Why Chicago Beats New York

Years ago, when I told a group of colleagues in New York that I was moving to Chicago, the reaction ranged from bemusement to outrage.

“Chicago?” one began, tentatively, as if they’d heard of the place but couldn’t quite place it. “Why would you want to live there?”

Another co-worker was more blunt.

“Chicago’s a dump,” he said. “You’ll be back in New York in a year.”

Like many New Yorkers who consider their city the capital of the world, he’d never actually been to Chicago, or anywhere else in “Fly Over Country.” My career ended up taking me away from Chicago after two stints totaling five years, but I never went back to New York, except for brief visits, and I never regretting moving to The Second City. How could I? I met the woman I would marry on my very first day in town.New Yorkers are always crowing that they live in the greatest city in the world. It is undoubtedly a singular place; perhaps the only can’t miss city in America for tourists alongside San Francisco. But I find all of the “We’re #1” bravado tiresome. There are a few things I like better in New York than Chicago – weather, weekend travel opportunities, pizza and bagels – but I’d much rather live in Chicago than New York for all of the following reasons.


Less Attitude

Chicago attracts young people from all over the Midwest, so although it’s a big city, there’s a friendly, middle-of-America vibe. New Yorkers tend to be friendly towards tourists but rather hard on each other. When I lived in New York, I found that native New Yorkers were often friendlier than transplants.

I have a couple friends who are Staten Island natives, and I’ll never forget how newly minted Manhattan residents from other parts of the country would mock them as “Bridge and Tunnel” people. For me, the locals with the accents who live in the Outer Boroughs are the real New Yorkers, not all the transplants who live in Manhattan and look down upon everyone else as soon as they get a 212 area code.

More Affordable

According to Bankrate.com’s cost of living comparison, New York Metro’s cost of living is about 95% higher than Chicago’s. In the Windy City, you can buy a fairly nice three-bedroom home in a nice, close-in suburb with good public schools for about $450,000; whereas that same amount of money barely buys a small condo in a sketchy neighborhood in New York.

In New York, I lived in a neighborhood called Bay Ridge, a long subway ride from Manhattan near the Verrazano Bridge in Brooklyn, because I couldn’t afford to live closer to my office in Manhattan. But when I moved to Chicago, I felt like there were only a couple of neighborhoods that were completely off limits due to price.

Chicago is also cheaper to visit. I was in town last week for a visit and got a room at the Hyatt at Michigan Avenue and Wacker for $55 on Priceline. No chance you’ll get a nice room in NYC for that price.

Lake Michigan

There are more bike paths in New York now than when I lived there but there’s still nothing quite like Chicago’s killer lakefront, which has an 18-mile-long bike path and several very nice sandy beaches, including one just steps away from downtown.

Better Smells

Thanks to the Bloomer Chocolate Company, the sweet smell of chocolate permeates the West Loop neighborhood but New York has more foul smells than good ones. If you Google “New York smells” or “What does New York smell like” the most common results involve urine.

You Can’t Get Lost in Chicago

If you give me the east/west coordinates of any address in the city of Chicago, I’ll immediately know where it is, thanks to the city’s street coordinates system. Midtown and Uptown Manhattan are straightforward but the rest of the city’s a mess and God help you if you need to find something in Queens.

Billy Crystal and Yoko Ono Have no Apparent Connections to Chicago

Chicago has a few obnoxious celebs, but New York has scores of them. Donald Trump. Rush Limbaugh. The Jersey Shore kids. (some of whom are from NY rather than NJ) The list goes on and on.

Vintage Street Signs

Chicago has more vintage street signs than any city in the country and these old beauties are emblematic of the way the city preserves its past, rather than bulldozing it.

The Green Mill and B.L.U.E.S. on Halsted

New York also has its share of small, atmospheric jazz and blues music venues, but there’s nowhere I’d rather hear live jazz and have a stiff cocktail than the century old Green Mill in Uptown, and if I could hear blues in just one place in the world, it would be B.L.U.E.S. on Halsted, which features authentic live bluesmen and women 365 nights per year.


It’s silly to claim that one city is definitively better or worse than any other city. One man’s paradise is another man’s prison. But for me, Chicago’s the most livable big city in the country. It’s a place where it’s easy to meet people, easy to fit in, no matter who you are, and hard to leave.

There are harsh, long winters that stretch into hot, humid summers, legendary traffic tie-ups, and miles of boredom outside the city limits in every direction. But there’s something about Chicago – the neighborhoods, the architecture, the people, the vibe – that has hooked me in a way New York never did. It’s a huge city that still manages to be a well-kept secret.

[Photos by Dave Seminara, TheeErin, Spiterman, Cliff 1066, Nimatardji Photography, mdanys and Michael Clesle on Flickr]