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Chicago vs. New York City

Each week, Yahoo Travel pits rival destinations against each other to determine once and for all which one is the best. Up this week are two US rivals: Chicago and New York City.

Chicago vs. New York City

The Case for Chicago

by Bill Fink

Chicago has long been called the “Second City,” with a smaller population than insufferably packed New York City. But Chicago is first where it matters: quality of life for residents and visitors alike. This may come as a shock to New Yorkers, but it is possible to live in a big city and still be friendly. Chicago welcomes tourists with free city guides. In New York, they’ll knock you down if you hold hands or stop to take a picture.

Chicago is a city of firsts: It built the first skyscraper in the world, precursor to its stunning lakefront skyline; it raised the first Ferris wheel, the inspiration for the current ride on Navy Pier; it chewed the first Juicy Fruit gum, bringing us the city’s iconic Wrigley Building (and Wrigley Field!). Chicago has world-class art, architecture, dining, shopping, music, sports, really everything that New York has, but without the excessive cost and attitude. 

Related: Cheat Sheet: Chicago


The descendant of the world’s first Ferris wheel: Navy Pier Ferris Wheel (Photo: Thinkstock)

New York City’s myopic, self-absorbed viewpoint is best seen in the famous New Yorker magazine cover created to compensate for its citizens’ miserable quality of life. Bad news for New Yorkers: Unless you’re a billionaire hedge-fund manager, you’re living in an unaffordable, closet-size apartment, scurrying to work on packed streets like rats in a maze. Bad news for visitors: New York is full of New Yorkers. New York City is basically the A-Rod of cities: overpriced, overhyped, in love with itself, hostile to others, eventually to be proved a sham. Chicago is your logical first choice.  

Population: About 2.7 million in the city of Chicago, 9.5 million in the greater metro area


Before she took over the world, Oprah Winfrey conquered Chicago. (Photo: Getty Images)

Famous Faces: Oprah built her empire here, Michael Jordan celebrated championships, natives Siskel and Ebert shared movie advice, locals John Belushi and Bill Murray shared a few laughs, and Hugh Hefner shared a few photos. Don Cornelius added some soul, Kanye West started his musical career here, and Barack Obama began his political one. This is where Cyrus McCormick introduced the mechanical reaper to transform farming, and Enrico Fermi split the atom to change the world. And infamous Chicago gangster Al Capone? Born in Brooklyn. Thanks, New York.


Chicago’s other famous Ferris (Photo: Everett Collection)

Famous Films:  “The Blues Brothers,” “Ferris Bueller’s Day Off,” “About Last Night,” “The Fugitive,” “Ordinary People,” “Risky Business,” “Hoop Dreams.” New York was the setting for “CHUD,” “American Psycho,” and “Taxi Driver”— which perfectly captures that city’s hostile “You talkin’ to me?!” attitude.   

Popular Way to Get Around Town: Taking the “El” elevated railway that’s sometimes a subway gets you most anywhere you need to go. Advantage over New York: You can actually use the train to get to the city from both airports.   

Related: Chicago: Three Days, Three Ways

The Weather: Neither city will win any awards for weather, but New York has all the heat and humidity of Chicago summers, the same bitter cold winter, plus hurricanes! Advantage, Chicago.


Chicago’s peerless skyline (Photo: Thinkstock)

Architecture: Chicago’s skyline along the lakefront is spectacular, anchored by a couple of the world’s tallest skyscrapers in the Willis (Sears) Tower and Hancock Center (whose observatory was ranked “best view in America”). The city is filled with striking buildings from the famed “Chicago School” of architecture, which created the skyscraper concept in the 1890s (when skyscrapers were only 12 stories tall). Louis Sullivan, Mies van der Rohe, and Frank Lloyd Wright worked their art in and around town. The best way to experience it all is via the fascinating Chicago Architecture Boat Tour on the Chicago River, a trip that turns even the most skeptical into architecture buffs.  


