When it comes to popularity with tourists, New York City is the undisputed No. 1 in the U.S., drawing around 64 million visitors a year with its iconic pizzas, hot dogs, skyscrapers, museums, and boardwalk beaches.
There’s no doubt it has plenty to recommend it — but a trip there comes with a warning. It’s expensive and exhausting. The sidewalks are frantic, many attractions are miles apart, and you’ll pay a premium for a good hotel room.
Luckily, there’s an alternative that offers all of New York’s swagger but with far less stress — Chicago.
Here’s why you should ditch New York City and visit this Midwestern metropolis instead, from its legendary cuisine to public transport that’s an attraction in its own right.
1. Chicago is the birthplace of the skyscraper
New York City is tall, but Chicago gave birth to the skyscraper – the 138-foot Home Insurance Building, completed in 1885, is widely regarded as launching the high-rise era. There are thrilling observation decks incorporated across Chicago’s epic skyline, home to over 100 skyscrapers.
One is the dizzying 1,451-foot Willis Tower (formerly Sears Tower), the city’s tallest building. Here, visitors can enjoy views that stretch for up to 50 miles (on a clear day) from the Skydeck on the 103rd floor (1,353-foot up). And for a test of nerves, there’s The Ledge — where you stand in a glass box that extends 4.3-foot out over the street below.
A similarly hair-raising experience can be had at the 1,128-foot 875 North Michigan Avenue (John Hancock Center). The 94th-floor observation deck there features Tilt, which leans you out over the sidewalk at a 30-degree angle.
The building also has a restaurant in the clouds — the Signature Room.
What’s more, you can discover the city’s skyscrapers top to bottom. After taking in cloud-scraping panoramas, take the Architecture River Cruise, a fascinating narrated tour of Chicago’s iconic buildings from the water, a venture New York City simply can’t replicate.
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2. The pristine lakefront and urban beaches
From Manhattan, you need to travel for at least 45 minutes on the subway to reach a beach. In Chicago, the sandy shoreline is mere steps away from downtown — and it stretches for 26 miles along shimmering Lake Michigan.
In total, the Chicago Park District maintains 24 public beaches, featuring regular lifeguard patrols and a variety of activities to enjoy, including volleyball and DJ sets. There’s a pathway for walkers and cyclists — the 18-mile Lakefront Trail — that connects each strip of sand, meaning you can beach-hop seamlessly and enjoy jaw-dropping views of that immense skyline while you’re at it.
In New York City, the beaches are disconnected and there are no opportunities to sunbathe or swim under a glorious skyscraper.
Lastly, the fact that the beaches in Chicago are by a freshwater lake is another bonus. There’s no salt water to sting your eyes and corrode your gear, and no jellyfish to worry about.
Where to stay 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 exhausting for culture vultures. Yes, there’s “Museum Mile” along Fifth Avenue, home to The Met and Guggenheim, but some of the Big Apple’s best museums are up to six miles apart (American Museum of Natural History on the Upper West Side to 9/11 Memorial & Museum in Downtown, for example).
Chicago has a convenient cluster of world-class institutions minutes apart, with lakefront views to boot.
Top of your list to tick off should be the Art Institute of Chicago. Founded in 1879, it’s one of America’s oldest museums, and with a collection comprising over 300,000 pieces, it’s also one of the country’s largest.
Step between the bronze lions at the entrance, and inside you’ll find a world-class collection of impressionist paintings, including Monet’s Water Lilies and Vincent van Gogh’s The Bedroom, along with works by Andy Warhol, Pablo Picasso, Salvador Dali and Vasily Kandinsky.
Stroll 25 minutes south along Lake Michigan and you’ll discover the “Museum Campus.” Here, on a scenic peninsula, three world-renowned attractions sit side by side — the Field Museum, home to Sue, the most complete Tyrannosaurus rex ever discovered; the Adler Planetarium, where you can see stunning “Sky Shows” and study the heavens through a giant telescope; and the Shedd Aquarium, where more than 30,000 creatures are on display in over five million gallons of water.
