A panoramic view of night-lit and skyscrapers of Chicago with Buckingham fountain in Grant Park at the front
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Road Trip From Boston To Chicago

Updated by Dianne Titos on February 21 2024

A road trip from Boston to Chicago is not a small endeavor. You'll be spending a lot of time on the road, going across several states before reaching your destination. The length of this trip might discourage a lot of people from doing it by car, but driving from Boston to Chicago will be a rewarding experience that you won't forget.

The 980-mile road trip from Boston to Chicago will take at least 15 hours of driving across Massachusetts, upstate New York, Ohio and Indiana. Take a few days to explore National Parks and towns on Lakes Erie and Michigan or detour via Niagara Falls.

If you're thinking of taking this herculean journey, read on for everything you need to know before setting out, as well as some ideas for stops and places to see.

How far is Boston to Chicago and how long will the road trip take?

There are a few different routes you can take to get from Boston to Chicago, and all of them will take at least 15 hours on the road. You'll need to add on a few hours for bathroom breaks, meal breaks, and fueling up.

The route itself is about 983 miles long, going through several states, and finishing in a different time zone. In theory, if you were very committed to taking this entire trip in a day, you could. But you'd have to skip every sight you're passing, and you'd be on a very tight schedule.

Also keep in mind that traffic will delay you, and if you leave Boston during rush hour or on a Friday or Saturday, you'll have a harder time getting out of the city. This will be true for the other cities you pass through, so make sure you allow for any traffic delays in your schedule.

Because the route is so long and it's hard to predict delays, it's best to split it into 3 or 4 days. This way, you can drive more leisurely, and take your time checking out the parks and cities you're going to be driving past. You'll be glad you skipped out on the stress of trying to complete a 15-hour road trip in a day and allowed yourself to enjoy the journey.

An aerial view of green forest-like trees and Lakeside road along Lake Erie Coastline in a good weather
Driving along the coastline of Lake Erie on the way to Chicago from Boston makes for amazing views.

Whether you're flying into Boston or you simply don't have a vehicle in the city, renting a car for your road trip is something you'll want to take care of ASAP.

For an easy-to-compare view of rental options for your road trip from Boston to Chicago, take a look at our partner site, RentalCars.com.

Best road trip route from Boston to Chicago

No matter what route you take, you'll be passing through the States of Massachusetts, New York, Ohio, and Indiana before reaching Chicago. The best route will take you along the shores of Lake Erie, allowing you to stop at Niagara Falls before continuing along past Cleveland towards Chicago.

You'll be passing plenty of cities where you can stop to recharge and explore before you get to Chicago.

Road trip route from Boston to Chicago

Despite the length of the road trip from Boston to Chicago, this is a straightforward route. Leave Boston via the I-90, following this highway across Massachusetts until you reach the Hudson River in New York State. From there, take exit 22-61 to merge onto the I-87.

Follow the I-87 until you reach Albany, and then merge back onto the I-90. Continue through Cleveland, following the I-90 the rest of the way across Ohio and northern Indiana before finally reaching Chicago.

Best places to stop between Boston and Chicago

This is going to be a long trip, so here are a few places you might want to stop in along the way where you can stretch your legs and spend the night.

Stop in Syracuse, New York

Syracuse, nestled in the heart of New York State, is a city rich in history and culture, offering a delightful mix of urban life and natural beauty. Known for its vibrant university community, impressive architecture, and lush parks, Syracuse invites travelers to explore its unique charm.

Just a short drive from the city center, the Hampton Inn & Suites Syracuse North Airport Area is a comfortable and convenient option. Despite its close proximity to the highway and the airport, guests are pleasantly surprised by the quiet and peaceful ambiance inside the hotel.

Each morning, guests are welcomed with a complimentary hot breakfast, perfect for fueling a day of exploration. For those on the go, the Hampton On the Run® Breakfast Bag, available Monday through Friday, provides a convenient and tasty option. Should you arrive late or need a snack, the 24-hour Suite Shop convenience store is always open.

The hotel's indoor pool and fitness center provide excellent opportunities for relaxation and maintaining your fitness routine. The decor throughout the hotel is homely, clean, and modern, ensuring a comfortable and welcoming atmosphere.

Syracuse's attractions are easily accessible from the hotel. Destiny Mall, one of the largest shopping centers in the region, offers a variety of shopping, dining, and entertainment options. The natural beauty of Onondaga Lake Park is just a 7-minute drive away, perfect for a leisurely stroll or a picnic by the lake.

Explore Cleveland, Ohio

Since you're driving through Cleveland anyway, why not make it a stop on your road trip? Consider booking a room at the Ritz-Carlton, where you'll enjoy an on-site fitness center and restaurant at this classy hotel.

From the Ritz-Carlton, it will only be a short trip to Cleveland's Rock and Roll Hall of Fame. Make sure to take some time to visit the Cleveland Museum of Art, as well as the West Side Market when you start getting hungry.

