7 Essential Stops Driving from Chicago to New York

A Chicago to New York Road Trip Itinerary Perfect For Families

If you’re in the mood for bustling cities, resort towns, and lakefront communities, a road trip from Chicago to New York might just be exactly what you need. 

A drive from Chicago to New York will take you through six states, passing incredible scenery, including the Great Lakes and several historic cities. 

Along the drive, you’ll get to experience some of the best Illinois, Indiana, Ohio, Pennsylvania, New Jersey, and New York have to offer. Great food, lovely landscapes, and incredible cultural offerings are just a small part of what this road trip has to offer! 

If you’re ready to take the road and set out on a road trip from Chicago to New York City, let us help you plot the route. Simply follow our itinerary, which includes the best stops and unforgettable attractions to check out as you drive from Chicago to NYC. 

The Best Driving Chicago to New York City Itinerary 

What is the Distance From Chicago to NYC? 

The distance from Chicago to NYC is 790 miles, which takes between 12 and 13 hours of pure driving. You’ll be moving about half of the way on I-90 east and the second half on I-80 when driving from Chicago to New York by car. 

The 790-mile road trip from Chicago to New York City can be done in a little over 12 hours, but the idea is to take a few days and stop along the Great Lakes, Pittsburgh, and Philadelphia, as well as check in at a couple of beautiful national parks on the way. 

Along your Chicago to NY drive, you’ll be passing from a big metropolis to small towns and lakeside villages in a smorgasbord of stunning landscapes and must-see sights before you arrive at the Big Apple. 

How Long Do I Need to Drive from Chicago to New York? 

Your road trip from Chicago to NYC can take from a couple of days to two or three weeks. It all boils down to how much time you have available. We strongly suggest spending a couple of weeks in order to have plenty of time to visit some of the cities’ highlights while leaving room to enjoy what the smaller towns have on the menu. 

If you have the time and want to shake it up a little, you can take a slightly more scenic 900-mile route, with a few detours and byways that will give you a few more things to do and see along the way. 

If you drive direct without stops, Chicago to New York City will take you around 12 hours.

Best Time Of Year to Drive from Chicago to NYC 

The Midwest and Northeast regions of the United States have somewhat extreme weather. If you’re not keen on sweating out the heat or getting stuck in a winter storm, your best bet is to plan your road trip from Chicago to New York City in the late spring or early summer. 

Of course, some attractions are on offer only during the summer and winter months, so it really depends on what exactly you want to do during your getaway. Early fall is also a good option if you’re not into crowds, especially when you consider fall foliage in that region of the US is stunning. 

Best Stops on a Chicago to New York Road Trip 


Chicago is the biggest city in the Midwest and the third in size in the US. The Windy City is famous for its skyline full of skyscrapers, baseball, and great hot dogs. You could spend a week or two exploring everything on Windy City’s menu, but a couple of days should be enough to experience the main highlights. 

For spectacular aerial views, Chicago offers two observation decks situated in two of the most famous skyscrapers in the world – Skydeck, which is on the 103rd floor of the Willis Tower, and 360 Chicago on the 94th floor of the John Hancock Building. 

USA Chicago to New York - Chicago

Millennium Park is a must-see in Chicago. This attraction is set above The Art Institute of Chicago and homes incredible art, architecture, and landscaping. 

Traveling with children, be sure to take them to the Field Museum of Natural History, one of the Windy City’s most iconic museums. They’ll also have a blast at the Museum of Ice Cream! 

Lake Michigan 

The first leg of your journey, once you leave Chicago, will take you around the southern part of Lake Michigan, the second largest of the Great Lakes. 

A great way to experience the lake is to stop at Portage, which is only 41 miles from the Windy City. Incredibly enough, you’ll have entered the state of Indiana by driving that short distance on I-90! 

USA Chicago to New York - Lake Michigan

Portage is most famous as a gateway to the Indiana Dunes National Park, which is worth paying a visit. Here, you can hike the three-dune 1.5-mile challenge or simply relax and swim at the beach.  