Where to stay nearby
The Palmer House Hilton is just one block from the legendary Art Institute of Chicago.
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4. Better pizzas and hot dogs
New Yorkers are rightly proud of their pizzas, but Chicago’s deep-dish is on another level — literally. They’re akin to pies and practically a religious experience.
You’ll know you’re eating one of these belt-loosening creations if there’s a wall of buttery crust encasing layers of gooey cheese and a chunky crushed-tomato sauce. Sausage and vegetables often complete the mouth-watering picture.
The best places to try one? Lou Malnati’s, located at 439 N. Wells St., serves gold-standard pizzas; Giordano’s, at 223 W. Jackson Blvd in downtown, offers pizzas with a dough lid; and Pequod’s Pizza, at 2207 N. Clybourn Ave in Lincoln Park, offers delicious caramelized crusts.
The Chicago hot dog is equally sacred and assembled in a particular way.
If it’s authentic, you’ll notice an all-beef frankfurter — steamed or simmered — that has a satisfying snap when you bite into it.
The steamed poppy seed bun, meanwhile, will be soft and will never crack, and the ingredients will have been added in the following order — yellow mustard, bright green relish, chopped white onions, tomato wedges or slices, a dill pickle spear, sport peppers, and a dash of celery salt.
Ketchup, you’ll notice, is conspicuous by its absence. That’s because putting this sauce on a “Chicago dog” is a sin.
Top places to try one include Portillo’s (Downtown, 100 W. Ontario St.), The Wieners Circle in Lincoln Park (go after dark for the best staff banter), and vintage Superdawg Drive-In (6363 N. Milwaukee Ave.).
If fine dining is more your vibe, Chicago hits the same culinary heights as NYC. It’s home to two three-Michelin-starred restaurants, Alinea (Lincoln Park) and Smyth (West Loop), along with several others honored with one or two stars — from Oriole and Ever (both West Loop) to Kasama (West Town).
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5. The elevated train experience
New York City has a vast 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 discover the city’s top-tier delights, but it’s an attraction in its own right, passing so close to buildings that the line serves as an unofficial architecture tour.
Some of the spots where the train appears to brush against buildings include Harold Washington Library–State/Van Buren station (Red and Blue Lines), the Merchandise Mart (Brown and Purple Lines), and the Apple Store block on the Green Line.
Top attractions within a short walk of an L train station, meanwhile, include Cermak-Chinatown for Chinatown, Berwyn for the “shop local capital” of Clark Street, the California stop for buzzy Logan Square and Washington/Wabash station for a host of top sights, including Millennium Park, the Art Institute of Chicago, the Chicago Cultural Center, the Chicago Architecture Center, and the Chicago Riverwalk.
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6. It’s less crowded and the locals are friendlier
If you visit New York City, get ready to keep up — and don’t expect much help from the locals. The pace is frantically fast, the sidewalks are narrow and busy and New Yorkers have far too much on their minds to point you in the direction of your next bucket list attraction.
Chicago, by comparison, feels less hurried. You have space to get past people on the sidewalks without barging into shoulders — even in the most touristy areas — and the locals are more welcoming.
This is a major world city, but one with a relaxed, Midwestern heartbeat.
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7. It’s cheaper
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Both cities have world-class experiences — but you’ll pay less for them in Chicago.
Sometimes a lot less.
For starters, enjoying a luxury hotel room in central Chicago can often cost $200–$300 per night, compared to the $400 to $600 you’ll pay for something similar in New York City.
And for great sit-down meals — a deep-dish feast, for example — the bill will be around $25 to $40 per person versus $50 to $70 in NYC.
Chicago’s subway system is slightly easier on the bank balance, too, with the L train costing $2.50 to ride compared with $2.90 for the NYC subway.
Getting into the city from the airport is also better for budgets in Chicago, with the Blue Line from O’Hare Airport to downtown costing $5 versus $8.25 for New York’s JFK AirTrain.
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