s spirit, resilience we inherit.” – unknown
“City that works, Chicago’s perks.” – unknown
“Chicago’s pride, forever abide.” – unknown
“City’s embrace, Chicago’s grace.” – unknown
“Chicago’s soul, a story to behold.” – unknown
“City’s rhythm, life’s anthem.” – unknown
“Chicago’s heart, love never departs.” – unknown
“City’s pulse, diverse and multifold.” – unknown
“Chicago’s beat, our souls meet.” – unknown
“City of unity, Chicago community.” – unknown
“Chicago’s vibe, alive and thriving.” – unknown
“City’s culture, Chicago nurtures.” – unknown
“Chicago’s embrace, warm and safe.” – unknown
“City of dreams, Chicago’s schemes.” – unknown
“Chicago’s flavor, memories to savor.” – unknown
“City’s heartbeat, dreams complete.” – unknown
“Chicago, vibrant and alive.” – unknown
“City’s energy, Chicago synergy.” – unknown
“Chicago’s passion, a lasting impression.” – unknown
“City of stars, Chicago memoirs.” – unknown

Famous Chicago Quotes

“I’m from Chicago. My grandfather was a policeman, and my aunts are married to policemen.” – David Mamet
“Eventually, I think Chicago will be the most beautiful great city left in the world.” – Frank Lloyd Wright
“Chicago will give you a chance. The sporting spirit is the spirit of Chicago.” – Lincoln Steffens
“Chicago is not the most corrupt American city. It’s the most theatrically corrupt.” – Studs Terkel
“Chicago is constantly auditioning for the world.” – Stuart Dybek
“I prefer a sane world where you are rewarded by providing people with something they want. Not arbitrarily rewarded in a status game that reminds me of chimpanzees.” – Charlie Munger
“I prefer a straightforward, strong, communicative, not an anonymous, cowardly instrument of offense and defense.” – Robert Conrad
“It is hopeless for the occasional visitor to try to keep up with Chicago. She outgrows his prophecies faster than he can make them.” – Mark Twain
“Chicago is a city of neighborhoods.” – Mayor Richard M. Daley
“I’ve always loved Chicago.” – Dwayne Johnson
“Chicago is constantly auditioning for the world.” – Stuart Dybek
“Your time is limited, don’t waste it living someone else’s life.” – Steve Jobs
“The city of Chicago and its people have given me so much.” – Michael Jordan
“I never think of the future. It comes soon enough.” – Albert Einstein
“The city of Chicago is a big part of everything I do.” – Mickey Cobras
“Chicago is a city that runs on adrenaline.” – Larry Potash
“Chicago is my favorite city.” – Michelle Obama
“Be true to your work, your word, and your friend.” – Henry David Thoreau
“The city of Chicago and its people have given me so much.” – Michael Jordan
“Your time is limited, don’t waste it living someone else’s life.” – Steve Jobs
“Chicago is not the most corrupt American city. It’s the most theatrically corrupt.” – Studs Terkel
“Chicago is constantly auditioning for the world.” – Stuart Dybek
“Chicago will always be my roots.” – Common
“I’d rather be a lightning rod than a seismograph.” – Ken Kesey
“The city gives them love and in turn, they give love back to the city.” – Heather Eloise
“Chicago summers, memories in colors.” – unknown
“City lights, Chicago delights.” – unknown
“Chicago’s heart, love never departs.” – unknown
“City of unity, Chicago community.” – unknown
“City of dreams, Chicago’s schemes.” – unknown

