Boston to Chicago road trip: Best stops, distance & drive time

The best road trip stops on the Boston to Chicago drive are Niagara Falls, Cleveland and South Bend. The distance from Boston to Chicago by car is 1,009 miles, with a 16h4m driving time.

Planning a Boston to Chicago road trip itinerary

The Boston to Chicago drive connects two of America’s great cities on the way from Massachusetts to Illinois.

Boston is drenched in history, with the Boston Tea Party Ships and Museum a good first stop on the revolutionary trail. Other Boston attractions include the New England Aquarium, the View Boston observation deck and the Fenway Park baseball stadium.

There are also hundreds of Boston tour options, some more distinctive than others. Good choices include walking the Freedom Trail with a historian guide and story-packed tours of the Harvard campus. For a more Italian flavour, try a North End pizza and history tour. On a sunny day, try a sightseeing day sail around Boston Harbor.

If looking for the best Boston accommodation options, pick the Langham for luxury or the Lenox for a slice of cool in the Back Bay neighborhood. The Liberty, meanwhile, is a jaw-dropping conversion of a former prison.

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.

Book mobile-friendly tickets here.

Boston to Chicago distance and driving time

By car, the distance from Boston to Chicago is 1,009 miles. That makes for a driving time of around 16 hours and four minutes. The quickest route is along the I-90.

The best stops to add to a Boston to Chicago road trip itinerary are Niagara Falls, Cleveland and South Bend.

Best stops between Boston and Chicago: Niagara Falls

There are two cities called Niagara Falls, one either side of the infamous waterfall. The city of Niagara Falls, Canada, offers much more for tourists, and is something of a mini-Vegas. You’re better off crossing the border and choosing from a vast array of experiences in Niagara Falls, Canada.

However, for the purposes of this guide, we’ll assume you’re staying in the United States. Things to do in Niagara Falls, New York include the Maid of the Mist boat ride to the base of the falls, a Cave of the Winds highlights package tour and a mobsters tour full of stories that takes in the illuminated falls after dark.

Boston to Chicago road trip attractions: 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.

Boston 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.

Skyscrapers around the Chicago River in Chicago. Photo by David Whitley/ Best3Stops.

More Boston road trips

More Chicago road trips

Boston to Chicago road trip: Best stops, distance & drive time

Planning a Boston to Chicago road trip itinerary

Our favourite thing to do in Chicago

Boston to Chicago distance and driving time

Best stops between Boston and Chicago: Niagara Falls

Boston to Chicago road trip attractions: Cleveland, Ohio

Boston to Chicago drive: South Bend, Indiana

More Boston road trips

More Chicago road trips

Popular US road trips

Road trips from US cities

Archives

Categories

Contact Best3Stops