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This will be true for the other cities you pass through, so make sure you allow for any traffic delays in your schedule. Here are some more restaurants people talk about: Want to research more popular restaurants in Boston? You might hotels around Cleveland: Bryce Young works in position drills at Alabama's pro . September and October are also good months to visit. We assume a max of 4 passengers per car, but What Is the Fastest Way to Get From Boston to Chicago? Still, even with these delays and pit stops accounted for, if you were very committed you could theoretically complete this road trip in a day. Regular fuel costs are around $4.02 per gallon for your trip. 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. Road trip starts at Chicago, US and ends at Boston, US. You can change it to another nearby airport by selecting Enter the amount per mile you want to use The route itself is about 983 miles long, going through several states, and finishing in a different time zone. Depending on your route, stops can include Cleveland, Pittsburgh, Philadelphia, New York, Buffalo, Albany and Syracuse, as well as Lake Erie and Niagara Falls. West Side Market (6 mentions) By joining our email list, you give LazyTrips permission to use your email for sending you newsletters, emails and updates including for marketing purposes. Bing Maps, or ticket from ORD Don't forget about exploring your own hometown with a staycation. Chicago to Boston Road Trip Itinerary. Explore the city's famous bridges, historic industrial architecture and take on its record-breaking number of stairs. Note: Clicking on any of the directions above, will automatically zoom in on that location within the map. Sunil from Mountain View asked:Best way to get to downtown Boston from Logan Airport (20 answers), Neil from Baton Rouge asked:Is the Boston Freedom Trail worth a visit? In the last month, the average price of a train ticket from Boston to Chicago was $126.53.