So, how much time do you have and what do you want to see.
I can think of 3 directions: Chicago, Detroit, Toronto, Quebec City....
2. Chicago, Cleveland, NYC and north. deadly IMHO too much interstate, too little scenery
3. Chicago, west up-along Wisconsin, Michigan UP, Sault Ste. Marie, across to near Ottawa and down various way to the province of Quebec. Then you can go other ways, like near the south Shore of the St. Lawrence via NB, NS, PEI to NL, or on the north Shore of the St. Lawrence up through Labrador and across
Now, my fav way would be the longest and most Canadian way, ie #3 and variations. On my cross continent trip I crossed the big river to The Saguenay and then across to Ontario and stayed on Rte 11 going. Returning I took Rte 17 and the Trans Canada (with Manitoulin thrown in). Of course, I have worked in ON and with people in all those places on my northern route.
I have a truck camper, so boondocking is easy. Mostly, I prefer more rural areas because I have two dogs. It takes longer to find rural boondocking places. Parking lots for churches, etc. can be easier. Some provinces you can park near a hospital. Or there is the eatery parking lot.....
Enjoy
:B
