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Chicago - West Coast X-country route

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So here is more or less the trip route I am planning for my Sept. 2016 trip in the Charger with my wife.

Are there any places along the route that are "must see" places?

It's not on the depicted route, but I was wondering if Flabob would be worth going out of my way to get to?

Based off local and seasonal conditions, will I be better off flying the route clockwise or counterclockwise?

Is anyone interested in joining the adventure?

Thanks!
Glenn

PS - The checkpoints shown on the map are not fuel stops... Just points for route planning at this time.

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