We are going on a road trip next summer. We are flying to either NYC or Boston (we have been in both cities before and are not spending any time there). We have to stop in Toronto, and would really like to stop in Chicago. We like to travel in a way that means new places and hotels every night (except two nights in chicago and maybe one other place..), and 2-5 hours driving each day. The children are 2 and 5 years.
Any tips for itinerary from the two different locations? Should we end in Chicago or other suggestions (total driving time for the trip around 30-40 hours..)?