Explaining Chicago to New Yorkers is supremely gratifying

It’s a delight to watch the slow-dawning revelation that another American city might give NYC a run for its money.

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I'm often in the position of introducing Chicago to New Yorkers who've never before spent time here. Writer friends land on a book tour; old college pals pass through for family weddings; publishing colleagues come by on business. You can have a good sense of Manhattan even if you've never set foot there—the movies have seen to that—but Chicago isn't as familiar to the outsider. Watching ChiRaq, The Blues Brothers, and Perfect Strangers in quick succession won't do a thousandth of what Woody Allen accomplishes in an opening credits sequence. So they arrive, these hapless knickerbockers, expecting a few buildings and a baseball stadium and gangsters—historical and contemporary—in the middle of the corn, and they wind up fairly confused. While explaining Chicago to these people, it's a particular delight to watch the slow-dawning revelation that another American city might give New York a run for its money. And in describing our strange, beautiful town to them, I fully see it.

Without some help, New Yorkers will typically find their way only to the Loop and River North. They come away with the impression that Chicago is a sleek and festive city of museums, and yet conversely also a place full of lost, smiling, pasty people staring up at buildings. Imagining everything outside New York to be a small, flyover burg, they believe they've seen the whole thing. They wander two blocks west of a shopping district, find a sad Italian restaurant serving Mike Ditka-brand chardonnay, and assume they've found the finest dining the city has to offer.

When New Yorkers give their smug assessment of the city after five hours on the ground, how satisfying it is to inform them that they've been wandering in the midst of Nebraskans on vacation. That Chicago takes up ten times the area of Manhattan, and they've basically been exploring our Times Square. That they're judging things from the bottom of a tourist trap. That they, the chic and urbane, were the tourists. That they got trapped.

If the New Yorkers stay a bit longer, they begin to admire how clean Chicago is. At which point I hold forth about how Chicagoans store their garbage in alleys rather than in the middle of the sidewalk. "Kind of like how you might put your trash can in a kitchen cupboard, out of sight, rather than the middle of your living room." This is when I see the first glimmer of envy.

They've heard of Chicago dogs, and they're eager to try the same deep-dish pizza they can find anywhere these days. But I prefer to blow minds by introducing them to giardiniera, to the jibarito, to paczkis. Chicago's food is as good as New York's—if not better. And I don't even have to explain this part. The revelation is written on their faces midbite.

Do I take perverse delight in Chicago-splaining? Absolutely. I want New Yorkers to love us and leave us, to return home before I have to answer that inevitable question, "So where's your Brooklyn?" v

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