Hello from Muskoka Ontario. We did route 66 two winters ago. We left at the start of February, and went straight to St. Louis to begin. We wanted to get far enough south to get away from freezing, so we skipped Chicago. There are lots of info on YouTube on route 66. Justin Scarred has many, as well as Roamin Rich. I have lots on my YouTube channel, but im not a pro. I just do it for my kids to follow along. Heres one Cheers https://www.youtube.com/watch?v=qxXj4oemd_0