Two weeks, six weeks, eight weeks, a year

David - Thanks for stopping by and posting. We did our trip from Chicago to Santa Monica in 8 days. I know some people out there are aghast that we moved along so quickly, but we're young and not necessarily drowning in vacation time and/or money, so we worked with what we had. I feel like we still saw nearly everything we wanted to see, so if 8 days is all you can manage, it will not be a waste of your time.

If I had to do it again, though, I wouldn't do it in any less than two weeks. I think my parents are looking at taking a month to six weeks (this would certainly allow you to do many side trips to attractions that are slightly off the Route).

One thing that did catch me off guard - because we're Midwesterners, we planned longer days across Illinois and Missouri, figuring "Eh, we've seen Illinois and Missouri a million times!" But there seemed to be a lot more Route 66 attractions along the first several hundred miles of the Route than you might find in, say, New Mexico. Just something to keep in mind.

I hope you'll stop back and let us know how your plans are going!