Sorry - I've been a pest lately............ One of our considerations for a fall trip is to start in Illinois & meander along Route 66. I like to meander, but also am not willing to risk being 'hotel-less' due to fall travel so I would like to plan ahead a bit (of our 7 night trip last year the hotels we were at were sold out 5 out of the 7 nights and they were turning people away when we were checking in). We have taken numerous trips to St Louis over the years and a few down as far as Springfield & Branson, but those have pretty much been on the 4 lanes. We have hit a few 'well known' 66 landmarks such as Ted Drewes numerous times & I have been to Cozy Dog in Springfield, although husband hasn't. I'm thinking 4 days down with possibly 2 days back (not as much stopping on return of course). We will be starting in Western Wisconsin so we are a good 5 hours to a start point of Joliet or so (likely would not start in Chicago). Just curious if anyone has done a road trip like this, what your favorite stops were, how long you spent doing it, did you stay at more 'classic motels' (if there are any left) or just stick with the known chains at the interstate, etc. I have been looking at the site for drivingroute66 - but would like personal opinions from anyone here. Thanks!!