The best stops on a road trip from NYC to Chicago

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August 7, 2020
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Road tripping from NYC to Chicago can be a fun travel plan with plenty of fun stops in between. Here are our best suggestions.

New York City and Chicago are two of the most popular cities to visit in the United States. If you live in NYC, you can easily travel and visit Chicago. There are three main ways to get to Chicago: by plane, train, or car. How far are the two cities from each other? What are the differences in time and distance between each travel option?

According to Distance Between Cities, NYC and Chicago are about 711.04 miles apart if you connect the two places directly without accounting for the routes you would have to take. The city that is halfway between New York and Chicago is North Jackson, Ohio.

If you choose to fly to Chicago from NYC, it will take around 2 hours for a nonstop flight. On the other hand, it will take around 3 hours and 45 minutes for connecting flights. Going by train to Chicago will take you 22 hours and 46 minutes. Assuming you start at Pennsylvania Station in NYC and transfer three times to other lines.

If you want to enjoy the adventure of traveling from NYC to Chicago by car, you would have to travel around 796 miles. Additionally, the NYC to Chicago drive will take around 12 hours and 13 minutes without any stops or sightseeing in other cities. Depending on your car, the cost of gas will be around $50-$97. According to Google Maps, the main route you would use to get to Chicago is the I-80/I-90.

We planned our trip from 421 Hudson Street, #610 located at West Village, Manhattan in NYC to 130 North Garland Court, #1612 in The Loop, Chicago. We chose these listings because they are both located in the hustle and bustle of the city.

The West Village duplex condo in Manhattan is located on the western side of NYC and is less than 10 minutes away from the main highway.  The building amenities include on-site valet service so you wouldn’t need to worry about searching for parking. The Chicago apartment is in a landmark district so the area is filled with unique architecture that is protected.

Additionally, the space comes with one heated garage parking space so you don’t need to worry about where to leave your vehicle.

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Things to do between New York and Chicago

Many people like to compare NYC and Chicago and claim one city is better than the other. But why pick just one when you can visit both? It’s as simple as road tripping from NYC to Chicago.

Even better, there are plenty of fun places to visit on the way and things to do between New York and Chicago. Here are just some ideas for stops NYC to Chicago when you start planning your road trip.

Start: New York City, NY

421 Hudson Street, #610 West Village, New York ($14,000) – 2 beds, 2.5 baths, 1,800 sqft

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421 Hudson Street, #610 West Village, New York

Stop 1: Lancaster, PA

The first stop is around 2 hours and 52 minutes into the trip at Lancaster, Pennsylvania. It is a city around 163 miles away from NYC. Lancaster is located in South Central Pennsylvania and is one of the oldest inland towns in the U.S.

The city is best known for being a hub for Pennsylvania’s Amish Country and you can even visit and tour the Amish Village and 1840 Amish farmhouse. There are plenty of historical landmarks to visit such as the Fulton Opera House and Central Market.

Lancaster also has a thriving arts community with a variety of art galleries and museums. A few you may find interesting are the Demuth Museum, Gallery Row, and  Lancaster Museum of Art.

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Stop 2: Hershey, PA

The next stop is Hershey, Pennsylvania. It is just 28.9 miles away from Lancaster, PA and is around a 36 minute drive. Hershey is an unincorporated community and is best known as the home of The Hershey Company.

The community has various chocolatey adventures in store such as the Hersheypark, The Boardwalk At Hersheypark, and Hershey’s Chocolate World Attraction. Whether you enjoy rides and rollercoasters, dipping in a pool during warmer weather, or enjoying various chocolatey snacks, this community offers all of the above.

Other things you can enjoy in this community includes the Hersheypark Stadium and Hershey Gardens. If you want to know all about the history of this area, you can take a trip to The Hershey Story Museum.

Stop 3: Pittsburgh, PA

The third stop on this road trip is 215 miles away at Pittsburgh, Pennsylvania, a 3 hour and 29 minute drive from Hershey. It is a metropolitan city that serves as the anchor of Western Pennsylvania.

Pittsburgh has a rich history in arts and culture and there are plenty of art museums, theaters, and attractions to visit. This includes the amusement park Kennywood, Phipps Conservatory and Botanical Gardens, and Pittsburgh Zoo and PPG Aquarium.

A few major art museums in the area are the Andy Warhol Museum, the Carnegie Museum of Art, and the Mattress Factory. Additionally, if you time your trip accordingly, you can join in on their annual Three Rivers Arts Festival.

stops on the way to chicago

Stop 4: Akron, OH

This next stop takes us out of the state of Pennsylvania into Ohio. Akron, Ohio is a 110 mile drive away from Pittsburgh and takes around 1 hour and 49 minutes.

Akron is the fifth largest city in Ohio and is on the western edge of Glaciated Allegheny Plateau. There are various attractions you can visit in the city such as the Akron Art Museum that showcases art produced since 1850, the Stan Hywet Hall and Gardens, the Akron Civic Theatre for live performances, Lock 3 for festivals and events, and Akron Zoo.

The community also hosts an annual festival called Art in the Square that features local artists and musicians.

stops on the way to nyc

Stop 5: Cleveland, OH

The next adventure in the state of Ohio is Cleveland. It is 39.4 miles away from Akron and is around a 43 minute drive. This major city is located on the southern shore of Lake Erie and is the second largest city in Ohio.

Cleveland has many attractions to explore such as Playhouse Square, Rock & Roll Hall of Fame, A Christmas Story House, Cedar Point Amusement Park, Cleveland Botanical Garden, Cleveland Metroparks, and various art and history museums.

There are also various authentic experiences you can find in the city like exploring the city’s various breweries and go whiskey tasting.

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Stop 6: Fort Wayne, IN

This sixth stop in this road trip adventure takes us into the last state before Illinois. Fort Wayne, Indiana is 200 miles away from Cleveland, OH and is around a 3 hour and 35 minute drive. This city is located in northeastern Indiana and the cultural and economic center of the area.

Fort Wayne has a Cultural District that is home to the Embassy Theatre, Fort Wayne Museum of Art, Fort Wayne Dance Collective, and various other cultural institutions. Some other attractions you may enjoy are Science Central and the Foellinger-Freimann Botanical Conservatory.

If you’re lucky, you may just be in town when the city throws one of its annual cultural festivals that celebrate ethnic food, dance, music, and art.

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Stop 7: Michigan City, IN

The last stop on this road trip is Michigan CIty, Indiana. It is 116 miles away from Fort Wayne and is around a 2 hour and 11 minute drive. The city is located in LaPorte Country and is approximately 50 miles east of Chicago.

Michigan City is home to the Old Michigan City Light, the Pullman-Standard rail car plant, and has one of the nation’s oldest active municipal bands. Some attractions to visit in this city are Washington Park, Beach & Zoo, Hesston Steam Museum, Barker Mansion, Blue Chip Casino, Friendship Botanic Gardens, and Rosey’s Berry Farm.

Destination: Chicago, IL

130 North Garland Court, #1612 The Loop, Chicago ($3,200) – 2 beds, 2 baths, 1,100 sqft

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130 North Garland Court, #1612 The Loop, Chicago

With so many cities and attractions to explore between the two cities of NYC and Chicago, you’ll never get bored during a road trip.

Looking to live in Chicago or NYC? Localize has you covered. We have insights on all listings in NYC and Chicago so you can find your perfect home.

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