There are plenty of boarding options both at Indiana Dunes and Portage, in case you decide to make it an overnight stop or squeeze in a few days of lake vacation on your way to New York. Portage Lakefront & Riverwalk’s enclosed pavilion offers food services and restrooms. 

Cleveland – Lake Erie, Ohio 

The next stop is Cleveland. You’ll be leaving Lake Michigan behind and traveling east on I-90 for 350 miles I-90 until you reach the capital city of Ohio. 

One of Cleveland’s greatest attractions is its location on the banks of Lake Erie and the insane views that go hand-in-hand. Depending on the weather, you might want to go for a full day of water and lakefront activities or simply enjoy a waterfront stroll or dinner at one of the various restaurants located on the boardwalk. 

Cleveland has a full range of activities for the whole family to enjoy, so we strongly recommend planning for a couple of days here – you’ll soon see why it’s one of the best family vacation spots in the Midwest!

USA Chicago to New York - Cleveland - Lake Erie, Ohio 

The Rock and Roll Hall of Fame, the Great Lakes Science Center, the Cleveland Museum of Art, and the Cleveland Museum of Natural History are only a few examples of what Cleveland has on offer. 

The Children’s Museum of Cleveland, Ralphie’s actual house from A Christmas Story, complete with the Leg Lamp in the window, and the Cleveland Zoo will keep the little ones busy for hours, too, in case you’re travelling with kids. 

If you’re itching for a nature fix and have the time to indulge, Cuyahoga Valley National Park is a mere 20 minutes from the city. One of the best national parks on the east coast, here, you can hike the hills and forests while you look out for deer, beavers, and more than 250 bird species, including the iconic bald eagle! 


A 134-mile drive going southeast on I-80 will take you to your next stop: Pittsburgh, also known as Steel City. 

Famous for its steel production, fine architecture, and 446 bridges, this destination in Pennsylvania offers a plethora of things to do for kids and adults alike. You’ll need at least two days to really savor what the city has in store for you. 

USA Chicago to New York - Pittsburgh

Long gone are the days when the coal industry’s soot and grit defined the city. Today, Pittsburgh is a thriving arts and culture center, and a haven for nature lovers because of its privileged location on a plateau at the point where the Allegheny, Monongahela, and Ohio Rivers form a triangle. 

Besides a thriving gastronomical nightlife scene, Pittsburgh is home to marvelous attractions like the Phipps Conservatory and Botanical Garden, the Cathedral of Learning, a Gothic Revival skyscraper that towers above the University of Pittsburgh campus at 535 feet tall, and the Andy Warhol Museum. It is also the proud host of the world-renowned Carnegie museum, including the Museum of Natural History, the Carnegie Science Center, and the Carnegie Museum of Art.  

If you’re driving from Chicago to New York with the kids, few cities rival Pittsburgh when it comes to keeping them entertained. The Makeshop is an innovative studio where kids’ visions are converted into tangible objects. They’ll be fascinated with the collection of original antique vehicles, as well as the jungle gym and largest collection of items from Mister Rogers’ Neighborhood.

For those yearning for an amusement park, Kennywood is one of the oldest amusement parks in America, with six major roller coasters, water rides, a kiddie park, and classic rides. 

Lancaster, Pennsylvania 

Once you’re ready to leave the Steel City of Pittsburgh behind, you must take I-76 and head 238 east to Lancaster, home to the largest Amish settlement in the US and a great place to stop en route. 

A relatively short stop at this quaint village offers a unique opportunity to experience the vastly different way of life and rich history that traces its roots back to English, Dutch, and German settlers. 

USA Chicago to New York - Lancaster

Take the Amish Village tours for a peek at their rolling farmlands and farmhouses, schools, and outbuildings. Be sure to eat some hearty Amish food and shop for crafts made by the settlers who resist modernity and prefer an old-fashioned, simple way of life. 