The skyline of Cleveland with Key Bank, Rock and Roll Hall of Fame, and Science Center Building in a cloudy blue sky morning
Cleveland is a great place to stop and break up the road trip from Boston to Chicago.
Ami Parikh/Shutterstock.com

Remember to visit the Cleveland Museum of Natural History, and spend a few hours touring Cleveland's historic Little Italy.

Spend some time in Toledo, Ohio

Toledo, Ohio, known for its rich industrial history and vibrant arts scene, is a charming city perched on the shores of Lake Erie. As you explore Toledo, you'll discover a diverse array of attractions, from renowned museums and historic theaters to scenic parks along the Maumee River. The city's welcoming atmosphere and cultural richness make it an ideal destination for travelers.

In the heart of this lively cityscape, Homewood Suites by Hilton Toledo Downtown offers a serene and comfortable retreat. The hotel boasts fantastic views of the city, with some rooms offering a mesmerizing overlook of the water, providing a picturesque backdrop to your stay.

Guests can enjoy the luxury of space in the hotel's spacious suites, many of which include seating areas, perfect for relaxing after a day of exploration. The inclusion of kitchenettes in each suite caters to those who prefer a more self-sufficient stay, giving you the flexibility to cook and dine at your leisure.

Situated just 300 meters from Fifth Third Field, the hotel is an ideal base for baseball enthusiasts looking to catch a game. For those interested in the performing arts, the Valentine Theatre, a historic venue hosting a range of performances, is a mere 700 meters away.

Things to see on a road trip from Boston to Chicago

Since this is such a long trip, it's hard to make a complete list of things to stop and see. There are definitely some places you should make a point of trying to stop at, though.

  1. The Amazing World of Dr. Seuss Museum: This museum is located in Springfield, Massachusetts which was the birthplace of the infamous Dr. Seuss. Spend the day in his hometown reliving an element of your childhood.
  2. October Mountain State Forest: This 16,500-acre forest is the biggest state forest in Massachusetts. Stop at the October Mountain State Forest to take a break from city life and spend some time in nature.
  3. Albany: There are so many things to do in Albany, New York. Check out the performing arts center The Egg, get some shopping done, and visit the Albany Institute of History and Art.
  4. Montezuma National Wildlife Refuge: Located close to Syracuse, the Montezuma National Wildlife Refuge is a breeding ground for migratory birds, and includes 6 bald eagle nests. Three of the eagles in the refuge have been in the park since 1987.
  5. Mendon Ponds Park: Visit the several beautiful locations in this park, like the Devil's Bathtub. This park is home to a peat moss bog that features a floating island and several carnivorous plants.
  6. Rochester: Spend some time in this New York State city exploring its zoo and several museums, including the George Eastman Museum and the National Susan B. Anthony Museum and House.
  7. Buffalo: The second-largest city in New York, Buffalo is home to several historical sites like Frank Lloyd Wright's Martin House, a naval and military park, and the Albright-Knox Art Gallery.
  8. Niagara Falls: This could be another trip all on its own! As you reach Buffalo, New York, go ahead and take a detour up north to check out these incredible falls. Pack your passport so that you can see the attractions on the other side of the US/Canadian border and cut through to Detroit on your way.
  9. Oak Openings Preserve Metropark: Just outside of Toledo, you'll find the Oak Openings Preserve Metropark. This is the largest of Toledo Area's metroparks. Here you'll find picturesque sand dunes, as well as several rare species of plants.
  10. South Bend: Stop by this this city and check out the Grotto of Our Lady of Lourdes at the University of Notre Dame. This site is a reproduction of the grotto of the same name located in Lourdes, France.
  11. Indiana Dunes National Park: You'll find this beautiful park along the shores of Lake Michigan. Enjoy some time bird-watching, hiking through the forests, or enjoying the beach.
The green trees reflected the water with the leaves falling near a green kayak along the Calumet River in Indiana Dunes National Park.
Go kayaking along the Little Calumet River near Indiana Dunes National Park.

Best time to go on a road trip from Boston to Chicago

If you're planning on taking this journey, it will be best to avoid going during the winter. From November to March, you'll have to deal with snow and low temperatures as you drive. Ice and snow can make the roads unsafe, and many of the parks you might want to check out will be closed.

On the other hand, going in the summer will mean a lot of crowds. You'll have to contend with other tourists if you want to visit the Art Institute of Chicago, Grant Park, or the Field Museum. This is true for any of the other cities you're planning on stopping in.

But if you can handle the crowds, you'll have the opportunity to experience peak festival season in Chicago. From blues to jazz to gospel music, if you're a music buff summer is a great time to check out Chicago. There are plenty of beer and food festivals too to satiate your taste buds.

Just know that if you do decide to go in the summer, crowds will be plenty, plus the temperatures can reach up to 84°F.

If you want to experience the festive atmosphere of Chicago while having to cope with fewer crowds, going during one of the shoulder seasons might be best. If you go between April and May in the spring, you'll catch the beginnings of festival season, along with milder weather and a far lower number of fellow tourists.

September and October are also good months to visit. The temperatures should still be fairly warm, you won't have to deal with many crowds, and you'll still catch the tail end of the festival season.