Created using the major cities along The Legendary Route 66 One of the original U.S. highways, US Highway 66, ran from Chicago, Illinois, all the way to Los Angeles, CA covering over 2,400 miles. It has been the inspiration for a hit song as well as a hit TV show. Route 66 will forever be symbolic with the Rock & Roll side of Pop Culture. To add our little bit of magic to this iconic sign we took the major cities along the route and re-created the famous Route 66 sign.