16 Mar 2016
It is traditionally travelled from east to west, i.e. from Chicago to Los Angeles. Chicago is where it all begins, on the shores of Lake Michigan,from the shadow of some of highest skyscrapers of the continent. From the top of the John Hancock Center, you can enjoy the most spectacular view of the Windy City's skyline, from the safety of a fully glazed, 360° observatory. There is the ol' Route 66 that comes a little south then turns up toward Chicago, or there's the 15-70-76-80 that goes through Las Vegas, below Salt Lake, through Denver, up through Nebraska and on to Chicago.
In most cases, especially in less populated areas, Interstate highways adopted a similar approach and thus follow Route 66 all the time to this journey. That is a lot of driving with basically no time at your stops when you drive. You would need 5-6 days in Yellowstone alone to begin to feel like you saw what you wanted to see. Your route to Yellowstone and Mount Rushmore takes you out of the way. Instead you should pick a park or two on your route and spend a full day or two in those parks instead of going as far north as Yellowstone and Mt Rushmore.
There are no tolls for crossing states and we can easily can do this trip without using toll roads once out of Chicago. Don't need to use tollroads in Oklahoma. Bridges into San Francisco are toll and via Golden Gate cashless. Toll roads in LA easily can be avoided. Same for Denver. The continuation of the route through Colorado is wonderful (I'd skip Rocky Mountain NP in favor of a more southern route through Colorado - Telluride/Ouray to Gunnison to maybe Leadville and then Denver). It's so nice try to spend a night in one of the mountain towns along the way, and put the pedal to the metal after hitting the plains.
After nearly 2,500 miles, Route 66 comes to an end before the world-famous panel of Santa Monica Pier at the platform of the chic little town of Santa Monica, a suburb of Los Angeles on the Pacific Ocean shore.