Chicago may be the Second City to New York’s Big Apple, but after living here for over four years, I’ve never gotten the sense that the people here feel we live in a truly second city. Nobody much feels like we live in the shadow of the Manhattan skyline. Nobody much grumbles about New York, or curses it, or crows about how much better the Windy City is than the Big Apple. Nobody really feels the need. The attitude of Chicago seems to be, “hey, New York’s great, but I love living here.”

Still, since no one asked, I thought I’d settle the score. As a Chicagoan who just got back from spending four days in NYC, I feel absolutely qualified to make this judgment.

So, here you go folks, the final, definitive verdict on New York City vs. Chicago. Are we all ready? All right…


Chicago’s skyline is prettier, but New York’s is bigger. Both cities have their fair share of architectural marvels and both have distinctive features (New York’s fire escapes, Chicago’s back alley wooden stairs). Still, New York has the Empire State Building, a building less than a century old that’s nearly as iconic and legendary as the Pyramids. Advantage: NYC


This is tricky. One of the one hand, Chicago has the worst weather of any major city on earth. Freezing winters, hot muggy summers, and spring and autumn seasons that little better than myths. On the other hand… um… Advantage: NYC


Average rent for a one bedroom apartment in a nice neighborhood in Chicago: $800/month. The same in New York?: $750,000/month. Advantage: Chicago

Obnoxiousness of Local Baseball Fans

New York and Chicago baseball are pretty similar. There are two teams. One is a nationally-beloved team with a legendary history whose fans are deeply obnoxious because they know nothing of baseball and are just trying to look cool by rooting for the popular team. And there’s a team virtually unknown outside of the city whose fans are deeply obnoxious because they’re drunk. Advantage: Every Other City in the United States Except Boston


Some days, Chicago smells like chocolate. On a muggy day, Manhattan smells like hot, wet garbage. Advantage: Chicago


The homeless in Chicago are far easier to stalk and cannibalize. Plus they keep better in winter. Advantage: Chicago

Use of Local Bridges in Superhero Movies

The Queensboro Bridge was featured in Spider-Man. The Chicago River bridges can be seen in Batman Begins and The Dark Knight. Advantage: Chicago

Places to Buy Questionable-Looking Sausage While Standing in a Gutter

Chicago has lots of street fairs in the summer, but no pushcarts or food trucks, so Advantage: NYC

Famous Monster Attacks

Chicago’s Field Museum was the setting of that movie The Relic. Don’t remember that? You’ve heard of King Kong, though, right? Yeah. Advantage: NYC

Colors of Taxis

They’re all just yellow in New York. In Chicago, they’re all sorts of different colors, like a big bag of Skittles laying on their horns and driving too fast. Advantage: Chicago

Number of Dive Bars Run by Weird Old Scottish Dudes I Have Accidentally Stumbled Into

New York: 1 vs. Chicago: 0. Advantage: NYC


The Windy City of Big Shoulders vs. the Big Apple That Never Sleeps Gotham. Advantage: NYC

Residence of Austin H. Gilkeson

But for four glorious days in May, Advantage: Chicago

Overall Advantage: I can’t be bothered to go back and count.

So, there you have it, folks. Now you know.



Add yours →

  1. there is a prevailing attitude in Chicago of general contentment. A “well, we might be the Second City in the eyes of the rest of the nation but that’s on y’all and we could give a fuck.”

    Whereas a great many people I have met who have moved to NYC have done so for the explicit purpose of living on the cutting edge. Being first matters to these people, so much so that they’ve ironically decided to live in the one place where they are guaranteed to have more competition for the title than anywhere else. As you might expect there is then a lot of people who need the reassuring thought that hey, they are at least better than the people of Chicago by default.

    As a relative once said to me, “Chicago is about 2 years behind NYC.” Which would still put it about 5 years ahead of most of the United States. And never mind that NYC is constantly unsure of itself. Is Tokyo a half year ahead? London a full year? Oh you poor dears.

    (also your baseball entry on this countdown was perfectly written. I’ve never read a more concise take on Chicago baseball, New York Baseball, annoying fans, with a kickass punchline to boot.

    Go Tribe.

  2. Yeah, Chicago as a whole is pretty happy with its place in the world.

    I think you’ve nailed the New York Transplant Syndrome, the disease that causes recent arrivals in NYC to feel very special and unique for living in a place where more people live than anywhere else in the country.

    That’s the big difference between New York and LA, I think. People go to LA to pursue their dreams. Living in New York is the dream.

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