Chicago vs. New York City

These two great American cities are worthy of all the tourist traffic they generate year in and year out. New York has been an iconic destination for generations. Chicago is easily one of the most global cities in the country.

By Katie Sagal
Published: May 16, 2024
Chicago vs New York

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.

✈️ >> Buy the Go City® New York pass and the Go City® Chicago pass

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 observation deck

 

  • 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 observation deck
  • 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.

Moma
  • 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

Art institute of 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

American Museum of Natural History
  • 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

field-museum-chicago-on-summer-day
  • 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

Big Bus

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

luxury-cruise-ship-sailing-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 river cruise
  • 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

Pizza in New York

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

Share your adventure with us

Tag @GoCity or use the hashtag #GoCityPass in your vacation photos and we'll see if we can feature you on our page. Follow the Go City Instagram and Facebook pages for competitions, special offers, events, and inspiration for your chosen destination, too!

Katie Sagal
Go City Travel Expert

Continue reading

Blog

New York in April

April is undoubtedly one of the best times to visit New York. Whilst the city isn’t exactly known for its balmy winters, millions make the expedition each year to experience its wonderful springtime. From beautiful gardens and parks to fantastic Easter celebrations, this place has it all. If you’re looking for some inspiration when it comes to planning a trip to the Big Apple, check out our list of the best things to do in the warmer months. To make your money go further, have a look at our Explorer Pass and All-Inclusive Pass. With Go City, you can see more, for less. Taste the City Music festivals provide an experience like no other. To grab a slice of the action, head down to the Brooklyn Folk Festival. True to its name, this event features the very best of American and world folk music across a wide variety of genres, including blues, bluegrass, Latin & Balkan music and much more. In addition, there are vocal and instrumental workshops, film screenings, and jam sessions to sink your teeth into. Ever dreamed of taking a sneak peek at the newest and most innovative automotive trends? Well, as it turns out, you can! The perfect activity for a somewhat disagreeable afternoon, the New York International Auto Show presents the very best that the automobile industry has to offer in a comprehensive and engaging way. A total car-lovers’ dream, this 10-day auto consumer extravaganza features everything from classics and luxury dream cars to new models and even futuristic concept vehicles, right in the heart of Manhattan. With almost 1,000 of the world’s most stunning vehicles on display, we promise you won’t leave bored! New York presents a wide variety of options when it comes to all things food. A total must for meat lovers, Brisket King is a culinary festival featuring 20 chefs and pitmasters serving up their best mouthwatering creations. Enjoy the juiciest brisket in Brooklyn prepared in every way thinkable as well as craft beer, hard cider and spirits. After the brisket king is crowned, guests are encouraged to stay for the after-party and – you guessed it – more food! Sounds pretty good to us. Soak up the Spring There’s no shortage of great outdoor attractions all over New York. Stretching through the Meatpacking District and along the West Side of Manhattan, the High Line is a linear park and popular city landmark, welcoming