Giordano’s deep dish pizza: better than New York’s? (Photo: Courtesy of Giordano’s)

Food: The deep dish delicacy of Chicago Pizza is rightly famous worldwide, with hearty helpings to be had at local legends Lou Malnati’s My π and Giordano’s. New York pizza is great — if you need something to soak up your alcohol after a night of drinking at overpriced bars. For fine dining, Chicago is home to 25 Michelin-starred restaurants, including the three-starred Alinea, ranked as one the top 10 restaurants in the world. The city has every variety of ethnic food, cheap eats, pub grub, and as Carl Sandburg’s “Hog Butcher for the World,” Chicago is a place where you can always get some locally sourced meat.

Related: Pizza So Good It Will Make You Book a Plane Ticket

Hot Dogs: Chicago-style hot dogs heaped with mustard, peppers, relish, onion, tomato, celery salt, and a stylish pickle spear are almost reason enough to visit this town. In contrast, the most popular style of New York hot dog is the “dirty water” flotsam sold from steaming vats by street vendors, suitable only for the unappetizing spectacle of an eating contest. Even global meat-tube authority Anthony Bourdain has officially declared Chicago to have the best dogs


The Art Institute of Chicago (Photo: Hanako’s Life, in a Flash/Flickr)

Entertainment: Museums, we got ’em, from the famed Art Institute to the dinosaurs at the Field Museum, all the fun buttons to press at the Museum of Science & Industry, and the cosmic light shows at the Planetarium. For theater, the Second City comedy club is the first source of talent for allegedly New York-centric “Saturday Night Live,” producing John Belushi, Mike Myers, Bill Murray, Gilda Radner, John Candy, and Tina Fey. For music, Chicago is home of the blues, with over a dozen clubs showcasing top live talent. And for sports, we have a football team that actually plays in the city, along with six-time champion Chicago Bulls. For baseball, the success (and associated hatred) of the New York Yankees is more than negated by the trash fire that is the Mets and the Knicks. And then there are the Cubs — great stadium, fun neighborhood that you can actually enjoy before and after a game, and a more relaxed atmosphere (due to extremely rare occurrences of World Series stress). I think Chicago also has a baseball team on its South Side.


Millennium Park (Photo: Terry Evans/Facebook)

Free Stuff: Chicago’s motto is “Urbs in horto,” or “City in a garden,” and as such, has a wealth of free parks in which to frolic, with lakefront Lincoln Park home of every sport imaginable (including Chicago-style 16-inch softball) and the excellent and free Lincoln Park Zoo. In the shadow of the Hancock Building, North Avenue Beach is just one of the many free lakeside locations where you can cool off on a hot summer day.  Alternatively, in New York City, you can go for a swim in the toxic Hudson River or sit for hours in traffic to get to a beach. Enjoy further free fun in Chicago by window shopping along Michigan Avenue, wandering Millennium Park, or checking out Buckingham Fountain’s light show, or enjoy one of many free concerts in Grant Park. New to town? Take a free tour with Chicago Greeter.


Manhattan skyline

The Manhattan skyline (Photo: Thinkstock)

The Case For New York City

by Meena Thiruvengadam

New York may be more expensive to live in than Chicago, but that’s the beauty of vacationing here: you can love it without having to pay Manhattan rents to live in it.

New York is the one place in the world everybody wants to experience. It is the backdrop for the movies and TV shows you grew up watching, and it’s a place where you really can find anything you’re looking for. The city’s five boroughs are thought to be home to a combined 800 languages. Within New York City’s borders, you can find some of the world’s best museums, best theaters, some amazing live music ventures and any type of food you could imagine eating.

There’s always something going on in New York and never a quiet night. Oh, and Beyonce lives in Tribeca.

Related: Cheat Sheet New York 

Beyonce at a Knicks game

Beyonce at a Knicks game (Photo: Getty Images)

Population: 8.41 million, 19.9 million (metro area)

Famous Faces: Celebrity spotting could be a sport in New York. Between the special events, Broadway shows, and hundreds of celebrities that call New York home, there’s no telling who you might run into. Manhattan alone has enough room for Tom Cruise AND exes Nicole Kidman and Katie Holmes. Beyonce, Neil Patrick Harris, Mariska Hargitay, Chelsea Clinton, Sarah Jessica Parker and Matthew Broderick — you name it, who doesn’t live in Manhattan? Patrick Stewart, Keri Russell and Norah Jones are in Brooklyn. The list goes on.

