I wanted to drive through Canada and the US. What is a good itinerary? I want to visit some cool cities in the States including New York. Would it make sense to stop in Chicago too? What are the roads like in September? I'd like to book my hotels in advance so I'm trying to come up with a set itinerary. I don't want to drive more than 1000kms a day. Any help with this question would be appreciated! Thanks.