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Last Minute Drive from PA to Oregon, Please Help with Travel Plans

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My son is relocating in early August to Portland, OR and I am driving with him from PA and then flying back. We have about 12 or 13 days to get to Portland and then I will spend about 2 or 3 days in Portland before flying home. Right now we are planning to drive to Chicago, spend one or two nights there, drive to Minneapolis, spend one night (he has a friend there), drive through the Badlands to Black Hills, spend one or two nights in Black Hills/Mt. Rushmore. Then we plan to drive to Yellowstone and Grand Tetons, spend about 2-3 days there and also hope to hit Jackson Hole. We have a place to stay in Alpine if we choose to stay there. After that we will drive through Idaho, Craters of the Moon and Boise, and then go to Portland. We have a tent, I also have points for staying in Starwood and Marriott hotels. I would appreciate suggestions for other places we should plan to see, whether or not this is a doable itinerary, suggestions on places to stay, and whether we should plan to enter Yellowstone from the North or Grand Tetons and then Yellowstone from the south. Any other information would be greatly appreciated. Thank you!

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