Sarah Jessica Parker in the West Village

Sarah Jessica Parker, strolling with her son through the West Village (Photo: Getty Images)

Famous Films: Two words: King Kong. The character from the 1933 classic had a co-star that’s since gone on to star in any more more iconic films: New York City. Ever watch “Fame,” “The Godfather,” “Goodfellas,” “West Side Story,” “When Harry Met Sally,” “Big,” “Home Alone,” or “Scent of a Woman?” And it’s not just the movies, New York has also had starring roles in “Sex and the City,” “Law & Order,” “How I Met Your Mother,” “Felicity,” “I Love Lucy,” and the “Cosby Show.”

Related: It’s Been 30 Years Since Ghostbusters?! Take the Green Slime Walking Tour of NYC in Homage

Popular Way to Get Around Town: A lot of American cities have good public transportation systems, but the New York subway trumps them all. The subway never shuts down and can take you pretty much anywhere you’d want to go. Trains runs underground in Manhattan, but several above ground lines in Queens and Brooklyn offer great views and a glimpse at some of the city’s most interesting neighborhoods. The subway runs to Manhattan from JFK. Trains are available from Newark, and a bus/train combination from LaGuardia can have you in to midtown Manhattan in under 45 minutes.

New York’s subway

New York’s subway (Photo: Thinkstock)

The Weather: New York and Chicago are somewhat similar when it comes to weather, but getting around New York in a blizzard is far more pleasant than wandering around Chicago in a blizzard. In New York, you can actually take a selfie in the storm without freezing off a finger or being blown away by winds coming off the lake.

Architecture: Chicago may have a few architectural icons of its own, but New York has One World Trade Center, which just took the America’s tallest skyscraper title away from Chicago’s Willis Tower. New York is home to a large and varied collection of skyscrapers that includes Art Deco icons the Empire State Building and the Chrysler Building. Prepare to look up and be awed — a lot.

One World Trade Center

One World Trade Center (Photo: Thinkstock)

Food: Both Chicago and New York are foodie havens, but Chicago can’t beat New York when it comes to the sheer number of available dining options. Deep dish is also an acquired taste that many people have yet to acquire. Seven New York City restaurants hold the coveted three-star Michelin rating, and New York’s often the one setting the trends. The Cronut came first, and Chicago’s Wonut is still trying to catch up.

Related: WATCH: Beyond the Cronut – Tasting New York

Hot dogs: It seems a little un-American to ban ketchup from hot dogs, but that’s practically what Chicago does. Just watch the snickers you get ordering a hot dog with ketchup in any authentic Chicago hot dog shop. Meanwhile in New York, you can have your hot dog any way you want it.

Related: Ruth Reichl’s Perfect Snacking Tour of New York’s Lower East Side

Entertainment: There will never be a shortage of things to do in New York. And whatever there is to do in Chicago, there’s more of it in New York. New York is home to more than 100 museums. Broadway alone has 40 theaters. Yelp lists reviews of 2,338 live music venues. New York’s got baseball, football, basketball and beaches. Whatever it is you’re looking to do, you’ll find it in New York City.


On Museum Mile in New York (Photo: Thinkstock)

Free Stuff: New York may be expensive to live in, but there are lots of fun things to do that don’t cost a dime. All summer long, there are free movies in Manhattan, Brooklyn, and Queens. Many of the city’s museums offer free and pay-what-you-wish nights. Several of its greatest attractions — Central Park, Prospect Park, the Brooklyn Bridge, Grand Central Station — are free. You can even see the Statue of Liberty for free by taking a round-trip ride on the Staten Island Ferry. And don’t be surprised if you happen to stumble on a free concert by a big name. Those happen a lot. Good Morning America and the Today Show both have free summer concerts and T-Mobile held a Shakira concert in Bryant Park last year.

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