An Ode to Chicago: The City That’s Hard to Love

Chicago is a hard city to love. The windy city with subzero temperatures that rise and fall nearly 100 degrees in a few days causing whiplash to our skin and sanity. The city that barely shuts down or blinks an eye at feet of snow or sudden scorching temps with dense humidity. The city that loses people to greener pastures so often that makes it hard to get close to anyone for fear that they’ll leave.

But it’s also Chicago! The Chicago! City of Broad Shoulders and baseball and blues and hot dogs and comedy and brutal winters. It’s a city with its hard-working hands in almost every aspect of American culture, so why can’t others see what it so painfully obvious: Chicago is one of the best cities in America.

So why are people always leaving? Why can’t even Chicagoans see what I’ve always seen?

Downtown. Photo taken by me Nov. 14, 2016

I’ve wanted to live in Chicago since I was a little kid. I dreamed about it the way others dream of living in Paris or New York. My earliest memory is going to The Art Institute as a very small child, but my real love for Chicago all comes from a street on the far northside.

One summer Saturday my parents took my brother and I to Novelty Golf & Games in Lincolnwood. My mom grew up in the area after immigrating to Chicago from Cuba and this Saturday afternoon acted as a family-wide trip down her memory lane.

After playing mini golf, we drove from Lincoln and Devon toward the lake on Devon Avenue. On this relatively short drive that took us from far west to far east, I felt like we saw the world. We went from seeing Eastern European bakeries lining the street to heading into Little India where colorful saris replaced the traditional black suits worn by Orthodox Jews who were all gathering outside on benches. People sitting on benches on the sidewalk! That never happened in the spread-out suburb that we lived in. Our car filled with the smells of curry and cardamom until we got to La Unica, the Cuban grocery store, where the butchers remembered my mom from when she used to go there with her mother.

In a matter of minutes I had been surrounded by cultures that I rarely saw in my homogenous hometown 35 miles south of the city. That small drive made me fall madly in love with Chicago. It wasn’t the bean or the blues or a huge theatrical production. It was that street.

I went to college at North Park University, a northside school not far from that street with a huge population of Scandinavian students who taught me about fika and Finnish. Our small campus was surrounded by different cultures that couldn’t have been farther apart from one another from Lebanese and Arabic to Mexican and Sudanese. Instead of pizza and beer, we passed our time and hunger with hummus and mint tea. I was finally living in the global city I’ve always loved and it was everything I wanted, but after college I felt like I should leave Chicago. I felt like I should want to.

I went to New York where I heard the same refrain over and over: “New York is the greatest city in the world”. No matter what happened, New Yorkers were always confident their home was best.

I marveled at the confidence and was sometimes frustrated by it. When things went particularly bad in that global beacon where dreams are made of, I’d think to myself: how can this be the best city in the world? I knew one place that I felt was better.

I never fell in love with NYC the way I did with Chicago. I left New York which can feel like raising a white flag. That’s why there is a whole genre of essays devoted to people explaining why they left the city. It feels like a decision you have to explain more than quitting your job or eloping. You only leave New York in an acceptable manner to go to west to the other only-place-that-matters: Los Angeles.

Palmer Square Park, Chicago. Photo taken by me October 2017.

My move back to Chicago was supposed to be temporary. I was supposed to just do a one year masters program at Columbia College and take my higher degree with me to LA where I would hustle harder than ever before because if Los Angeles didn’t work out and New York didn’t work out, then I must not be cut out for the creative world. My second time in Chicago was supposed to be stopover home. The move west was the big plan.

But I didn’t do that.

It took me some time to admit it, but I love Chicago. I love it and I know it’s difficult to love. It’s like loving your petulant teenager. They can be a downright bitch to you some days, but the good days make it so worth. It makes you feel like you earned the love.

I love Chicago and I don’t hear that outpouring of love enough. Why don’t we all say that? Why don’t others feel that way? Why aren’t we saying things like “Chicago is the best city in the world” when we marvel at the glittering skyline which looks distinctly gorgeous from every side of the city. Why aren’t we saying “only in Chicago!” when we see a jazz quartet gleefully playing in the middle of Wicker Park’s four corners or when a celebrity like Chance the Rapper buys out a theater for people to see Get Out.

Yes, this city has problems. It has problems that need to be solved. It is segregated, but so is nearly every American city I’ve ever visited. There is gun violence, but now gun violence is everywhere. There are corrupt politicians, but Washington is currently a much more corrupt place.

I’d wager that our biggest problem as a city — one contributing to the others — is our low self-esteem. It’s hard to love someone who doesn’t love themselves.

I understand the lack of love — of trust — in this city, though. When your closest friends are more apt to leave for bigger industries in other cities or to settle down in the suburbs, you can feel left behind.

Our talented people migrate, leaving holes behind them to be filled. Their departures always hurt despite knowing that it happens and it will happen again like a very specific circle of life. We hate to see them go, but we buy into their notions that they have to. But do they have to? What if they stayed? What if they came back? Or what if they gave money made from their coastal adventures and success back to the communities they came from? What if they tried to nurture the soil that fed them?

Chicago needs to be loved so that it better gives back to us in the ways we need. A relationship is a two-way street and, sure, this is just a place. It isn’t a living, breathing human being, but places are special. A place can define, make and change us. A place can soothe the soul. A place is a home and homes are built best with love, even that love comes Chicago style and without ketchup.

Written by

Stephanie is a writer and comedian whose work has been featured on Reductress, Slate, The Weekly Humorist, The AV Club, Mental Floss, Atlas Obscura and more.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store