Positive Quotes For Chicago

“Chicago, a city with a heart of gold.” – unknown
“In the heart of the Midwest, Chicago shines bright.” – unknown
“Chicago, where dreams take flight.” – unknown
“The Windy City blows in hope and possibilities.” – unknown
“Chicago, a tapestry of diverse cultures woven together.” – unknown
“In Chicago, every corner holds a story waiting to be told.” – unknown
“Chicago, a place where strangers become friends.” – unknown
“The spirit of Chicago never ceases to inspire.” – unknown
“Chicago, a city where resilience triumphs.” – unknown
“In Chicago, the skyline is not just buildings, but aspirations reaching high.” – unknown
“Chicago, a beacon of innovation and creativity.” – unknown
“In the heart of the city, you’ll find the heartbeat of Chicagoans.” – unknown
“Chicago, a city that embraces its past while forging a bright future.” – unknown
“The warmth of Chicago’s people makes the winters bearable.” – unknown
“Chicago, where every sunset paints the sky with vibrant hues.” – unknown
“In Chicago, community is not just a word, but a way of life.” – unknown
“Chicago, a city that dances to the rhythm of diversity.” – unknown
“The winds of change blow strong in Chicago, pushing us forward.” – unknown
“Chicago, a city that welcomes you with open arms.” – unknown
“In Chicago, hope springs eternal like the flowers in Grant Park.” – unknown
“Chicago, where the love for sports unites us all.” – unknown
“The beauty of Chicago lies not only in its architecture but in its people.” – unknown
“Chicago, a city where ambition meets opportunity.” – unknown
“In Chicago, each day brings a new chance to shine.” – unknown
“Chicago, where the sounds of jazz fill the streets with joy.” – unknown
“The heart of Chicago beats with a rhythm of unity.” – unknown
“In Chicago, the summer breeze carries the scent of adventure.” – unknown
“Chicago, a city that never stops moving forward.” – unknown
“The skyline of Chicago mirrors the heights of our dreams.” – unknown
“In Chicago, kindness is a currency that enriches us all.” – unknown
“Chicago, where the lakefront brings peace to the bustling city.” – unknown
“Chicago, a city that turns challenges into triumphs.” – unknown
“In the heart of Chicago, you’ll find a canvas of endless opportunities.” – unknown
“Chicago, a city that wears its scars with pride.” – unknown
“The pulse of Chicago is a reminder of the city’s vibrant energy.” – unknown
“In Chicago, hope is a flame that never extinguishes.” – unknown
“Chicago, a city that thrives on unity and diversity.” – unknown
“The streets of Chicago are paved with dreams and determination.” – unknown
“In Chicago, every neighborhood is a tapestry of stories waiting to be heard.” – unknown
“Chicago, where the joy of life is felt in every corner.” – unknown
“Chicago, a city that stands tall against the storms of life.” – unknown
“The people of Chicago are the heartbeat of this great city.” – unknown
“In Chicago, the possibilities are as vast as Lake Michigan.” – unknown
“Chicago, where art, culture, and creativity flourish.” – unknown
“Chicago, a city that fosters dreams and nurtures ambition.” – unknown
“In the heart of Chicago, you’ll find the soul of a city that never quits.” – unknown
“Chicago, where the future is as bright as the lights of the Magnificent Mile.” – unknown
“The spirit of Chicago shines like a beacon of hope.” – unknown
“In Chicago, unity is the glue that holds us together.” – unknown
“Chicago, where the pursuit of happiness is an everyday endeavor.” – unknown

