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.
We’d recommend that you don’t spend more than 4 to 5 hours per day driving in your car.
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.
If you have 8 to 10 days, you might want to come up with an itinerary that has you doing sections of Route 66 between Chicago and Los Angeles, and use the Interstate the rest of the time to get from place to place.
But a better way if you are short on time would be to just choose to explore a section of Route 66 based on your interests and explore that section at a more leisurely pace.
Certainly we’d recommend doing some research before your trip, and if there are any special places you want to stay or special things you want to attend (e.g., a concert or baseball game for instance), I’d book those in advance.
We recommend at least 2 weeks, although the more time you have the better. But most travelers time is dictated by the amount of vacation time they have and when they can travel.
Be sure to check to see if there are any extra add-on fees for one-way rentals before you book.
We usually find that Enterprise have the best rates for one way rentals.
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.