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Route 66 Self-Drive Holidays

Route 66 Self-Drive Holidays

Get your kicks on Route 66 as you travel from Chicago through the heart of continental America to Los Angeles. Iconic and nostalgic, follow America’s beloved ‘Mother Road’ on a memorable Route 66 road trip of spectacular scenery, quirky landmarks and quintessential cuisine.

Stretching 2,448 miles, crossing eight states and three time zones, Route 66 was one of the original US highways and played an integral role as the main route for migrants travelling west to California during the Dust Bowl of the 1930s. With se...

Stretching 2,448 miles, crossing eight states and three time zones, Route 66 was one of the original US highways and played an integral role as the main route for migrants travelling west to California during the Dust Bowl of the 1930s. With sections of the road now protected and numerous hotels, diners and attractions along Route 66 preserved, experience the culture and diversity of this great nation on an epic cross-country Route 66 road trip itinerary of a lifetime. Journey from the plains of the Midwest, through farmland, desert and mountain passing famed Route 66 landmarks along the way to the sun-kissed Californian coast.

This is your chance to live the great American dream as you capture the culture and diversity of this great nation. Take it at your own pace with a self-drive tour, discovering the many vibrant cities along Route 66 on this epic cross-country road trip of a lifetime.

Booking with Pettitts Travel
1

Getting to know you
A crucial part of our process, discuss your plans with us either by phone, video or in person.

2

Helping you to design your trip
Entirely tailor-made, there is complete flexibility to incorporate all your requirements.

3

On-hand support, when you need it
Our team are on hand to answer any questions and ensure you are fully ready, and excited, for your trip.

4

Full confidence whilst you are away
Enjoy full support from our UK team and trusted local partners throughout your journey.

We’re pleased to confirm that Pettitts Travel will not apply any surcharges to our package holidays when we are operating as a tour operator, regardless of changes in global costs. The price you agree at the time of booking is the price you will pay, a commitment we have proudly upheld for the past 38 years.

Start planning your Route 66 trip with our Travel Consultants

  • Experts in tailor-made holidays
  • Honest pricing with no hidden extras
  • ABTA and ATOL protected
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The experience of a lifetime

BF - Route 66 - May 2025

I have just got home from travelling Route 66 and what an adventure it was! I enjoyed every minute of it and I’m so glad that I included some 'off Route 66' experiences, such as the Grand Canyon and Monument Valley. I covered 1,573 miles in total, and none of the journeys were excessive. All the flight, hotel and car rental arrangements worked out perfectly.

All told, it was THE experience of a lifetime, and a wonderful celebration of my 70th birthday.

Many thanks Astra for all your help and advice, plus that of your colleagues, in organising my trip. Don’t be surprised if (when!) I’m in touch again in the not too distant future…

Your Route 66 Holiday

Each Route 66 itinerary we arrange is unique and can be tailored to your exact needs and wants. As one of the greatest road trips in the world, we recommend hiring a car and driving overland at your own pace, exploring the fabulous cities and experiencing iconic attractions along the way. Our travel experts can offer advice on all aspects of your Route 66 road trip from car hire and accommodation to the best things to see and do.

One of the most common questions we are asked is ‘how long does it take to drive Route 66’? The entire route between Chicago and Los Angeles can be completed in a little over two weeks but, for those with less time, the journey can be shortened by starting in Oklahoma City. Alternatively, if you wish to stay longer, extend your holi...

Each Route 66 itinerary we arrange is unique and can be tailored to your exact needs and wants. As one of the greatest road trips in the world, we recommend hiring a car and driving overland at your own pace, exploring the fabulous cities and experiencing iconic attractions along the way. Our travel experts can offer advice on all aspects of your Route 66 road trip from car hire and accommodation to the best things to see and do.

One of the most common questions we are asked is ‘how long does it take to drive Route 66’? The entire route between Chicago and Los Angeles can be completed in a little over two weeks but, for those with less time, the journey can be shortened by starting in Oklahoma City. Alternatively, if you wish to stay longer, extend your holiday by following coastal Highway 1 to beautiful San Francisco or incorporating the spectacular Grand Canyon or dazzling Las Vegas. Although these are not part of the classic Route 66, many people like to incorporate these iconic stops whilst they are in America.

Things to see and do on Route 66

Each Route 66 itinerary we arrange is unique and can be tailored to your exact needs and wants. As one of the greatest road trips in the world, we recommend hiring a car and driving overland at your own pace, exploring the fabulous cities and experiencing iconic attractions along the way. Our travel experts can offer advice on all aspects of your Route 66 road trip from car hire and accommodation to the best things to see and do.

