The Mother Road, and its sites and stops, is disappearing at a fast rate. The published guide books are good, and recommended. However, as you enter a new state, stop at a known Rt66 stop, and get the latest local publication on RT66. it will be more current (by a suprisingly long shot). When we went, some of the well known sites dropped off literally weeks or days before we got there.
If starting at the Chi-Town end, be careful as you are coming into Kansas. The Mother Road will actually deposit you in a farmer's heavy equipment barn. :rofl. Apparently, some of the road's property has been sold to private parties and used for something else, so you have to go as far as you can, then orienteer yourself to the next place it picks up, where you can cruise it. The eastern end of Rt66 is a serious orienteering task. Fun, but not an efficient putt. From western Kansas on west, the interstate just got laid over the top of Rt66, and gets straight. I hate interstates. East of there, in Kansas, Rt66 weaves from one side of the interstate to the other (essentially serving as the local access road on the sides of the interstate), and sometimes vectors far enough off that you lose the interstate all together, and get to enjoy the ka-thump-ka-thump-ka-thump of the original rt66 concrete road. You'll know it when you see, hear, and feel it. Also, it will be noticeable in that it has gently curved curbs on either side.
Do it. You'll enjoy it. Just don't be in a hurry.
Enjoy,
Rich P