Get Ready for a Road Trip from the Windy City to the Big Apple

August 22, 2021
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Chicago is a large city with a friendly midwestern appeal that offers tourists so many things to do, from boating on Lake Michigan, shopping on North Michigan Avenue, or catching a Cubs or White Sox. But if you decide to take a road trip to New York City to enjoy first class museums, amazing dining options, and some must-see landmarks, you’re in for a fun journey with lots to see on the way. So let’s get our bags packed and fuel up the car, because here are the top places to see on your Chicago to New York City road trip!

Shedd Aquarium 

Learn all about marine life from all over the world

1200 S. Lakeshore Dr. | Chicago, IL | sheddaquarium.org

Chicago has so many amazing places to visit, but if you only have time to see a few, the Shedd Aquarium should definitely be one of them. Housed in a stately neo-classical building since the early 20th century, this aquarium was designed to impress visitors as much as it is to educate them. Where else can you come face to face with creatures such as beluga whales, turtles, and penguins in such an informative and engaging environment? The Shedd has exhibits ranging from a Carribean reef, an Amazon river bed, and the Great Lakes, and offer tourists a look at environments and animals they might not otherwise encounter.


You can even come face to face with stingrays, or see the dolphins play in the oceanarium! The Shedd is also a partner with organizations across the world working to conserve species and habitats, so these animals and their ecosystems are around for years to come. There is so much to see and do here, you’ll feel as though you might need a couple of hours! Of course, don’t forget to check out their gift shop for an array of eclectic gifts to start your trip right.


Indiana Dunes National Park

Enjoy the views and explore this beautiful park!

1215 N. State Road 49 | Porter, IN | nps.gov


The Indiana border isn’t far at all from Chicago, and in what seems like no time, you’ll be arriving at your next destination, the Indiana Dunes National Park. You’ll love the amazing views of Lake Michigan and will definitely enjoy the quiet beauty of the dunes. This park has over 15,000 acres of dunes, marshlands, and forests, with the tallest dunes in upwards of 200 feet high, and valleys full of wetlands. This interesting land was created by glaciers and their retreat over 14,000 years ago, and is such an amazing sight to see. Here you can explore the park on your own and choose one of the many nature trails to catch glimpses of native birds and animals.


After you explore the seashore, stop at one of the historical landmarks located within the park, such as the Bailly Homestead or the Chellberg Farm where you can explore the house of an 18th century fur trader or an authentic late 1800s farmhouse! 

Cooke-Dorn House

Explore a historic home in downtown Sandusky

1415 Columbus Ave. | Sandusky, OH | ohiohistory.org


As you enter into Ohio, you’ll eventually come across the beautiful lake town of Sandusky, where there is a lot to see and do. Make it a point to stop at the historical Cooke-Dorn House, which was originally built in 1844 for Eleutherus Cooke, who was Sandusky’s first lawyer and who also served in the U.S. Congress. It was subsequently bought by the Dorns in 1953 and it remains a wonderful example of mid-century decor.. This museum features many interesting items from the 19th century as well as the 20th, and also has gardens you can tour as well! 


While you’re stopped in Sandusky, it’s just a hop, skip, and a jump to the islands of Lake Erie. Catch a ferry and explore Kelley’s Island, Put-in-Bay, or Middle Bass. These islands are filled with their own cute shops and fun eateries, and it’s very easy to lose yourself exploring them!


Rock and Roll Hall of Fame

See if your favorite musician has made it into the hall of fame!

1100 E. 9th St. | Cleveland, OH | www.rockhall.com


When you reach the other end of Ohio, you’ll run into the lake town of Cleveland, which is a fun city to spend a couple of hours in! You can tour their art museum, visit one of their many breweries, or spend time doing some shopping. But the one thing everyone who comes to Cleveland must do, is visit the Rock and Roll Hall of Fame. Opened in 1995, this Cleveland landmark is a shrine to everything rock and roll, and no matter who your favorite band is--and regardless if they are in the hall--you’re going to have an amazing time.


Each year artists are inducted into the hall who have made a significant contribution to rock and roll. Currently some of the highlights of the hall of fame are the Beatles’ Space Exhibit, David Bowie’s Moonlight Tour Suit, the Supremes’ dresses, and Michael Jackson’s glove. This attraction has so much more to offer even the most casual music fan, and it really is something everyone should see.


Niagara Falls State Park

Take in the view of one of the most impressive waterfalls in the world

332 Prospect St. | Niagara Falls, NY | niagarafallsstatepark.com


If you haven’t already had the pleasure of seeing Niagara Falls, then this is a must-visit on your way to New York City. There are plenty of places to get some amazing Insta-worthy photos of the massive falls, but depending when your road trip takes place, it could get a little crowded. Some of the best times to visit the falls are on the weekdays, so if this is possible, it’s highly recommended. Of course you’ll want to take a tour, and The Maid of the Mist is by far the most popular. This boat tour will get you safely as close as you can to the falls-- so prepare for some loud water! 


