This guide will take you on a tour of the most interesting locations of Route 66 in the US. We have researched and gathered all the information needed so you can see this amazing route with your own eyes.

I have always been fascinated by Route 66. When I was a kid, car trips like this one were part of the plan; there was most likely not a lot of money in our pockets and back then it was illegal to stunt behind the wheel. My dad used to talk about the trip he took through Colorado, which ended up being the farthest he ever went out of state.

From Chicago to Los Angeles, the historic highway taken by early 20th century travelers stays true to its Midwest roots as it winds across the heartland, a drive that feels as much all-American as down-home.

Vacation. I’ll be honest with you, it usually sounds great in theory. The promise of all the glory and wonder a new destination can offer the traveler makes even the shadiest of motels seem glamorous. But let me spare you some pain, in my experience, vacation is rarely all that great. Who wants to travel halfway across the country for vacation when you’re still going to have to do chores like pay bills and take care of your animals? And who wants to wonder if their pets will have food when you’re gone? It’s not a huge stretch to say that for most vacations it’s more about getting away on your own than having a grand time.

Vacation On Route 66

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.

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.

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! 

Things to Know Before you Take Off on your Route 66 Drive

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.

Our planning guide covers the history and current status of the historical route, tips on how to stay on the route, tips on figuring out how much time you need to drive Route 66, a list of some of the highlights, packing tips, and a list of resources.

Our itinerary has suggested stops for each night, but we also have a dedicated guide to classic Route 66 hotels and motels if you are looking for places to stay.

Below is some basic information about how to get to Route 66, where to rent a car for the drive, and how to figure out how long it will take you to drive Route 66. 

Getting to and from Route 66

The first thing to think about in planning your Route 66 road trip is how you are going to get to the starting point of Route 66 and how you are going to get from the Route 66 ending point back home. 

Driving

 If you have your own car, motorcycle, or RV and live in the U.S. (or maybe Canada) then driving may be the best option. However, if you live far from the starting or ending point (e.g., Florida, Maine, Nova Scotia) then it might make more sense to fly there and rent a car. If you do drive your own car, just remember you have to also drive the 2,000+ miles back.

Flights

 If you are planning to begin and end your Route 66 experience with flights, I’d recommend flying into one of Chicago’s 2 major airports (O’ Hare or Midway) and then flying out of either Los Angeles International Airport (LAX) or Long Beach Airport (LGB).

Trains

 If you are planning to begin and end your Route 66 experience by train, Amtrak has a number of trains to and from both Chicago and Los Angeles from a number of destinations around the country.

Buses

The main national bus company in the United States is Greyhound and you can get to or from Chicago and Los Angeles from just about anywhere in the country (as well as some parts of Canada and Mexico). It just may take some time!

There are a few other bus carriers that run parts of this route and you can search, compare, and book bus tickets on Busbud.

Route 66 Car Rentals

If you are renting a car, motorcycle, or RV, you’ll likely want to book a one-way rental unless you are able to drive it back. For a Route 66 road trip, you’ll probably want to look for a car or RV rental company that allows 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 we suggest using a service like Rentalcars.com to check around and compare prices.

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 has the best rates for one way rentals.

Motorcycle Rentals

Those looking for a motorcycle rental for Route 66 might check out Eagle Rider and Ride Free. Both are able to do one-way rentals.

RV, Motor Home, & Campervan Rentals

For RV rentals, there are several companies that allow one-way rentals with offices in both Chicago and Los Angeles which include El Monte RV and Cruise America. 

We recommend using Motorhome Republic to check on RV rental prices as they can compare prices across the major RV rental firms in the USA for the dates you want to do the trip. You can book your RV for the USA through them here. 

If you are planning a round-trip journey (e.g., pickup and return to Chicago) then you might also want to compare the prices of traditional rental agencies with those of peer-to-peer RV companies such as Outdoorsy, RVshare and RVEzy.

Should I Plan my Route 66 road trip in advance? 

It is entirely up to you how much you want to plan ahead. 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.

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 sleep each night when you arrive in a town can make the trip a bit less stressful.

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.