Funny Chicago Quotes

“In Chicago, we put ketchup on hot dogs and call it a delicacy.” – unknown
“You know you’re from Chicago when you can pronounce ‘Wacker Drive’ correctly.” – unknown
“Chicago weather: Where you can experience all four seasons in one day.” – unknown
“Chicagoans: We’re experts at navigating potholes and construction zones.” – unknown
“In Chicago, deep-dish pizza is a food group all on its own.” – unknown
“Chicagoans can handle anything—except when the Cubs lose.” – unknown
“Chicago is the only place where ‘winter’ is a verb.” – unknown
“You know you’re in Chicago when you need to consult a map to find your way out of the parking garage.” – unknown
“Chicagoans are like pizza: a little cheesy, but everyone loves us.” – unknown
“In Chicago, parallel parking is an Olympic sport.” – unknown
“Chicagoans know that ‘rush hour’ is a daily battle for survival.” – unknown
“Chicagoans are so friendly, we’ll wave at you even if you cut us off in traffic.” – unknown
“In Chicago, we have two seasons: winter and construction.” – unknown
“You know you’re a true Chicagoan when you can tolerate sub-zero temperatures and complain about it.” – unknown
“Chicagoans: We’re masters of hibernation during winter.” – unknown
“In Chicago, ‘cold’ is a relative term. Anything above freezing is practically summer.” – unknown
“Chicagoans have a special talent for spotting tourists in Millennium Park.” – unknown
“You know you’re from Chicago when you can pronounce ‘Sauganash’ without hesitating.” – unknown
“Chicago is the only place where ‘dibs’ is a legitimate parking spot saver.” – unknown
“In Chicago, we have our own dictionary: ‘Da,’ ‘downtown,’ and ‘L’ are just a few examples.” – unknown
“Chicagoans don’t tan; we just go from pale to less pale.” – unknown
“You know you’re a Chicagoan when you complain about the humidity after surviving winter.” – unknown
“In Chicago, our sports teams give us a rollercoaster of emotions, and we keep coming back for more.” – unknown
“Chicagoans know that summer is just a break between winters.” – unknown
“You know you’re in Chicago when you can recognize the smell of roasted nuts on every street corner.” – unknown
“In Chicago, we call it ‘Lake Michigan,’ but it might as well be an ocean.” – unknown
“Chicagoans are experts at making small talk about the weather.” – unknown
“You know you’re from Chicago when you can’t imagine life without Portillo’s.” – unknown
“In Chicago, we don’t swim in the lake; we wade cautiously.” – unknown
“Chicagoans are so used to skyscrapers that we don’t even look up anymore.” – unknown
“You know you’re a true Chicagoan when you’ve lost a glove in the snow and found it in the spring.” – unknown
“In Chicago, we have summer festivals for every type of food imaginable.” – unknown
“Chicagoans: We don’t need beaches; we have the lakefront.” – unknown
“You know you’re in Chicago when you can navigate the ‘L’ system like a pro.” – unknown
“In Chicago, ‘spring break’ means you survived winter.” – unknown
“Chicagoans know that deep down, we’re all just Cubs fans waiting for our moment.” – unknown
“You know you’re a true Chicagoan when you can eat Italian beef without getting it all over yourself.” – unknown
“In Chicago, we don’t tan; we rust.” – unknown
“Chicagoans: We’re the kings and queens of layering clothing.” – unknown
“You know you’re in Chicago when you’ve developed a taste for Giardiniera.” – unknown
“In Chicago, we have street festivals for everything, even winter itself.” – unknown
“Chicagoans are pros at dodging pigeons in the Loop.” – unknown
“You know you’re a true Chicagoan when you can pronounce ‘Goethe’ correctly.” – unknown
“In Chicago, we embrace our Midwestern accents with pride.” – unknown
“Chicagoans know that our pizza slices are a meal in themselves.” – unknown
“You know you’re in Chicago when you consider 40 degrees to be ‘shorts weather.'” – unknown
“In Chicago, we don’t fear the cold; we just layer up.” – unknown
“Chicagoans are the world champions of complaining about the weather.” – unknown
“You know you’re a true Chicagoan when you’ve learned to spot the difference between fireworks and gunshots.” – unknown
“In Chicago, we have more ways to say ‘traffic jam’ than Eskimos have words for snow.” – unknown

My Personal Favourite Chicago Quotes

“Chicago, the city that stole my heart.” – unknown
“In the embrace of Chicago’s skyline, I found my home.” – unknown
“Chicago, where every corner holds a memory dear to me.” – unknown
“The vibrant energy of Chicago fuels my soul.” – unknown
“In Chicago, I discovered the true meaning of community.” – unknown
“The magic of Chicago lies in its hidden gems and surprises.” – unknown
“Chicago, the city that never fails to amaze and inspire me.” – unknown
“In the midst of Chicago’s chaos, I found my peace.” – unknown
“The love I have for Chicago runs as deep as the river that flows through it.” – unknown
“In the heartbeat of Chicago, I found my rhythm.” – unknown

We hope you enjoyed these inspirational chicago quotes today and that they helped your day be a little bit better.

Which chicago quote from above is your favorite and why? Share it with us in the comments!