We’ve driven the entirety of Route 66, and we’ve already put together a detailed guide to planning a Route 66 trip and guide to all the best places to stay on Route 66. Spanning over 2,400 miles from Chicago to Los Angeles, this driving route will take you through a broad span of America, from big cities through to vast desert landscapes. If you’re looking to take a road trip in the USA, perhaps the most iconic of all is Route 66.