A road trip from Boston to Chicago is no small thing. You will spend a lot of time on the road and cross several states before you reach your destination. The length of this trip can discourage many people from driving, but a trip from Boston to Chicago will be a useful experience that you won’t forget.

The 980 mile journey from Boston to Chicago takes at least 15 hours and passes through Massachusetts, the upper reaches of New York, Ohio and Indiana. Spend a few days exploring the national parks and towns of Lake Erie and Lake Michigan or make a detour to see Niagara Falls.

If you are planning this ducal journey, read everything you need to know before you leave, along with some ideas for a stopover and observation point.

What is the distance between Boston and Chicago and how long is the journey?

There are several routes from Boston to Chicago, all taking at least 15 hours to get there. For toilet breaks, lunch breaks and gas stations, add a few hours.

The route itself stretches about 983 miles across several states and ends in a different time zone. Theoretically, you could do it if you were very interested in making the whole trip in one day. But you’ll have to miss all the shows where you’re going and you’ll have a very busy schedule.

Also remember that traffic will slow you down and if you leave Boston during rush hour or on Friday or Saturday, it will be harder to get out of the city. This also applies to other cities you pass, so make sure you take delays in your planning into account.

Since the journey is very long and the delays are difficult to predict, it is best to divide it by 3 or 4 days. This way you can drive more quietly and take the time to see the parks and cities you pass. You will be happy to escape the stress of a 15 hour journey in one day and enjoy the trip.

On a clear day, with a bird's eye view of green wooded trees and the Lakeside Highway along Lake Erie
On the road from Boston to Chicago along the coast of Lake Erie, the view is breathtaking.


Best route from Boston to Chicago

Whichever route you take, you will pass through Massachusetts, New York, Ohio and Indiana before reaching Chicago. The best route is along the shores of Lake Erie. So you can stop at Niagara Falls and continue through Cleveland on your way to Chicago.

You’ll pass through many cities where you can stop to recharge and explore before arriving in Chicago.

Transport route Boston to Chicago

Despite the length of the journey from Boston to Chicago it is a direct route. Leave Boston on the I-90 and take this highway through Massachusetts to the Hudson River in the state of New York. From there, drop off at exit 22-61 to connect to the I-87.

Follow the I-87 to Albany and then take the I-90 again. Continue through Cleveland and follow the I-90 through Ohio and northern Indiana before reaching Chicago.

Best stopover between Boston and Chicago

The journey will be long, so there are several places where you can stop along the way, stretch your legs and spend the night.

Stop in Syracuse, New York

They’re going through Syracuse anyway, so why don’t we do it sometime? Stop by the New York State Fair and visit Clinton Square in Syracuse for an overview of the city’s history.

You can enjoy a performance in the Sightseeing Theatre or visit the Eriekanaal Museum. If you want to go shopping, you will find a large shopping center in Syracuse with Destiny USA.

If you plan to spend the night in Syracuse, ask about the Syracuse inner harbour. The hotel has a bar, restaurant, indoor pool and fitness centre. It is close to many of the sights of Syracuse. You’re only 0.6 miles from US Destiny and 0.8 miles from Clinton Square. It will also be a short trip to the Rosamond Gifford Zoo.

Explorer Cleveland, Ohio

Since you’re still passing through Cleveland, why don’t you stop along the way? Consider booking a room at the Ritz-Carlton Hotel, where you can enjoy the fitness centre and restaurant of this elegant hotel.

From the Ritz-Carlton it’s only a short drive to the Cleveland Rock and Roll Hall of Fame. Don’t forget to visit the Cleveland Museum of Art and the West Side Market if you’re hungry.

Cleveland Horizon with Key Bank, Rock and Roll Hall of Fame and Science Center under a cloudy blue sky in the morning
Cleveland is a great place to stop and take a break on a trip from Boston to Chicago.

Girlfriend Parikh/Shutterstock.com

Don’t forget to visit the Natural History Museum of Cleveland and spend a few hours in the historic Little Italy in Cleveland.

