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One of the oldest routes in America, and immortalised by Nat King Cole, Route 66 is undoubtedly an iconic road trip adventure.

But of course, with a distance of almost 4000 KM, spanning from Chicago to LA, it’s best to know what you’re letting yourself in for.

And that’s exactly what this guide is for!

Read on to find out more about how to get your kicks on Route 66!

Planning Tips For Route 66: Things You Need to Know Before Getting Your Kicks

Plan Time for Roadside Attractions

Arizona Post Office Route 66 RF

With Route 66 cutting a line horizontally across North America, it spans many states, and has become famous for its many roadside attractions. With plenty to see and do along the way, it’s important to build in time for sightseeing.

After the Great Depression and World War II, the highway was used to reach the sunny coast of California which signified the demographic shift from East to West. More than 210,000 people migrated to California to escape the despair that had hit the West, and Route 66 symbolized the “road to opportunity”, and a renewed spirit of optimism.

Roadside attractions began to pop up, and the route became known as “The Main Street of America”, linking remote and under-populated communities with two of the most thriving 20th century cities – Chicago and Los Angeles.

While it was later decommissioned as a Highway, there’s a whole industry that has sprung up around this route, for tourists who want to experience the history. And most of these are kooky, kitschy, roadside attractions.

There’s the world’s second-largest rocking chair in Fanning Missouri, as well as the wild burros that walk the streets in Oatman, Arizona. And there’s the somewhat comical Whale of Catoosa in Oklahoma.

There’s Texas’ Cadillac Ranch where ten Cadillac’s have been driven nose down into the dirt and spray painted by local graffiti artists with vibrant colors. Check this post for more iconic attractions.

Choosing the Right Vehicle

Car drive road trip RF

There’s nothing wrong with flying into the States and booking an average car rental; in fact, this is what most travelers do. Though just be aware that there are other options too.

Being that this is a legendary old road, a popular option is to hire a classic American muscle car like a Mustang, to really embrace the feeling of old school Americana.

Or, you could go for a convertible for the experience of driving cross country with the top down, along a long and open road.

Many people too opt for a two-wheeled adventure, and if you have your bike license, why not think about leasing a Harley? You can complete all or just part of the route.

Where Should You Start Your Journey?

Route 66 RF

A critical element of your route 66 journey is deciding where you’ll begin. If you want to do the entire route, you’ll fly into Chicago and start at the sign located at 78-98 E Adams St.

Travellers from outside of the country will usually fly into O’Hare International Airport, while those catching a domestic flight can choose from a selection of hubs including Chicago Midway airport and Chicago Rockford airport.

That said, this is a mammoth route, which joins up with many other highways and roads in many other States, so you don’t have to start in Chicago, you can choose to drive just a part of the route if limited by timing and costs. Here is a list of the 10 best major cities on Route 66.

Of course, travel documentation you’ll need for entering the USA includes a valid passport and an ESTA visa. And if you’re planning on driving, make sure you have your drivers license on you at all times.

A foreign drivers license is valid in 49 US states, except for Georgia, which requires an additional license for foreigners, known as an International Driving Permit (IDP).

Where Should You Stay?

RV Campervan RF car drive road

When planning out your budget, it’s important to remember that travelling along Route 66 is not a quick trip. In fact, the fastest that the whole route can be done is a little over 2 weeks, with most visitors taking around a month.

As such accommodation will be your biggest expense (though you can of course opt to just drive a section instead of the whole thing).

One of the most straightforward and economical options is to stay in motels along the route. In fact, during off-season you can often rock up without a booking (October to April, though keep in mind that many facilities close down during this time, being that it’s off-peak).

Many people completing the whole route go for the campervan option. Traveling in an RV means you can stop and camp for the night without needing to find a hotel or motel. And there are plenty of RV parks and free camp sites along the route.

You can of course mix and match, free camping some nights, other in cheap motels, and then splurge in iconic cities on a nice hotel. Don’t miss out on unique accommodation along the route either; one fabulous example of this is the teepee campsite in Holbrook, Arizona, which is decidedly retro.

After you’ve planned and booked your trip, make sure you read up on some of the history of Route 66. Understanding its history and significance will allow for a deeper, more immersive experience.

Megan is an Australian Journalist and award-winning travel writer who has been blogging since 2007. Her husband Mike is the American naturalist and wildlife photographer behind Waking Up Wild; an online magazine dedicated to opening your eyes to the wonders of the wild & natural world.

Having visited 50+ countries across all seven continents, Megan’s travels focus on cultural immersion, authentic discovery and incredible journeys. She has a strong passion for ecotourism, and aims to promote responsible travel experiences.


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