New York vs. Chicago: Rating the Charms of the Big Apple and the Windy City

Beth Kaiserman


Two cities. One a thriving metropolis of Midwestern opportunity, the other a concrete nexus of humanity searching for answers.


Chicago and New York City. Both bustling with young people full of hopes and dreams. Both attracting hoards of newcomers eager to drink craft beers in the “up-and-coming” neighborhoods on the outskirts of downtown. Both buzzing with sexy new restaurants whose chefs present edgy modern fare.


Both places offer life, liberty and the pursuit of happiness all within reach -- or just a short train or bus ride away. But each city boasts its own charms, and at least one reason why its born-and-bred citizens won’t call anywhere else home.



Almost immediately upon thinking of these cities, one envisions their bright lights staggered across magnificent skylines, with people bustling like ants below.


In New York, the world-famous Empire State Building is a large attraction of the city’s skyline. Visitors take the elevator to the 86th and 102nd floors for two distinctive views of the city down below.


The building houses offices and made some notable eco-friendly improvements this past summer. The building’s radiators have barriers behind them to keep heat in, saving $190,000 per year, according to a June 2011 Newsweek article. The cooling system was also rebuilt to enhance energy flow, and sensors were installed to limit light and air waste.


In Chicago, the Willis Tower (formerly the Sears Tower, renamed in 2009) lingers over the city like a night watchman. It was the tallest building in the world when it was built in 1973 and held that status for almost 25 years. Today, the building’s 1450 feet and 110 stories make it the tallest building in the United States. Tourists can climb to the 103rd floor, or take a 60-second ride to the observation deck.


One World Trade Center in New York City is expected to surpass the Willis Tower in structural and crown height.


Both cities certainly love their sports. Both have baseball teams that are sewn tightly into the town’s fabric.


Chicago has the Cubs in the National League and the White Sox in the American League. The Cubs play at Wrigley Field, and though they have not won the World Series in 103 years, the area draws high traffic for its local bars and tailgating in Wrigleyville, which has become a living destination for young professionals in the past few years.


Of course, in the Big Apple, the New York Yankees are a force to be reckoned with, as are the Mets. Most New Yorkers have their preference, and both stadiums see a high turnout for games. The Yankees have long been known as rivals of the Boston Red Sox. For some fans, Yankee Stadium in the Bronx may never match The House that Ruth Built, nicknamed for Babe Ruth’s famous arrival from the Red Sox in 1919.


Like the buildings that define these cities’ landscapes, basketball also towers over the towns, with some notable history and a promising future. There’s the Chicago Bulls, where superstar slam-dunker Michael Jordan emerged (the team has been having a great season this year). Jeremy Lin has been making a splash for the New York Knicks recently, along with a very talented team of expert athletes.


Anyone not living under a rock in New York City felt a thump when the Giants pounded the Super Bowl this year over the New England Patriots, with Eli Manning as MVP. The New York Jets have a loyal fan base as well, and have taken on five playoffs in the 2000s. They share MetLife Stadium with the Giants. The Chicago Bears had their 700th win in November 2010, and hold the record for most overall wins over any other NFL franchise.


Of course, both cities are famous for pizza and hot dogs. Chicago has its signature deep-dish pizza, while New Yorkers have their thin crispy-bottomed slices. New York has the original Nathan’s hot dogs (and hot dog eating contest) on Coney Island, as well as street vendors offering simple all-beef wieners on-the-go. Gray’s Papaya and Katz’s Deli are also go-to spots for dogs. Chicago-style hot dogs offer a more complex experience, with various toppings that create more of a sandwich.


Chefs flock to Chicago and New York for expert culinary training and experience. From fine dining to food trucks to hole-in-the-wall haunts, both towns are filled with endless eating options. Foodies will advise to you to come hungry and don’t limit yourself.


Parks and Recreation

Aside from baseball, summer days can find New Yorkers and Chicagoans enjoying similar activities. Both towns have popular parks that are perfect for warm weather. Chicago has the lake, and New York has beaches at Coney Island and Rockaway. Both cities offer a wide array of free concerts and other activities in the summer months.


There’s no business like show business, and Broadway attracts tourists from far and wide to New York. Chicago is also renowned for its theater scene, as well as its wealth of comedy and famous comedians. Many “Saturday Night Live” stars started their careers at Chicago’s Second City, which celebrated 50 years in 2011.

New Yorkers vs. Chicagoans

“You talkin’ to me?” Though New Yorkers are often stereotyped as mean-spirited, that isn’t always the case. The truth is that when there are so many millions of people congested into one place, New Yorkers have to help each other. Anything to get the day moving faster: holding a subway door, giving directions, giving up a subway or bus seat for an elder or mother-to-be; these are not uncommon experiences in the city. As Joan Acocella points out in a 2008 Smithsonian article, New Yorkers really treat each other like they know each other.


As for Chicago, the kindness is perhaps more obvious. That Midwestern charm isn’t just a myth; one can feel right at home in the heart of the Windy City. It’s a more outward form of friendliness than the New York version (which at times may appear rather pushy).


Each glimmering metropolis has a wide variety of charms to explore, whether you’re downtown for a night out or venturing into one of the “up-and-coming” neighborhoods. Chicago and New York City are like jam  and preserves -- very similar, slightly different, and both equally sweet.


Author Bio:

Beth Kaiserman is a writer living in Brooklyn. Her interests range from food to theatre to dance, and include food while dancing. She is a contributing writer at Highbrow Magazine.


Photos of New York: ArtBron, Flickr; Fotopedia.

Photos of Chicago: Trey Ratcliffe, Flickr

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ArtBron, Flickr
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