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Some people want to be completely flexible to take as much time as they like and then find a place to stay wherever they end up that night.
Others want to plan out a detailed itinerary and have their lodging booked well in advance.
Many people travel Route 66 in sections, doing a part one year and returning to drive another section the next.
To choose a particular section, you can read our Route 66 guide which includes recommendations and descriptions of several section of the route that are best suited to a number of interests and people.
There are advantages and disadvantages of both styles of travel, and most people end up traveling somewhere in between.
Knowing that you have some place to each night when you arrive in a town can make the trip a bit less stressful.
Use this Route 66 itinerary to plan your travels from Chicago to Santa Monica and get the most out of your Route 66 road trip.
Before you take off on your 2,400-mile “Mother Road” road trip, we’d recommend reading our Route 66 road trip planning guide to get you oriented with all the basics of driving Route 66.
Driving: If you have your own car, motorcycle, or RV and live in the U. (or maybe Canada) then driving may be the best option.
Most people do not have a full month to travel so we based our itinerary on the fact that 2 weeks is probably what would work for most travelers.
A big factor that should help you decide how long to drive Route 66 is to think about how much time you want to spend just driving each day.
For a Route 66 road trip, you’ll probably want to look for a car or RV rental company that allow you to rent a vehicle at one end of your journey (e.g., Chicago) and return it at the other (e.g., Los Angeles).
Car Rentals: There are a lot of major rental car companies (Thrifty, Hertz, Alamo, Avis, Dollar, Enterprise, etc.) that have offices in both Chicago and Los Angeles and allow one-way rentals so check around and compare prices.