Philadelphia, Pennsylvania

68 miles from Lancaster, going east on I-76, you’ll find Philadelphia, a stunning city full of historic landmarks and other highlights for the whole family. Again, our recommendation is to try to make it a two-day stop here so as to have enough time to explore the best sites. 

You simply can’t visit Philly without exploring the Historic District. After all, the area between Delaware River, 7th, Vine, and Lombard streets that span the original city boundaries is one of the key points where the US was born! 

USA Chicago to New York - Philadelphia

You’ll find several historic sites and iconic buildings here, including but not limited to Independence Hall – where the Declaration of Independence and the US Constitution were written  – and President’s House, the home of George Washington and John Adams during the 1700s when Philadelphia was the capital of the United States. 

Other must-see historical landmarks in Philly include the Museum of the American Revolution, Liberty Bells Center, the African American Museum, and the beloved Betsy Ross House. The latter is the picturesque house where Betsy crafted the first American flag, and you can wander through the small rooms and learn about her role in the American Independence. Family treasures include some original furniture, her eyeglasses, and her original Bible. 

Of course, not everything is history in Philadelphia. You can find other attractions, such as the Please-Touch Museum, Adventure Aquarium, Longwood Gardens, and the Drexel University Academy of Natural Sciences, all perfect for kids and families. The Franklin Institute, Sesame Place, and the Philadelphia Zoo are marvelous options for the little ones as well. 


Last but certainly not least on your road trip is New York City, which you’ll reach by taking I-95 and traveling northeast for about 95 miles. 

The most populous city on the US East Coast, NYC awaits you with all its hustle and bustle to cap off your road adventure with an exciting grand finale. The Big Apple is home to hundreds of attractions, including historic landmarks, museums, parks, and iconic neighborhoods, so do try to stay for several days if at all possible. 

USA Chicago to New York - New York City

New York City has many museums related to almost any theme you can imagine. They range from some of the most famous museums in the world that exhibit impressive collections to smaller premises that house small collections geared to all types of travelers, including art aficionados, fans of the quirky, engineers, or Instagrammers on the lookout for cool photo ops. 

The Metropolitan Museum of Art (Met), Museum of Modern Art (MoMA), National 9/11 Memorial Museum, and the American Museum of Natural History are a few of the not-to-be-missed iconic attractions, but you’ll find museums dedicated to gangsters, dogs, colors, skyscrapers, and much more. 

When the city bustle gets to be a bit overwhelming, you can “escape” to one of the many parks housed within the city limits. Central Park, of course, is the first one that comes to mind, being the oldest public park in the United States and one of the most iconic parks in the world.

Smaller green lungs in NYC worth checking out are Washington Square Park, the High Line, Battery, and Prospect Park – many of these parks make for great free activities with kids in NYC.

New York City is a tapestry of neighborhoods that fit together to form the marvelous metropolis that is the largest city in the US. We recommend trying to spend some time in some of the most iconic ones to get an ample idea of what the city is about. These include Soho, Greenwich Village, Washington Heights, Chelsea, DUMBO, and the famed Little Italy and Chinatown depicted in many films. 

Ready For a Chicago to New York Road Trip

Although the idea of this 12-hour drive may feel daunting at first, with many historic and scenic stops to make along the way, this is one of the best road trips in the USA for families.

We suggest you allow yourself 10 days to complete the journey, including time spent in both Chicago and New York City, to even touch on the highlights.

  • If you are not quite ready for an epic cross-country road trip with the kids yet, you can try one of these easier scenic drives in Illinois or a day trip from Chicago to get you used to hitting the road with littles in tow whilst still exploring beyond the Windy City!

Before You Go – Things to be Aware of Driving Chicago to New York City

  • You will be crossing time zones! Illinois is on CDT (CSDT), where as Indiana, Ohio, Pennsylvania and New York are on Eastern Standard Time (EST/ESST).
  • You’ll find road condition reports for Pennsylvania at 511pa.com and 511ny.org for New York state.
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