Weather will be a big factor that late in the year. Mid November after last year would make me worry.
What exactly are you looking for? Urban exploration, restaurants ect? Or natural wonders.
I any case you may want to head south or south west for better weather prospects. A 36 ft fiver will exclude most national park cg and a lot of other federal cg with the exception of COE sites.
I'm not sure if you are aware of this but most people hold the speed down to 60 mph or so when towing. Higher speeds can lead to bad surprises. Blown tires if nothing else.
An 800 mile day will make the next day, even if you don't travel less than pleasant. Off hand I don't know of a lot of places to visit within 600-800 miles of Chicago. We strictly prefer natural sites our self and avoid cities. So I would push a couple of 400+ mile days in to get to more interesting areas.
Just an off the cuff suggestion, Big Bend would be good that time of year followed by Southern New Mexico and Arizona. However Big Bend is 1400 miles. If the weather cooperates southern Colorado may work. But Grand Sand Dunes is 1100 miles. Followed by Mesa Verde and the UT parks. Zion BTW is 1800 miles.
Arctic Fox 25Y Travel Trailer
2018 RAM 2500 6.7L 4WD shortbed
Straightline dual cam hitch
400W Solar with Victron controller
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