I learned from my first motorcycle trip on Route 66 that the unoffical starting place is at Lou Mitchell's Restaurant on E. Jackson Blvd (oneway street east). They have been there forever. From there drive east to Michigan Ave, turn left, then left again onto Adams St. (oneway street west) There is a Route 66 sign there that says: BEGIN HISTORIC ROUTE 66. On Jackson Blvd. just before Michigan Ave there is a Route 66 Sigh that says: END HISTORIC ROUTE 66. I took pictures of both of them on our ride. I have been telling everyone to get the Route 66 Guide Books from the magazine. They will have you going the right way on your journey.
I will be returning to Chicago this summer to repeat the journey. I have been studying the guide books almost every night so I won't miss too much this time.