Don't drive the "top states" as you put in late in the year. Some years ago, I drove from the East Coast back to my home in Western Washington, the extreme northwest of the US. I left in early November. I had all the time I wanted, so I was in no rush, but it was the most terrifying trip of my life. Chicago was icy cold, with a bit of snow, but the trip descended into nightmare in South Dakota, when I encountered a blizzard like something out of Little House on the Prairie. I was able to take shelter, fortunately, but as I left the next day, I was treated to the sight of car after car after car lying in the highway median after spinning out. Crossing the Rockies in Montana and Wyoming and the Cascades in Washington was horrifying. The roads were very steep and icy.

Go at least a month earlier. Chicago is great but not in November. The wind comes right off Lake Michigan.

Also, why do you want a huge vehicle? Although gas is cheaper here than in the UK or Europe, it is still expensive enough to warrant choosing a smaller car. If you want to visit cities, it is much easier to park in a reasonably sized vehicle than in a humongomobile.

Where are you interested in going in Canada and why? It's a magnificent country, of course, but if you are trying to visit multiple US states you will have a lot on your plate as it is.

Should you be interested in changing the route you've described, the Chesapeake Bay Bridge in Virginia is beautiful and impressive. You mentioned your interest in bridges, and I think you would love to see it. The region is interesting, too.

hi

google maps has a way to save 10 layers with 10 destinations each but it is not a good tool for the planning part. it is best used to look at the overall plan. I use a spreadsheet which is where i save the 10 destinations. Even with only 10 destination you can drag the blue line to make it go where you want it to go rather then get google suggested routes.

For renting any vehicle i have seen where you have to turn it in every so often and get a new one but to avoid one way car hires best to look at doing loops when one way rentals might apply. The Ford Expedition is in the same category of those mentioned. BUT have a look at the Chrysler Pacifica as an option - the top of the line version is a luxury model with lots of room. (yes it is a minivan but not one of old)

For driving into Canada you need to have the insurance paperwork and then you have to make sure that you can get unlimited miles (kms) as some may only have that options for a few neighbouring provinces or even neighbouring states.

We drove Boston to San Diego this past summer and the easiest part of the planning was knowing that cold weather and snow and ice was not going to have to enter the formula. We discussed 4 different routes, including I-90 across the northern states, and ended up taking a more middle route, that included parts of Colorado that I don't think you should consider at your time of year.

If you can do this from May to September, your possibilities are endless

Hi

Definitely start earlier in the year.

What is on your bucket list?

I think 300-350 miles per day is a lot, even with an occasional layover day. Have you done long road trips in the past? Does this travel style work for you?

We'd call them the "northern" states, just like you have referenced the southern states.

Note that "PCH" refers to a short section of the coast road just north of Los Angeles. It does not refer to Hwy 101 in Oregon nor refer to Hwy 1 in California. But I think the coastal route is what you mean (and what you may not be thrilled driving in the stormy early winter.)

Southern states best done in spring, fall or winter as summer is hot and humid.

Southern states known for history, music, great food, lush scenery and friendly people.

Southern states best spots to visit imo are New Orleans, gulf coast beaches, Great Smoky mountains and cities of Savannah and Charleston with Southern culture and food. For musicthe cities of Nashville and Memphis.

Bing maps allows more than 10 entries.

https://www.bing.com/maps/

You don't need a car in Chicago. We had 4 nights in Chicago without a car years ago.

This is not a good idea IMO.

Bad idea on the humongomobile unless you need seats for 7 or 8 people.

Bad idea to do it in November and December.

No reason to be in Chicago for Thanksgiving. It’s a family holiday where folks go home to be with their extended family and eat traditional foods. Thanksgiving in Chicago is not really a “thing” like Christmas in NYC. New England would be more Thanksgiving territory like Plimoth Patuxet where the Pligrims landed in Plymouth Massachusetts if you wanted to go somewhere special.

Can you come another time of year?

I'm with panchopup. Forget the huge gas hog SUV. It will be big and cumbersome in cities anyway. I really don't understand your time of year choice. I'd head south of the Mason Dixon and enjoy some good temps. Savannah is my favorite Southern city. The mountains in NC definitely should be a priority as well. That Bay Bridge Tunnel complex as mentioned is fantastic. Continue south to Kitty Hawk and the birthplace of aviation. South being the key word here.

https://www.cbbt.com/