Spend some time in Toledo, Ohio

Toledo is situated on the shore of Lake Erie and has a zoo, museums and parks. Book a room at the Renaissance Toledo Downtown, which is just a 10-minute drive from the Toledo Zoo. This beautiful hotel overlooks the city center, and if you plan to take your dog on this trip, don’t worry – this hotel is suitable for pets.

If you’re in town, check out the Toledo Art Museum in the old West End. This museum consists of 45 galleries and an enormous collection of artifacts. There is also the Glass Pavilion, where you can learn about the history of glass production in the city.

Don’t forget to spend some time in Toledo’s Botanical Garden, which contains 50 acres of beautiful flowers.

Visit to a road trip from Boston to Chicago

The journey is so long that it is difficult to make a complete list of what you can stop and see. There are some places that are worth stopping.

  1. The amazing world of the Dr. Seuss Museum: This museum is located in Springfield, Massachusetts, the birthplace of the infamous Dr. Seuss. Spend the day in his hometown and experience the element of your childhood.
  2. Oktyabrsky State Mountain Forest: This 16,500 hectare forest is the largest state forest in Massachusetts. Stay in the Oktyabrsky Mountains State Forest to take a break from city life and spend some time in nature.
  3. Albania: There’s so much to do in Albany, New York. Visit the Egg Performing Arts Centre, browse the shops and visit the Albany Institute of History and Art.
  4. Montezuma National Park: Montesuma National Park, near Syracuse, is a breeding ground for migratory birds and includes 6 Bald Eagle nests. Three eagles from the shelter have been in the park since 1987.
  5. Mendon Park ponds: Visit some beautiful places in this park, such as the Devil’s Pool. In this park there is a swamp with a floating island and several carnivorous plants.
  6. Rochester: Spend some time in this New York State city and explore the zoo and several museums, including the George Eastman Museum and the Susan B. Anthony and House National Museum.
  7. Buffalo: Buffalo, New York’s second-largest city, is home to several historic sites, including Frank Lloyd Wright’s Martin House, a naval and army park, and the Albright-Knox Art Gallery.
  8. Niagara falls: This could be another trip in itself! When you arrive in Buffalo, New York, make a detour north to see these incredible waterfalls. Get your passport ready to visit the sights across the Canadian border and travel to Detroit on the way.
  9. Oak openings receive Metro Park: Just behind Toledo are the oak holes of the Metropolitan Park Reserve. It’s the largest metro park in Toledo. Here you will find picturesque sand dunes and several rare plant species.
  10. Southern elbow: Stay in this city and visit the Notre-Dame de Lourdes Cave at Notre-Dame University. This website is a reproduction of the cave of the same name in Lourdes, France.
  11. Indiana Dunes National Park: You will find this beautiful park on the shores of Lake Michigan. Enjoy your holiday by birding, walking in the forest or enjoying the beach.

The green trees reflected the water, the leaves fell next to a green kayak along the Kalumet River in Indiana Dune National Park.
Kayaking on the Little Calumet River at Indiana Dune National Park.


Best time for a drive from Boston to Chicago

If you’re planning this trip, it’s best not to drive in winter. From November to March you will have to deal with snow and low temperatures during the trip. Ice and snow can make the roads unsafe, and many parks you want to see will be closed.

On the other hand, there will be a lot of people driving in the summer. You will have to compete with other tourists if you want to visit the Art Institute of Chicago, Grant Park or the Field Museum. This applies to any other city you want to visit.

But if you get along with the audience, you’ll get the chance to experience the highlight of the festival season in Chicago. From blues to jazz to gospel, if you’re a music lover, summer is a great time to explore Chicago. There are also many beer and food festivals to satisfy your taste buds.

If you decide to travel in the summer, be aware that there will be a lot of people and that the temperature can reach up to 84°F.

If you want to feel Chicago’s festive atmosphere and get along with fewer people at the same time, it’s best to choose one of the off-seasons. If you travel in spring, from April to May, you will see the beginning of the festival season, milder weather and a much smaller number of other tourists.

September and October are also good months to visit. The air temperature should still be warm enough, you don’t have to face the crowd and at the end of the festival season you still have your tail between your legs.

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