My friend and I are planning a month-long road trip this December. We intend to purchase/hire a car in LA (which is a better idea?) and start our trip there. The destinations that we definitely want to go to are Chicago, New York, Toronto and Montreal. At the end we will probably get a flight back to LA and go home from there. Any feedback, ideas, advice about the trip would be much appreciated! How will it be driving in winter? How long will we be able to spend in each place keeping in mind we have a month altogether? Are there any stops along the way we should go to?