Why New Yorkers Shouldn’t Look for Sweet Home in Chicago


A recent discussion thread in the popular, urbanist City-Data Forum asked readers for reasons why some people shouldn’t move to Chicago. That got me thinking about the time I encountered a pair of typical New Yorkers on my Marina City roofdeck. One of them was like me, a New Yorker who loves the rest of the world. The other was the kind of Gothamite the rest of the world loves to hate: a New Yorker who thinks everywhere else should be like New York.

Those are the New Yorkers who probably shouldn’t travel far beyond the safety of a 24-hour subway system. In answer to the question posed on City-Data, a good reason not to move to Chicago is if you’re a New Yorker like the above who can’t wrap your mind around the fact that every other major city on the planet doesn’t necessarily feel like the five boroughs.

Our skyline notwithstanding, compared to other popular, large U.S. cities (I’ll avoid just comparing us to the other Alpha cities, that would be too narrow a comparison), Chicago’s draw tends to be a bit esoteric. We’re the kind of city that it takes time to fully appreciate–and fall in love with. Not the least reasons for that being we tend to have a slower pace and a greater sense of modesty than other major U.S. cities.

A fair number of New Yorkers come to Chicago and most love the place. Some New Yorkers–like me, for instance–move here and decide to stay very happily forever. But some other New Yorkers visit here and spend hours complaining how Chicago is not New York. It’s annoying for Chicagoans and a great way to make no friends out of them.

Comparing and contrasting high-rise Chicago with high-rise New York is akin to sizing London up against Paris and complaining that one isn’t exactly like the other even though they’re both relatively low-rise world cities. It’s a category error my fellow New Yorkers make all the time–the assumption that only cities that feel as animated and crowded as New York can have huge high-rise skylines. That assumption may work for places like Hong Kong or Sao Paulo (not that we approach either of their populations in Chicago).

But the Windy City feels amazingly different than New York. Not just a little, but a hell of a lot different. Even with the Loop, 25 miles of lakefront skyscrapers, and a huge, old rapid-transit system, Chicago isn’t a little New York and never has been. Experiencing that coming-to-Jesus realization in person is probably the biggest reason some New Yorkers are so put out by Chicago. This city is confusing to them in ways they never expect.

It’s also probably not a good idea to move here if you’re afraid to wear longjohns, a hat, a scarf, and gloves. If I had a nickel for every visitor I’ve heard complain about our winters as they stood in the snow on State Street in a windbreaker, I’d be a rich blogger. I tell my New York friends when people move here and continue to dress like that, sometimes we just lead them to Lake Michigan and push them through the ice.

They actually think I’m kidding.

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