Chicago: How to Get the Coasts to Really Respect You

Stop reading here. If you feel coastal cities like NYC and LA don’t give Chicago the equal respect it deserves, and you want to change this, then stop reading this article immediately, and simply let it go.

But you see, the fact that you won’t—the fact that you’ll keep reading hungrily on to the end to find the answer—reveals precisely the problem.

After a period of reorientation following my move here from NYC, I came to gradually embrace the unique things Chicago has to offer. Even though NYC is where I was born and raised, so that it remains closest to feeling like “home,” moving here has in unexpected, even beautiful, ways expanded my horizons of what a city is and can be. And I thank Chicago for that!

There’s only one thing creating an odd sort of energy between the city and me—this odd force field that being a coastal transplant, particularly a New Yorker, seems to activate here.

When I tell someone I’m from NYC, my experience thus far is that this provokes them to project something strange, almost otherworldly, onto me. I don’t know quite how to describe it. The way they begin to act is as if I were sent from some secret Gotham Committee to investigate Chicago, in order through my thorough research to confirm for the Committee for all time that NYC is indeed superior.

Even though this is an odd suspicion to have attributed to you, I try to put this in historical context and understand that in many ways locals might have reason for thinking this. There’s been a small but outspoken handful of douchey New Yorkers who, coming here, have tried to press the city under their thumb. Perhaps the most historic example is when, in 1952, A.J. Liebling, after a year here, returned to NYC to write the New Yorker article “Second City,” a moniker which this insightful WBEZ podcast shows Chicago quickly internalized as the intrinsic view of all New Yorkers.

When—that’s not the reality. In reality, coastals (at least this one, along with the vast majority of the others I personally know) really—I mean really—respect Chicago. But the perception prevails that I, as NYC transplant, am really here on a special assignment to judge the city. So, like clockwork, when I meet someone new in Chicago, it goes something like this:

“Where are you from?”

“I moved here from New York.”

The smile fades: “So which do you like more—NY or Chicago?”  

“Wow, I love both cities! I’d say there are aspects of both cities that I admire but also both cities have aspects I could do without.” This is always the wrong response, for my auditor interprets this to mean “Chicago sucks.”

To which imagined criticism they comeback: “Well Chicago is so much better than NYC!” (Pause here for just a second. I’ve experienced many variations at this pivot moment in the conversation. I once had a guy say, upon meeting him, “You realize you’ve left the worst city and come to the best city in the world, don’t you?” Another time, my Uber driver asked me where I was flying in from, and when I told him NYC, he said nothing more the entire trip; as at the end he dropped me off and handed me my bags, he said with a smile, “New York doesn’t have back alleys for their garbage the way our city does.” I relay another such story here.)

At this point, the Chicago local now launches into a one-way publicity campaign: “Chicago is so much better because of this, this, this, this….”

I’m never quite sure how to respond at such moments, even though they’ve occurred one too many times. Should I respond by simply being a good, humble guest and conceding their point? But talking trash about NYC feels like talking trash about my mama; as someone who lived 26 sublime years in NYC and for whom, if push comes to shove, it remains “home sweet home,” should I now get into it with them? Should I start listing things that are bad about Chicago and good about NYC? But now that wouldn’t exactly make me the good guest my mama taught me to be.

Other coastal transplants share the same story of moving here to be greeted with a similar deluge of projective defensiveness. Woody Sheraton narrates it this way:

Obviously we still had somewhat of a New Yorker’s accent when we came here. … So the question usually came up now and again about where we were from. “New York City” we’d reply. 99% of the time, we’d get the same question…”What was it like? Did you hate it?” When we’d say “no, we just needed a change in scenery” the persons who had posed the question would dig a little further. “So, do you like living here better than New York?” A loaded question. But one I had to answer honestly. “Not really, I like both cities. It was mainly the cost of living” was my standard reply.

This is where the conversation went in a strange direction…and this conversation always went the same way, no matter who the person was. It started to turn into a “my city is better than yours” type argument that neither my wife or I were looking for…or sometimes the people would not talk to us at all once they found out where we were from. Even though we were no longer living in New York, we’d often feel rejected, like strangers in our own city even several years after we’d lived here.

Wherefore this strange reactiveness? Across the past five years alone I’ve traveled to 15 global cities—from St. Petersburg, Russia, to Denver, to Buenos Aires, to Portland, to Helsinki—and I’ve not caught a whiff of anything like this.

May I pick at this Midwest scab for just a second?

The need to defend their hometown must not come from Chicago not being great—because of course it’s great.  New Yorkers will be the first to tell you! Sure, there will always be prigs like A.J. Leibling who turn their nose up at other cities—but such people are everywhere, including here (like those Chicagoans who like to bust on St. Louis or Phoenix).  But the reality is different when you interact with actual living, breathing humans from the coasts. Even my most rarefied and snobbish NYC friends love coming here, and when I’m back in NYC they speak about Chicago only in glowing terms: “Hey I read about that gorgeous new structure Jean Gang designed, and that spectacular new Grant Achatz restaurant that just opened—have you been yet?” What one finds is that a truly confident person is able to graciously praise the qualities of others. That respect, in the overwhelming majority of my experience, is in fact the coastal dialogue over Chicago.

But the problem, it seems to me, is that Chicagoans live in a perceived negative perception of themselves: the perception that the coasts live in a state of permanent disdain toward them. And it’s this that seems to breed the near-desperate responses I’ve encountered.  

Take, for instance, the fact that 25 restaurants in Chicago were awarded Michelin Stars this year. That’s mind-blowing! Enough said. Or is it? Across the Web and in conversation, I find Chicago eaters instead tortured by how many more stars New York got (triple that) and San Fran got (double that). Note in this Chicago Eater article how the writer actually asked the Michelin director what Chicago needs to do get as many stars as the latter two cities—as if somehow their achievements nullified Chicago’s. Another example among many, this one having to do with architecture: notice how this Chicago writer interprets the official designation of 1 World Trade Center as the tallest building in America to be a sinister effort on NYC’s part to, once again, best and humiliate Chicago—when the architecture council that decided this is in fact based in Chicago! As a result of this double-perception, as one former San Franciscan put it, “It feels like Chicago is always trying to prove itself in the pantheon of ‘important’ cities. Third Coast? Oy.”  

Because Chicagoans perceive the coasts as cruelly looking down on them, they lash back with an ingrained preemptive superiorityor what some would call “boosterism.”  

And that turns out to be a bit of an Achilles heel for Chicago, doesn’t it?

When NY transplant Rachel Shteir, in her infamous article “Chicago Manuals,” poked a fire brand into this vulnerability, Chicagoans went ballistic and deluged the New York Times with letters defending their city’s superiority. But they seemed to have missed Shteir’s point, which is not that “Chicago sucks”—for note that she elsewhere proves ready to point out things she likes here as well as NYC’s own flaws. Her point was that Chicago’s inferiority-turned-superiority-complex forms a bubble that keeps the city from being able to countenance realistically, let alone discuss soberly, its strengths together with its flaws.  

And finally, it makes the Windy City obsessin no way that’s reciprocated—over the perception of the coasts, particularly New York.

So if you’re a Chicagoan who’s read this far, my loving advice would be: Stop thinking about it. That’s it, let it go. (If you’ve begun to fume and want to troll me in the comments section below, remember: that proves you’re still caring far too much about what I think, when what I want is to set you free.) So stop thinking about what they’re all thinking about you, stop thinking about what you think they’re thinking about you, and just, awesomely, beautifully, be.

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Erick Sierra

Erick Sierra

Erick Sierra lives in Pilsen, Chicago. Visit his website at