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Trip from Toronto back to Vancouver Island through the USA

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Hi folks,
Returning home from a family wedding in Toronto. We are driving through Canada to Toronto, and I have that organized. But I wanted to see what your opinions /ideas are about our trip home.
Day 1..Oct 2, Wednesday : Toronto to Chicago (Bypass city , so will stay by the hwy somewhere).
Day 2: Chicago to Fairmont, Min
Day 3: Fairmont to Rapid City...See Mt Rushmore,Crazy Horse, Sturgis either that afternoon or next morning.
Day 4: Rapid City to Billings
Day 5:Saturday Oct 6: Billings to West Yellowstone through Beartooth Pass...booked at Kellys
Day 6: West Yellowstone Kellys
Day 7: West Yellowstone to Jackson...seeing GTNP
Day 8:Jackson to Missoula
Day 9: Missoula to Spokane...tour around
Day 19: Spokane to Pt Angeles and take the late ferry to Victoria, then up island home.

We plan to stay on Hwy 90 most of the way. My husband is in a wheel chair, so hiking won't be in the picture, but we'd like to drive as much of the parks as we can and see as much as time permits. Will pack our lunch in the parks as suggested in forums.
We normally stay at hotels that have breakfast included, for ease of morning routines.
Thinking of the Super 8 in Jackson...any info on accommodation...Motel 6 would be too small I think.
Is this schedule doable?
Wondering if day 6 will be too long..Billings-W Yellowstone?
I'd appreciate any info, and ideas from the group!

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