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Boston to Chicago drive

2 travelers   /   driving   /   3 days



Boston to Chicago road trip planner

Here's a sample itinerary for a drive from Boston to Chicago. If you're planning a road trip to Chicago, you can research locations to stop along the way. Find the best restaurants, hotels, and attractions based on the most talked about places recommended by Trippy members.

customize this trip

Day 1, 10:00 am:  start in Boston
drive for about 2 hours

Day 1, 11:52 am:  Northampton (Massachusetts)
stay for about 1 hour and leave at 12:52 pm
drive for about 3 hours

Day 1, 3:48 pm:  Cooperstown
stay for about 1 hour and leave at 4:48 pm
drive for about 2.5 hours

Day 1, 7:11 pm:  Newark (New York)
stay overnight and leave the next day around 10:00 am

day 1 driving ≈ 7 hours


Day 2, 10:00 am:  leave from Newark (New York)
drive for about 2 hours

Day 2, 12:05 pm:  Niagara Falls
stay for about 1 hour and leave at 1:05 pm
drive for about 3.5 hours

Day 2, 4:34 pm:  Cleveland
stay overnight at The Cleveland Hostel
leave the next day around 10:00 am

day 2 driving ≈ 5.5 hours


Day 3, 10:00 am:  leave from The Cleveland Hostel
drive for about 2 hours

Day 3, 11:46 am:  Toledo (Ohio)
stay for about 1 hour and leave at 12:46 pm
drive for about 2.5 hours

Day 3, 3:14 pm:  Mishawaka
stay for about 1 hour and leave at 4:14 pm
drive for about 2 hours

Day 3, 6:04 pm:  arrive in Chicago
eat at Lou Malnati's Pizzeria
stay at The James Chicago Hotel

day 3 driving ≈ 6 hours


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Enter a city to drive through on the way from Boston to Chicago.
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Where does my trip begin?

Your starting point is Boston, Massachusetts.

You can enter an exact street address if you want to get precise directions, but this is optional.




How many cars do we need?

Since there are only 2 travelers, we assume you're driving 1 car. You can adjust the number of people traveling at the top. We assume a maximum of 4 passengers per car, but you can change the number of cars to fit your situation.




Where should I stop along the way?

Northampton (Massachusetts)  (3 answers)
Cooperstown  (4 answers)
Newark (New York)  (3 mentions)
    questions about Newark (New York):
        Should we base ourselves in Newark or Rochester?
Niagara Falls  (52 answers)
    Niagara Falls  (18 mentions)
    Maid of the Mist  (5 mentions)
    Skylon Tower  (4 mentions)
    questions about Niagara Falls:
        best place
        Best free things to do in Niagara Falls?
        Best and most affordable hotel with bar and hot tub?
        Travel by car from Stowe to Niagara falls fastest route
        single person visiting Niagara Falls (US side)
Cleveland  (39 answers)
    Rock and Roll Hall of Fame and Museum  (13 mentions)
    The Cleveland Museum of Art  (12 mentions)
    Rock and Roll Hall of Fame and Museum  (6 mentions)
    West Side Market  (6 mentions)
    Great Lakes Brewing Company  (5 mentions)
    restaurants around Cleveland:
        Lola
        Lolita
        The Greenhouse Tavern
        Melt Bar & Grilled
        L'Albatros
    hotels around Cleveland:
        The Cleveland Hostel
    questions about Cleveland:
        Good restaurants for business dinner?
        What is your favorite restaurant in Cleveland?
        New to the city, friend coming to visit: What should we do?
        Vegetarian near Playhouse Square
        Best breweries in Cleveland?
Toledo (Ohio)  (6 answers)
    Toledo Zoo  (2 mentions)
Mishawaka




Where does my trip end?

Your final destination is Chicago, Illinois.

You can enter the exact street address of your destination, but this is optional.




Where's the best place to stay in Chicago?

Are you going straight to a hotel, or looking for a vacation rental or Airbnb?

The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in Chicago.

You can also see most people recommend as the best amount of time to visit. Find out how many days in Chicago to stay.

If you're looking for a quick answer, you can check out The James Chicago Hotel, which was mentioned 12 times on Trippy.

Here are some more hotels people talk about:

Hotel Palomar Chicago  (9 mentions)
Virgin Hotels Chicago  (8 mentions)
Thompson Chicago  (6 mentions)

Want to research more popular hotels in Chicago? Click the blue button below.






Where's the best place to eat in Chicago?

Need some recommendations on somewhere to get food?

Trippy members suggest Lou Malnati's Pizzeria, which was mentioned 36 times.

Here are some more restaurants people talk about:

Pequod's Pizza  (26 mentions)
Girl & the Goat  (24 mentions)
Big Star  (23 mentions)
Au Cheval  (17 mentions)

Want to research more popular restaurants in Chicago? Click the blue button below.






What are some things to do in Chicago?

This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.

These are some of the places people talk about on Trippy:

Millennium Park  (54 mentions)
Shedd Aquarium  (46 mentions)
Willis Tower  (38 mentions)
Lincoln Park Zoo  (35 mentions)

Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!

For example, here are some questions people have asked about Chicago. Click on any question to see answers from the community!

 Sunil Gupta from Mountain View asked:
Best Chicago pizza?  (18 answers)

 Katie Simons from Los Angeles asked:
What is your favorite restaurant in Chicago?  (15 answers)

 Blair Cabot from Halifax asked:
What to do in one weekend in Chicago?  (14 answers)

 지은 기 from asked:
airport transportation  (14 answers)

 Stacey Wall from Jackson, Mississippi asked:
What are the coolest hotels in downtown Chicago?  (12 answers)

Click the button below to explore more questions and answers related to Chicago.






Do I really have to go back home?

Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!

Want to plan the trip back? Get the reverse directions for a Chicago to Boston drive, or go to the main page to plan a new road trip.

You can also compare the travel time if you're flying or driving by calculating the distance from Boston to Chicago. Or get a full Boston to Chicago flight plan.

Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.

And if you know Boston well, please help your fellow travelers and answer their questions about Boston!






Return to top of page
At a Glance
without making any stops
total driving distance is 982 miles
driving time of 14 hours, 34 minutes
Chicago is 1 hour behind Boston
175 Boston travel answers
3 Northampton (Massachusetts) travel answers
4 Cooperstown travel answers
52 Niagara Falls travel answers
39 Cleveland travel answers
6 Toledo (Ohio) travel answers
1 Mishawaka travel answer
253 Chicago travel answers





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