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Route 66 is the ultimate American road trip and we’ve put together a comprehensive 2 week Route 66 itinerary to help drivers navigate this historic route.This detailed day-by-day Route 66 itinerary covers all the basic details (mileage, general route) and sightseeing highlights along the 2,400 mile route.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.
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.
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.
We cover quirky Route 66 roadside attractions, historical buildings, vintage roadside diners, museums, natural wonders, and so much more.
We also provide suggestions for where to eat and where to stay each day along the drive with a strong focus on Route 66 era businesses.