a whopping 8 million visitors each year. Perfect for a lazy springtime stroll, the structure was redesigned in 2006, and now serves as a living system for a wide variety of plants and animals. Go for a picnic, admire the majestic city skyline or sit back and enjoy the sunset – the choice is yours! Another one of our favorite places to see in the springtime is the Conservatory Garden in Central Park. Since first opening in 1937, the spot has become a favorite for visitors from all over the world and is now known as one of the most noteworthy public gardens in New York City. The garden is comprised of three areas, each with a specific design: the English-style South Garden, the French-style North Garden, and the Italianate Center Garden. April is the perfect time to amble through the winding pathways and admire the waterlily pools and stunning floral displays along the way. If you're travelling during Easter, you might want to check out the many egg hunts taking place around the city. At the beginning of the month, the Children’s Museum of Manhattan throws its own event with egg sculptures hidden throughout the institute. Another great option is the Rockefeller Center’s Inaugural Easter Egg Hunt with live musical performances, Easter bonnet making stations, prize giveaways, and more. Meanwhile, those who want to get in touch with their inner child should consider looking into Central Park’s Easter Egg Scavenger and History Hunt. Get Cultured For those rainy spring afternoons, it just makes sense to have a good backup plan. Eclectic and full of character, Chelsea Market is a great place to visit with friends and family. Located right in the center of the Meatpacking District, this fun attraction is known for its seriously tempting food hall, unique stores and live music performances. Grab a bite to eat, weave through the interesting stalls, and pick up some one-of-a-kind souvenirs for loved ones along the way. The market’s bohemian flair and laid-back atmosphere puts it in a class of its own. Those who are looking to celebrate Easter in style should definitely consider checking out the Easter Parade and Bonnet Festival. Beginning as a spontaneous event in the 1870s, this fun annual procession began as a means for the city’s most fashionable dressers to exhibit their impressive festive finery. Though the event draws in smaller numbers nowadays, New Yorkers participate each year with great enthusiasm and increasingly outlandish costumes. Creative and eccentric, the event is a unique cultural expression of Easter which you won’t see elsewhere. Spring weather can be a little touch-and-go - still, New York presents a wide array of fantastic indoor activities right at your disposal all throughout the month. Those who are looking to soak up the culture of the city should consider checking out Tribeca Film Festival. Set up by Robert De Niro himself, this event was developed as a way to restore the Tribeca neighborhood of Lower Manhattan following the 9/11 attacks. The event attracts around 150,000 attendees each year and is widely considered to be one of the most prestigious film festivals in the area. Showcasing a diverse selection of feature films, short pictures, and documentary pieces, there’s a little something for everyone here. Those who are especially interested can also attend immersive programming and Q&As with relevant storytellers. New York in the spring is a beautiful time for many reasons. The weather is warm, the streets are bustling with life, and the city is in full bloom! But the best part? No matter where your interests may lie, you’ll always be able to find fun things to do. From cherry blossom peeping at the Conservatory Garden to seriously tempting food festivals in Brooklyn, there are so many great things to do in the city for every type of traveller! Make the most out of your visit with our All-Inclusive pass and Explorer pass. For more information, check us out on Instagram and Facebook.
Sarah Harris
Blog

