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I did this in 1999, and it is about 1700 miles. It took me and a friend, driving a moving van and my car, three days to make the trip. We stopped in Western Montana and Eastern South Dakota. We didn't make any time for site seeing and drove about 8 hours a day. If you wanted to burn the candle at both ends, you could make it in two days. Warning: Eastern Montana is BORING.

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Q: How many days does it take to drive to Oregon from Chicago?
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