WOnce popular among tourists, New York City, with its iconic pizzas, hot dogs, skyscrapers, museums and walking beaches, attracts about 64 million visitors annually.
No doubt it has plenty to recommend – but the trip there comes with a caveat. It is expensive and exhausting. The sidewalks are insane, many attractions are miles apart, and you’ll pay a premium for a nice hotel room.
Fortunately, there’s an alternative that offers all the heart-wrenching New York but with far less stress—Chicago.
That’s why you should ditch New York City and visit this Midwestern metropolis instead, from its legendary cuisine to public transportation that’s an attraction in itself.
1. Chicago is the birthplace of the skyscraper
New York City is tall, but Chicago gave birth to the skyscraper—the 138-foot-tall Home Insurance Building, completed in 1885, is widely regarded as ushering in the high-rise era. There are exciting observation decks all over Chicago’s epic skyline, home to over 100 skyscrapers.
One of them is the 1,451-foot Willis Tower (formerly the Sears Tower), the tallest building in the city. Here, visitors can enjoy views that stretch up to 50 miles (on a clear day) from the Skydeck on the 103rd floor (1,353 feet up). And to test your nerves, there’s The Ledge – where you stand in a glass box that extends 4.3 feet below the street.
At 875 North Michigan Avenue at 1,128 feet (John Hancock Center) you can have a hair-raising experience. The 94th floor observation deck there has a Tilt that bends you over the sidewalk at a 30-degree angle. And you can test your courage with a cocktail in the building’s CloudBar on the same floor.
In addition, you can explore the skyscrapers of the city from top to bottom. After taking in the cloudscapes, take the Architectural River Cruise, a fascinating narrated tour of Chicago’s iconic buildings from the water, a city that New York simply can’t replicate.
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2. Beside the pristine lake and urban beaches
From Manhattan, it takes at least 45 minutes on the subway to get to the beach. In Chicago, the sandy shoreline is just steps from downtown—and stretches 26 miles along sparkling Lake Michigan.
In total, the Chicago Park District has 24 public beaches that include regular lifeguard patrols and a variety of activities, including volleyball and DJ sets. There’s a path for walkers and cyclists – the 18-mile Lakefront Trail – that connects each strip of sand, meaning you can seamlessly join the beach and enjoy the amazing views of that massive skyline while you’re at it.
In New York City, the beaches are cut off and there’s no chance to sunbathe or swim under a majestic skyscraper.
Finally, the fact that Chicago’s beaches are located on a freshwater lake is another bonus. There’s no salt water to sting your eyes and eat your gear, and there’s no jellyfish to worry about.
Accommodation nearby
The Westin Michigan Avenue Chicago is moments from Lake Michigan and Oak Street Beach.
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3. World class museums within walking distance
New York City is boring for culture vultures. Yes, there’s a “Museum Mile” along Fifth Avenue that’s home to The Met and the Guggenheim, but some of the Big Apple’s best museums are within six miles (eg the American Museum of Natural History on the Upper West Side to the 9/11 Memorial & Museum downtown).
Chicago has a convenient array of world-class institutions minutes away from each other, with lakeside views.
At the top of your list should be the Art Institute of Chicago. Founded in 1879, this museum is one of the oldest museums in America, and with a collection of more than 300,000 pieces, it is also one of the largest museums in the country.
Walk between the bronze taps at the entrance and inside you’ll see a collection of world-class Impressionist paintings, including Monet’s. Water lilies and Vincent Van Gogh BedroomAlong with works by Andy Warhol, Pablo Picasso, Salvador Dali and Wassily Kandinsky.
Walk 25 minutes south along Lake Michigan and you’ll discover the Museum Campus. Here, on a scenic peninsula, three world-famous attractions sit side by side – the Field Museum, Sue’s House, the most complete Tyrannosaurus Rex ever discovered. Adler Planetarium, where you can see stunning “sky shows” and study the heavens through a giant telescope. and the Shed Aquarium, which features more than 30,000 creatures in more than five million gallons of water.
