Making the tough choice of Chicago vs. New York City? We’ve put together a brief comparison of the two cities and their top attractions and activities. See which seems more enticing, from river cruises to street food. Learn how to save on admission to the best things to do in each city below.
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Observation decks
Both NYC and Chicago have two stellar observation decks from which to see the best sights of their respective cities. Many people choose to visit both observation decks. But it’s also easy to pick your favorite and see the aerial views from your chosen landmark. Here’s a brief comparison of the four observation decks.
New York
New York
- Empire State Building. Among the most iconic buildings in New York City, the Empire State Building offers an 86th-floor observation deck with panoramic views. It’s located in midtown Manhattan and boasts a refined Art Deco aesthetic.
- Top of the Rock. Located in the famous 30 Rock Building, Top of the Rock Observatory is famous for its unobstructed 360-degree views and convenient location in Rockefeller Plaza.
Deciding between these two? Check out our Top of the Rock vs. Empire State Building breakdown.
Chicago
Chicago
- 360 CHICAGO. Housed in 875 N. Michigan —itself containing several shops and restaurants— 360 CHICAGO is located on the 94th floor and provides unbeatable views of the waterfront. Many visitors also enjoy their upgradeable experience called TILT.
- Skydeck Chicago. Located in what used to be known as the Sears Tower, Skydeck Chicago provides stellar views from 1,353 feet up in the air on the 103rd floor. Visitors can see parts of four different states from this observation deck.
Art Museums
Chicago and NYC offer pretty stiff competition when it comes to museums. They both feature some of the best museums in the world. Additionally, many of the most-visited art museums are found in these two cities. Here’s a quick rundown of the biggest art museums in each city.
- Metropolitan Museum of Art. Among the best art museums in the world, the Met boasts massive collections of everything from Ancient Egyptian artifacts to medieval armor to eighteenth-century portraiture.
- Museum of Modern Art (MoMA). One of the finest and most extensive collections of modern art in the entire world, MoMA is home to many famous works of art by the biggest names in recent history—Warhol, Pollack, Van Gogh, Gaugin, and many more.
Check out our recommendations for must-see things at the Metropolitan Museum of Art.
Chicago
Chicago
- Art Institute of Chicago. Just as prestigious and often more frequently visited than the Met, the Art Institute’s collections also span much of human history and include everything from impressionist paintings to satirical prints.
- Museum of Contemporary Art. The MCA is much smaller than MoMA and focuses instead on truly contemporary works of art, including a great deal from living artists. A visit here is a good opportunity to see the art world as it is evolving today.
Natural History Museums
Each city boasts one impressive natural history museum. Both are renowned for their fine collections of natural objects and as well as their cutting-edge research. Here’s a brief look at what they each offer.
New York
New York
- One of the largest such institutions in the world, the American Museum of Natural History is well known for its collection of dinosaur fossils, gemstones, and an expansive collection of ocean life.
Chicago
Chicago
- The earliest collections at the Field Museum were donated from the Columbian Exposition in 1893, but they’ve expanded far beyond that scope to include millions of artifacts, objects, and even the most famous dinosaur skeleton in the world: SUE the T. Rex.
City Tours
City Tours
Chicago and New York City both have more to see than you can accomplish in one trip, or even two. That’s where a comprehensive tour can come in handy. These popular bus tours are the best way to see each city efficiently. Here are our picks for the top bus tours in each city.
New York
- Hop-on Hop-off Bus Tour. This hop-on hop-off option from Big Bus New York offers unlimited rides for an entire day, with Uptown and Downtown loops to choose from. You can stay on for both loops to cover much of your day. Otherwise, hop off where you’d like to explore more.
- The RIDE. A themed bus tour that’s part comedy act, part theatre, and part tour, The RIDE is perennially popular with visitors to NYC. They’ll cover city hotspots in 75 minutes for one hilarious experience.
Chicago
- Hop-on Hop-off Bus Tour. A hop-on hop-off option from Big Bus Chicago, this loop includes 14 different stops throughout downtown Chicago. Stop at places like Museum Campus, Willis Tower, and Millennium Park.
- Scenic North Side Tour. An exhaustive tour, the scenic North Side Tour covers landmarks and hotspots in Chicago that aren’t typically covered by downtown tours. It’s a two-hour sightseeing tour that covers everything from Water Tower Place Mall to Wrigley Field.
Cruises
With Chicago’s lakefront location and Manhattan being an island, both cities are popular for their multiple cruise options. Here are some of the top cruises in each city to help you decide which sound the most appealing.
New York
New York
- NYC Landmark Cruise. This landmark cruise is a 90-minute excursion around the waters of Manhattan, showcasing everything from the Brooklyn Bridge to the Statue of Liberty. It’s ideal for photo ops and offers informative narration alongside your views.
- Liberty Cruise. A 75-minute boat tour around Lower Manhattan and Ellis Island, the Liberty Cruise is a specific focus on Liberty Island and its environs. This cruise option is best for those who want a focused excursion.
Chicago
Chicago
- The Architecture River Cruise sails along the Chicago River is a 75-minute trip that encompasses time on all three branches of the river. The focus is on city landmarks that have been constructed or rebuilt after the Great Fire of 1871. Also great for photos.
- Lake Tour. The Lake Tour of Lake Michigan is a 45-minute cruise that showcases all of the city skylines from Navy Pier to the Hancock Tower and beyond. Informative narration will highlight everything of note, and you’ll get excellent lake view photos.
Cuisine
Cuisine
Remarkably enough, both cities are famous for their unique styles of pizza.
New York-style pizza has a thinner crust but is not thin and crispy like a brick oven pizza. It has lots of cheese and is a bit floppier in terms of the eating experience. You’ll find authentic slices all over the city - remember to fold it in half while eating!
Chicago-style pizza is a deep-dish style, usually a few inches thick, and served in a cast-iron pan. It's also topped with plenty of gooey cheese and plenty of meaty toppings. There are several famous places in the city to find this delectable specialty - check out Gino’s East or Lou Malnati’s.
Both cities are also known for their international populations and global influence. Therefore, you can find practically any culinary style in either city. Whether you’re looking for some ramen, sushi, or filet mignons, you’ll find all of it in Chicago or NYC.
As far as cuisine goes, your point of comparison is probably going to be price. Chicago has many Michelin-star restaurants with nearly astronomical prices. However, you’re still more likely to find more affordable haute cuisine in the Windy City than you are in NYC.
Can't choose? No need, see it all with Go City®
Admission to most of these top New York and Chicago attractions is included with Go City. You can save on admission to these and many other popular activities, tours, and cruises. These easy digital passes are a great way to see the best each city has to offer and save up to 50% on admission vs paying at the gate.
✈️ >> Buy the Go City® New York pass and the Go City® Chicago pass
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