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Driving from Chicago to Boston in December?

Chicago, Illinois
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Driving from Chicago to Boston in December?

Hi, forum friends!

I am making a relatively last-minute move from Chicago to Boston and am debating if it's better to pay movers to haul my stuff or enjoy an impromptu road trip in the process :) I have never done this drive and I'll have a full rented truck, a boyfriend, and a cat to keep my company. We would prefer to drive ourselves and stop along the way.

My concerns are:

Hills! The topographical map shows quite a bit of elevation - at least from this flatlander's perspective. The route is all highway, but even those sometimes get tight and twisty - can anyone comment on whether that's a valid concern? (Keep in mind - driving an unfamiliar truck).

Weather! The shortest route hugs the great lakes, which would be beautiful, but I'm concerned about snow and ice - again in an unfamiliar truck.

Robbers! We would ideally want to make our stopover in a place with covered parking to avoid any funny business with our truck full of stuff. Is there a reasonable halfway point in a big enough city that this might be a realistic expectation? (We'd book ahead of time).

I have a tendency to over-focus on what could go wrong so I wanted to put the question to the experts. Is it worth it to brave the open road in the middle of winter on that particular route?

Thanks so much for any insight and advice!!! :)


Marina, California
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for Tucson
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1. Re: Driving from Chicago to Boston in December?

Hills shouldn't be a concern. They're pretty minor. Most of what you'll see is around Syracuse, coming in and out of the Hudson Valley, and then the Berkshires in Western Mass. Definitely not mountains though, so not a big deal. If you stick the Thruways and pay your tolls, then you'll have the best chance of avoiding both snow/ice and curvy roads.

Snow is always a concern. That region got a few inches this week already. They're used to it though. It has to be an enormous, catastrophic storm to stop traffic on the interstates around the Great Lakes.

If you're worried about security when stopping, then don't stop for the night. This drive can be done in one very, very long day, so just plan on doing that. You have two drivers, after all. If you want to stop, then do so in a smaller town, especially in the Rust Belt. Looks like the midway would be about Dunkirk, NY, which is nice because that's where the NYS Thruway starts. For security, it's best to pick a motel that allows you to pull next to the room, or has security patrolling the parking lot. Nothing's certain though, of course, and the former type of motel is often older and less desirable.

I'm impressed you were able to rent both a boyfriend and a cat on such short notice...

2. Re: Driving from Chicago to Boston in December?

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