Accommodation nearby
The Palmer House Hilton is just one block away from the legendary Art Institute of Chicago.
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4. Better pizza and hot dogs
New Yorkers are rightfully proud of their pizzas, but Chicago’s deep dish is on another level—literally. They look like cake and are practically a religious experience.
If a wall of buttery crust covers layers of cream cheese and a crushed tomato sauce, you’ll know you’re eating one of these belt-loosening products. Sausage and vegetables often complete this picture.
Best place to try? Located at 439 N. Wells St., Lou Malnati’s serves gold standard pizzas. Giordano’s, at 223 W. Jackson Blvd downtown, offers crusty crust pizzas. And Pequod Pizza at 2207 N. Clybourn St. in Lincoln Park offers delicious caramelized crusts.
The Chicago hot dog is just as sacred and is assembled in a special way.
If it’s authentic, you’ll notice an all-beef frankfurter—steamed or boiled—that has a satisfying kick when you bite into it.
Meanwhile, the steamed poppy seed bread will be soft and never crack, and the ingredients are added in the following order – yellow mustard, light green relish, chopped white onion, tomato wedges or slices, dill spears, sport peppers, and a pinch of celery salt.
You’ll notice that ketchup is conspicuous by its absence. That’s because putting this sauce on a “Chicago Dog” is a sin.
Top places to try are Portillo’s (downtown, 100 W. Ontario Ave.), The Wieners Circle in Lincoln Park (go after dark for the best staff jokes), and the old Superdawg Drive-In (6363 N. Milwaukee Ave.).
If fine dining is more your mood, Chicago reaches the same culinary heights as New York. It is home to two Michelin three-star restaurants, Alinea (Lincoln Park) and Smith (West Loop), and several others that have been honored with one or two stars – from Oriole and Ever (both West Loop) to Kasama (West City).
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5. High train experience
New York City has an extensive subway system, but it’s functional—you ride it to get from A to B.
Chicago’s elevated rail system—the L train—not only helps you explore the city’s top-notch delights, but it’s an attraction in its own right, passing by buildings that serve as an informal architectural tour.
Some of the places where the train appears to hit buildings include the Harold Washington-State Library/Van Buren Station (red and blue lines), Merchandise Market (brown and purple lines), and the Apple Store block on the Green Line.
Meanwhile, top attractions within a short walk of an L train stop include Cermak-Chinatown for Chinatown, Berwyn for the “local capital of shopping” on Clark Street, California Station for bustling Logan Square, and Washington/Wabash Station for an array of top sights, including Millennium Park, the Art Institute of Chicago, the Chicago Cultural Center, Chicago.
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6. It’s less crowded and the locals are friendlier
If you’re visiting New York City, be prepared to walk—and don’t expect much help from the locals. The pace is maddeningly fast, the sidewalks are narrow and crowded, and New Yorkers are too much on their minds to guide you to the next bucket-list attraction.
By comparison, Chicago is less rushed. You have room to pass people on the sidewalks without bumping into them – even in the most touristy areas – and the locals are more welcoming.
It’s a big city in the world, but one with a quiet, Midwestern heartbeat.
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7. It is cheaper
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Both cities have world-class experiences—but you’ll pay less for them in Chicago.
Sometimes much less
For starters, enjoying a luxury hotel room in downtown Chicago can often cost $200-$300 per night, compared to $400-$600 for something similar in New York City.
And for fine dining—a deep-dish feast, for example—the bill is $25 to $40 per person, versus $50 to $70 in New York.
Chicago’s subway system is also a little easier on the bank balance, with the L train costing $2.50 compared to $2.90 for the New York subway.
Getting into the city from the airport is also better for the budget in Chicago, with the Blue Line from O’Hare Airport to downtown running $5 versus $8.25 for New York’s JFK AirTrain.
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