East Coast Road Trip - Dec/Jan

We would like to visit quite a few east coast cities on the East Coast leg of our US Trip at the end of the year...
We would like to visit: Chicago, New York, Washington DC, Boston and Niagara Falls.
I would love some advice on planning an itinerary... we will fly in to somewhere, then hire a car and drive to the other cities, over a 1-2 week period.
I was also wondering what the roads are like between these areas - I am a little concerned about planning a road trip during snow season, so I would love some advice in this area.

Thank you for your help! :)

Welcome to the RoadTrip America Forum!

You could fly into any one of Chicago, New York, Washington DC, or Boston and start a loop from there. Two weeks will give you ample time for this trip; one week would probably be too much like work. If you fly into Chicago, head East to Niagara, then South to Washington, DC, and then up to New York City and Boston, you are looking at around 1600 miles total, but you can get from each point to the next in a single day's trip.

If you do a round trip, heading back to Chicago, that adds another 1000 miles.

Although you are likely to find snow in any one of those areas, the most likely area to be significantly affected by snowfall would be in the Niagara Falls area. The lake effect snow in that portion of New York state is a major factor. Alas, nobody can predict the weather this far ahead of time. For all we know, it could be an unusually mild winter this year. That said, the only weather situation likely to shut down these cities would be a major blizzard, and even then, the road crews in these areas tend to be right on top of things and are able to get the roads cleared in short order.

My advice in this situation would be to stick to the Interstates if there is any potential for harsh weather conditions.