New York in October

Searching for interesting activities and exciting events in New York this Autumn? Well, you’ve come to the right place. Whether you’re planning a fun family trip or travelling solo, the city provides a wide array of engaging experiences to keep you busy in the fall. Those looking for stunning architecture, delicious food and world-class art will not be disappointed. If you’re planning to make the trip, read on for some of our top things to do in New York during October. Explore the City If you’re looking to avoid those rainy Autumn afternoons, don’t worry – we’ve got you covered. Built into a stunning building overlooking the Hudson River, The Cloisters specializes in European medieval art, with an emphasis on the Romanesque and Gothic periods. A total must-see for art lovers, the repository holds an expansive collection of over 5,000 paintings, sculptures, tapestries and more. Fascinating and exciting, this place provides a delightful educational experience for those of all ages. Those who are interested in exploring the history and culture of New York might want to check out the Merchant’s House Museum. Though once serving as a home to the Tredwells, a prospering merchant-class family, this fully intact row house now seeks to provide an intimate glimpse into Old New York. Listed as a National Historic Landmark, this small venerable building is considered to be one of the best remaining examples of Greek Revival and late-Federal architecture. Visitors can take self-guided walking tours to view the elaborate plasterwork and rare art pieces whilst learning more about those who lived there. Don’t let the weather ruin your vacation. If you’re wanting to stay dry whilst soaking up some culture, why not check out the New York Film Festival? Standing out amongst other fantastic attractions in the city, this event is one of the longest-running and most prestigious film festivals in the United States. Screening a broad selection of feature films, short pictures, and documentary pieces, there's more than enough to choose from. Those who are particularly interested in learning more about cinema can also catch special events, masterclasses and talks. Find Interesting Activities There’s always a fun event to attend in the city. Attracting hundreds of thousands of visitors each year, the New York Wine and Food Festival brings together some of the world’s most celebrated chefs and sommeliers together for this annual four-day extravaganza. A great stop for all foodies, the event offers a wide array of culinary events, including walk-around tastings, intimate dinners, culinary demonstrations and late-night parties. Elegant, relaxing and affordable all at once - what's not to love? The city presents a wide variety of indoor attractions once the weather starts to cool down. If you’re interested in pop culture, you might want to check out New York Comic Con. Since establishing itself in 2006, the event has grown to become one of the biggest Comic Cons of them all, celebrating all things nerdy! The festival features everything from exciting workshops and artist and celebrity Q&A panels, to lightsaber battles and cosplay contests right in the center of Manhattan. With previous guests like Adam West, David Harbour and Bryan Cranston, you won't want to miss out on this one! How could we talk about October in New York without mentioning Oktoberfest? Running from the start of the month, this traditional Bavarian festival is undoubtedly one of fall’s finest delights. Celebrations take place across all five boroughs at various restaurants, bars and outdoor spaces. Soak up the suds at the biergarten, dig into a hot bratwurst straight off the grill or enjoy an authentic music performance – the choice is yours! Arguably, one of the greatest things about New York City is its delicious gastronomic offerings. Those who are looking for a taste of the city should head down to the Brooklyn Bagelfest for an unparalleled cultural and culinary adventure. Enjoy the best bagels from a wide variety of favorite New York vendors, as well as craft beer on tap. As if that wasn’t enough, the festival also features bagel-themed activities, art and music. Get Festive October is Halloween season, and we refuse to just ignore it. If you’re looking to kick the spookiness into high gear, you might want to look into Central Park’s Pumpkin Flotilla. Amongst the best fall foliage in the city, you can hear ghost stories, check out a costume parade, and carve out a delightful pumpkin! After the festivities, watch fifty gourds glow up the Harlem Meer at twilight. Feel free to dress up for the occasion! Another one of our favorite October events is the Village Halloween Parade. Drawing in millions of spectators each year, the event is recognized as the world’s largest Halloween procession. Billed as ‘’New York’s Carnival’’, the spectacular parade features around 50, 000 costumed participants, exceptional marching bands, remarkable floats and enormous puppets. A little quirky and a whole lot of fun, the festival delivers a one-of-a-kind holiday experience to remember for years to come. If you were thinking that Halloween was the only way to celebrate in New York in October, you were wrong! A national holiday for many, Columbus Day celebrates the discovery of the New World whilst also serving as an important festival for the Italian American community. Drawing in around a million spectators each year, the Columbus Day Parade brings a whole host of family-filled fun, complete with colorful floats, lively musical performances and dancing. Those who are travelling during the federal holiday should keep in mind that other attractions may be closed for the rest of the day. The East Coast dazzles all year round, but we particularly love New York in the vibrant autumn months. The air is brisk, the colors are changing, and the city comes alive with a whole host of seasonal experiences. Whether you're looking for fun Halloween events like the Pumpkin Flotilla, or something cozier like a quiet museum day, the city presents a wide array of engaging experiences to keep you busy in the fall. Explore the city to its maximum potential with Go City’s All-Inclusive Pass or Explorer Pass. If you’d like to know more, connect with us on Instagram and Facebook.
Sarah Harris
Blog