You could also explore the Niagara Gorge, and walk as close as you dare to the thundering Bridal Veil Falls. Not to worry, they’ll provide you with a slicker and sandals so you can safely descend the staircase towards the falls. There is also a highly informative The World Changed Here pavillion where you can discover why people have always been drawn to the falls, and the ways they tried to harness its power!


Seneca and Cayuga Finger Lakes 

Explore one of the most beautiful places in New York!

New York | fingerlakes.org


Located on a large portion of upper New York and between the cities of Rochester and Syracuse are the Finger Lakes. The lakes are a set of 11 deep glacial lakes that are much longer than they are wide, which gave them the name the Finger Lakes. The two largest lakes are Seneca and Cayuga Lakes, of which Seneca is one of the deepest in the U.S., at 618 feet deep. There are plenty of wonderful parks surrounding these lakes where--depending upon the weather--you can rent a boat, take a lake tour, hang out at the beach, or just stroll along the sand. These Finger Lakes are a nice relaxing way to see some of the natural beauty of New York.


While you’re in the area, consider stopping off at the small town of Auburn and visit the Harriet Tubman Home where you can see where this amazing woman who led so many enslaved people out of slavery settled down. Or if you happen to be traveling from June-October, you could visit the Strawberry Fields Hydroponic Farm, also in Auburn, where you can pick dirt-less strawberries to take with you!


Adirondack Park

View old growth forests and spend some time outdoors

115 Tall Pine Rd. | Northville, NY | apa.ny.gov


As you gradually move out the Finger Lakes region you will most certainly know you have arrived in the stunning Adirondack region of New York. At the center of the park is the Forest Preserve, which according to an 1885 act of the NY legislature, specified that this region should remain forever wild, and never be sold or used in any commercial endeavor. This means that the forests in this park include old growth forests that are seen almost no where else in the eastern part of the U.S. It is also the largest park in the U.S., with about 6 million acres in total, and bigger than the Everglades, the Grand Canyon, and Yellowstone parks combined. 


There’s a lot of recreational opportunities to explore, such as hiking, bird watching, canoeing, fishing, or rock climbing, so if it’s an outdoor adventure you’re after, this is the place to do it. While you’re in the region there are also a host of historical sites you might want to visit, such as the Frances G. Kinnear Museum, where you can tour an 1880s home and view the vintage furniture and clothing!


Vanderbilt Mansion National Historic Site

Visit one of the oldest Hudson River estates

119 Vanderbilt Park Rd. | Poughkeepsie, NY | nps.gov


If you’re curious to see how the wealthy Vanderbilts lived in the 19th century’s Gilded Age, the Hyde Park mansion should be next on your stop. You can start at the visitor’s shop and sign up for a tour, which will take you to both levels of the mansion, as well as the basement. It’s a wonderful example of how the elite from another age lived. There are also outdoor gardens that you can stroll around at your leisure, or head head towards the river to get some amazing photos of the view of the Hudson.


Because this area is also a national park, you can feel free to walk the grounds and even set up a picnic if you’d like. There are all kinds of beautiful flowers and native animals, so make sure to have your camera ready!


Statue of Liberty

View the iconic symbol of arriving in New York City

Liberty Island, NY | www.nps.gov


Once you’ve made it to New York City, there are so many things you’re going to want to do! Make sure that at the top of that list is stopping to view the Statue of Liberty National Monument. Statue Cruises operates ferries that will get you to Liberty Island, so you can fully take in this iconic landmark. Once you’re there, you can walk around the grounds, and even climb to the top of Lady Liberty--but make sure to have your walking shoes on, since there are 539 steps to the top!


When you’re done touring the statue, head over to the museum, where you can learn the history behind the statue and how the U.S. and France worked together to create a lasting image of friendship, and also view the original 1876 torch that Lady Liberty held. Make sure to check out the rooftop deck of the museum, which offers some stunning views of the statue and New York Harbor!



Metropolitan Museum of Art 

Spend as much time as you can at this prestigious museum!

1000 Fifth Ave. | New York, New York | metmuseum.org


There are a multitude of amazing museums located in New York City, but if you have time to do only one of them, make it the Met and you will not be dissapointed! Where else can you experience over 5,000 years of art from around the world, all in one place? No matter what your favorite type of art is--sculpture, modern, classical, or textiles--you’ll find it in abundance at the Met. You can choose to structure your visit according to regions of the world--such as Europe, Africa, or Asia-- or you can choose to just wander the halls at random, and see in what direction you’re pulled!


There is also an amazing cafe inside the museum with views out into Central Park, and a simple menu that lets you concentrate on the artwork that surrounds you instead of deciding what to try to for lunch. As you make your way through the halls, you’re sure to see art students who are hard at work, sketching away at their versions of these timeless works of art!


The trip from Chicago to New York City is a long one, but thankfully there are a lot of wonderful places to stop along the way. Where do you like to stop on your trips from Chicago to New York City? Let us know in the comments!


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