One of the most common questions we are asked is ‘how long does it take to drive Route 66’? The entire route between Chicago and Los Angeles can be completed in a little over two weeks but, for those with less time, the journey can be shortened by starting in Oklahoma City. Alternatively, if you wish to stay longer, extend your holi...

Each Route 66 itinerary we arrange is unique and can be tailored to your exact needs and wants. As one of the greatest road trips in the world, we recommend hiring a car and driving overland at your own pace, exploring the fabulous cities and experiencing iconic attractions along the way. Our travel experts can offer advice on all aspects of your Route 66 road trip from car hire and accommodation to the best things to see and do.

One of the most common questions we are asked is ‘how long does it take to drive Route 66’? The entire route between Chicago and Los Angeles can be completed in a little over two weeks but, for those with less time, the journey can be shortened by starting in Oklahoma City. Alternatively, if you wish to stay longer, extend your holiday by following coastal Highway 1 to beautiful San Francisco or incorporating the spectacular Grand Canyon or dazzling Las Vegas. Although these are not part of the classic Route 66, many people like to incorporate these iconic stops whilst they are in America.

Gas pump in Arizona, USA
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Speak to a Route 66 Specialist

When is the best time to drive Route 66?

A trip along Route 66 can be taken at any time of the year but heavy snowstorms and icy roads can severely interrupt travel plans during the winter months. Also bear in mind that during early spring and late autumn, some attractions will be closed or only open for reduced hours. May to October is the optimal time to drive Route 66, with May, June, September and October being our preferred travel months. July and August are extremely popular months to travel but do bear in mind that the western states experience extremely high temperatures.

How long does a Route 66 road trip take?

As long as you want it to! Remember, the joy of the Route 66 experience is the journey itself, not the destination. We recommend you allow at least 14 days to travel from Chicago to LA if you want to sample a true taste of Route 66 and its many attractions, plus a few more days if you’re planning to add the Grand Canyon and Las Vegas to your trip.

What type of accommodation will I be staying in on Route 66?

Accommodation along Route 66 is extremely varied, from luxurious and boutique city hotels to quirky motels and charming lodges. You will also find a wide range of international hotel chains to choose from. Be prepared that outside of the big cities, accommodation choices can be limited and more basic, but there are always comfortable and characterful places to choose from and we can advise at the time of booking. At Pettitts Travel, we tailor-make your Route 66 itinerary and can offer hand-picked accommodation suggestions to suit you.

Can I book a convertible car to drive Route 66?

There are an extremely limited number of convertible vehicles available to rent in Chicago and many car hire companies will not permit trans-state rentals. Convertibles are also not particularly practical. It is possible however to experience part of the journey in a convertible between Las Vegas and Los Angeles. A standard car or even an SUV can be arranged from Chicago to Las Vegas or similar, then a convertible can be collected for the rest of the journey across to Santa Monica.

Do I have to pay a one-way fee on my car hire?

Depending which car hire company you choose and which route you drive, you may or may not have to pay a one-way car hire fee. One of our experienced Travel Consultants can discuss your options with you during the planning stage.

Is it cheaper to travel Route 66 in a motorhome?

The simple answer is no. Motorhome rentals charge for mileage packages and when covering a distance as great as Route 66 (over 2,400 miles), this can work out at almost $1000 or so. Add to this the vehicle hire charge, campsite fees for each overnight stop, the fuel required for the journey and a hefty one-way drop-off fee, it is far more cost-effective to rent a car and stay in hotels and motels along Route 66. It is also quite difficult to find and pre-book campsites to stay in along the route.

Are there plenty of places to refuel on Route 66?

You will find gas stations at least every 30 miles or so along the majority of Route 66 and the surrounding roads. In more remote areas such as Arizona, there are fewer gas stations so be certain to fill up as often as possible and avoid the fuel gauge dropping below the halfway mark. If you are heading out to the Grand Canyon on a side trip, it is worth refueling in Kingman to avoid paying premium prices in the desert area. Fuel is usually paid for before filling up at most gas stations in the USA.

How to plan a Route 66 road trip?

Our Route 66 travel experts will be delighted to offer advice on all aspects of a Route 66 road trip from car hire and accommodation to the best things to see and do. So, whether you wish to drive the entire route between Chicago and Los Angeles, shorten your journey by starting in Oklahoma City or incorporate one of the country’s other iconic sites such as the Grand Canyon or Las Vegas, we will be delighted to help you plan your perfect holiday. Contact us via our website or by calling 01892 515966.

Book with confidence with Pettitts Travel

We are here to take the stress out of your holiday, to provide you with impartial well-informed advice and assist you in navigating regulations and guidelines to ensure your trip goes as planned.
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