Re: route 66 cross country road trip--anyone ever done this?
Can you stream Netflix? If yes look in documentaries; there is a fairly recent six-part doc that you should watch called Billy Connolly's Route 66. If you are not familiar with him, Billy is a legendary comedian and this documentary follows him as he takes the entire trip from Chicago to LA. It might help you decide if this is the trip for you and, if so, what you might want to see along the way.