New York in May

May is a wonderful time to visit New York and see the sites, find some exciting activities, and immerse yourself in the culture of the city. As the weather starts to warm up, the area will be flourishing with exciting festivals, fun pop-up markets and delightful events held in NYC parks. So, we’ve rounded up our favorite springtime ideas for those who are thinking about making the visit — from Cinco de Mayo festivities to extravagant flower shows, we’ve got you covered. With Co City, you can create memories for years to come. Get to Know the City There’s nothing like a day at the ballpark, right? Once spring kicks off, the balmy weather serves as the perfect backdrop for the start of the season. Those who are interested in catching a Big Leagues game should be able to book tickets to the Yankees or Mets online – just be sure to book early, since these things sell out fast! We can almost taste the cold beer on our lips and feel the sun on our faces. Another one of our favorite things to do in the city for May is attending Frieze New York. A total must for art lovers, the event seeks to celebrate the best work of international historical and contemporary artists. For five days each year, The Shed fair features works from over 1,000 artists and 200 international galleries for a broad audience. In addition, the festival features a great program of just commissioned works, films and talks. If you’re looking to experience the city through its food, you might be interested in the next item on our list. The perfect day trip for any gastronome, the Ninth Avenue International Food Festival offers a diverse range of cuisines from popular local vendors. Whether you’re looking to try out traditional street fair treats or taste cuisine from around the globe, this event has it all. In addition, the festival features two stages of live music, food contests, as well as over 200 vendors selling unique arts and crafts. Find Interesting Activities Since New York is known for its exceptionally multi-ethnic population, it seems only fitting that the city observes Cinco de Mayo in style. Held annually in the fair springtime weather, a vibrant parade makes its way down Fifth Avenue and leads towards festivities in Sunset Park. In addition, you should be able to celebrate at various bars and restaurants across all five boroughs with live Mariachi music, traditional dancing, and delicious Mexican food. Bursting with excitement, New York is the perfect tourist destination with a plethora of attractions for you and your loved ones. Since its establishment in 1982, Fleet Week has served as an annual celebration of the US Navy, Coast Guard and Marine Corps. The annual week-long tradition kicks off with a flotilla of naval vessels docking in at the New York Passenger Ship Terminal on the Hudson River. Those who are looking to join in on the fun should be able to find a string of parties all over the city, with dress-up, live musical performances, and an abundance of drink! An unusual and exciting occurrence, this event is nothing but fun! If you’re travelling during Memorial Day weekend, you might want to check out some of the festivities going on in the city. As with any big federal holiday, you won’t have to look far to find the parade, which kicks off at 11 A.M. on Third Avenue each year. In addition, the city offers some great ways to pay tribute to America’s fallen soldiers, including the New York Philanthropic Memorial Day Concert, Intrepid Museum’s Free Movie Night, and Central Park walking tours, which take you through a number of fountains, monuments, and sculptures that honor past lives. And as if that wasn’t enough, you should be able to find many restaurants and bars across the city holding their own special events. Try Something New Why go to the theater when you can watch Shakespeare right in the middle of Central Park? That’s right, you heard us. Set up against the magnificent natural splendor of the park, The Public Theater provides admission-free world-class entertainment – honestly, we couldn’t think of a better way to spend the evening. With past cast members like Meryl Streep, Al Pacino and Denzel Washington, we don’t think you’ll want to miss out on this one. May means Mother's Day – and what better way to celebrate this major holiday than with a flower show? Running from 2nd-26th of May, Macy’s spectacular two-week exhibit features beautifully manicured living sculptures, inspired by a different theme each year. Completely free to the public, the vibrant display is open for viewing during the store’s regular hours. Totally iconic and incredibly Instagram-worthy, we highly recommend noting this one down. New York is home to some of the most renowned cultural amenities in the country. Situated along Fifth Avenue, the Metropolitan Museum of Art is one of the largest and finest creative institutions in the Western Hemisphere. As stunning as it is fascinating, the repository features more than two million works of art spanning over 5000 years. Spring is an especially great time to visit, since the Cantor Roof Garden Bar will be open to all visitors. Granting fantastic views over Central Park, this is undoubtedly the perfect place to sit and relax after a hard day at the museum. May is the perfect time to visit the Big Apple. The weather is fresh, the flowers are in bloom, and as always, the city presents endless exciting attractions to its visitors. Whether you’re a foodie, an art lover, or a sports fan, there’s a little something for everybody here. Celebrate Cinco de Mayo to its fullest, try out the area’s rich culinary offerings, or enjoy Shakespeare under the stars – the choice is yours! And now, you don’t have to miss out – with our All-Inclusive Pass and Explorer Pass, you can find an exhaustive array of things to do, for cheaper. If you’d like to know more, connect with us on Instagram and Facebook.
Sarah Harris

Have a 5% discount, on us!

Sign up to our newsletter and receive exclusive discounts, trip inspiration and attraction updates straight to your inbox.