NYC to Chicago road trip: Best stops, distance & drive time
The best road trip stops on the New York City to Chicago drive are Penn’s Cave, Cleveland and South Bend. The distance from NYC to Chicago by car is 794 miles, with a 12 hour driving time.
Planning a New York City to Chicago road trip itinerary
The New York City to Chicago drive connects New York to Illinois, travelling between two of the greatest cities in the US.
Highlights of New York City include the Empire State Building, the 9/11 Memorial Museum, the Museum of Modern Art and the American Museum of Natural History.
For great New York tours, try the boat trip to the Statue of Liberty and Ellis Island, a night time city lights helicopter flight and a Greenwich village food tour.
More unusual options include catacombs tours, a round-Manhattan architecture cruise and a guided exploration of Grand Central Station’s secrets.
You seriously need to shop around to find affordable New York City accommodation. Start looking for deals here.
Chicago’s skyscrapers, music scene and massive collection of cultural attractions make it arguably the most exciting city in the US to visit.
Highly recommended Chicago experiences include an architecture river cruise, a gangsters and ghosts tour of famous Mob sites and a bike tour of the lakefront neighbourhoods. It’s also worth paying a visit to the Field Museum, the 360 Chicago observation deck at the Hancock Tower and the Chicago Architecture Center.
Recommended Chicago hotels include the Club Quarters Central Loop for astonishingly good value. Also consider the Intercontinental Chicago Magnificent Mile for its amazing, historic pool, and the entertainingly science-themed Hotel EMC2.
Our favourite thing to do in Chicago
The Chicago architecture cruise has a phenomenal wow factor, with the boat gliding between some of the world’s most legendary skyscrapers.
We found the commentary matches the views, too. Expect a fascinating run-down of the city’s history – and plenty of surprising detail about the buildings you’re seeing.
New York City to Chicago distance and driving time
By car, the distance from New York City to Chicago is 794 miles. That makes for a driving time of around 12 hours. The quickest route is via the I-80 and I-90.
The best stops to add to a New York City to Chicago road trip itinerary are Penn’s Cave, Cleveland and South Bend.
NYC to Chicago road trip attractions: Penn’s Cave
Penn’s Cave in Centre Hall PA makes for an unusual cave tour, as it’s mostly done by boat. After heading down 48 steps to the boat dock, the cruise through the cave system shows off extraordinary stalagmites and stalactites before drifting along an underground lake.
Outside the cave complex, there’s a wildlife park and maze. You can also try your hand at gem panning.
Best stops between New York City and Chicago: Cleveland, Ohio
There are many strong attractions in Cleveland, including the Cleveland History Center. But the big stand out is the Rock N Roll Hall of Fame. It’s an extremely reverent trawl through rock ‘n roll history, looking at the origins and development of the genre. There’s a massive amount of memorabilia, with sections devoted to several Hall of Fame inductees.
The Rock N Roll Hall of Fame is dense, detailed and capable of sucking up the best part of a day.
Alternatively, Cleveland tour options focus on neighbourhood food scenes, the city’s best craft breweries and Downtown’s public art.
New York City to Chicago drive: South Bend, Indiana
South Bend is one of those towns that’s just fun to hang out in. It’s a university city, and the student life gives it the bulk of its energy. Notre Dame University tours take in the campus and key buildings such as the hugely impressive Basilica of Notre Dame.
For car-lovers, however, the key attraction in South Bend is the Studebaker National Museum. Studebaker Cars were made here until 1963. The museum tells their story and has plenty of classics on display.
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