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Portland to Chicago in mid October

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Hi everyone,

I'm considering a roadtrip from Portland to Chicago, starting around 6th or 7th of October.

My main concern being the weather, can anyone advise me if this is a good choice ?

and then :

- what 's must see in terms of landscape (I'm a photographer).
Badlands and Yellowstone are ok in mid october ?

- how long should I plan for this trip ?
Thanks a lot for any help you could provide with this....

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