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This is a tough one. I understand what you are trying to accomplish, but it's not an easy trip. You used to be able to hop in a car in Chicago and take route 66 to LA/Santa Monica and find lots of small towns.
You could go to the UP of Michigan, but that isn't any different than traveling north from Vancouver.
I guess what I would recommend would be to start in Yellowstone National Park in Wyoming and travel East into South Dakota or Nebraska.
The other option is Northern Arizona to southern New Mexico. Lots of interesting scenery on that trip, and would be different from Canada.
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