First US Roadtrip! NYC - Cape Cod - Chicago and back for NYE

Hi, this is my first posting here so apologies for starting by asking for advice!

My partner and I are both English and we are spending the festive period in the states for the first time, and have arranged car hire. We arrive in New York on the 19th December, before collecting the car on the 22nd. We intend to drive to Cape Cod/Boston area until about the 26th/27th and then head west to Chicago to visit some friends for NYE. We then have to return the car on the 7th Jan in New York.

Our main concerns relate to the weather and how tricky driving might be (we have considered just using the car for the Cape Cod leg of the trip, and then flying to Chicago).

So, I guess my questions are:

1. What would be the best route to take west from Boston to Chicago, and what sights should we look out for on the way? Where should we stay? We are both quite interested in seeing the 'real' America, including some interesting small towns and finding good food. We also like areas of natural beauty but appreciate that some of these might be quite difficult to access at this time of year.

2. Similarly, what would be the best (and different) route to take from Chicago east to New York between approximately the 4th and 7th January?

3. Is the weather likely to make any of this impossible? Or are the main routes between big cities generally kept clear of snow?

Enormous thanks in advance for any help you can give us. We are so excited about seeing some of your country!

Matthew

The fastest and most efficient route from Boston to Chicago is I-90 all the way, but there are 2 downsides - it's a toll road for major portions, and there is a high potential for lake effect snow from upstate New York most of the way to Chicago. The Interstate highways are highest priority to be kept clear, but it can be daunting trying to drive them during a storm.