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Route 66 Road Trip

Image of a Route 66 Highway sign in Santa Monica - KILROY
View the full itinerary as a list

Recommended duration

3 weeks


Start in Chicago, end in Los Angeles

Travel type

Road trip


Flights, car rental and surf camp

Book this itinerary
Stretching nearly 4,000km from Grant Park in Chicago to Santa Monica Boulevard in Los Angeles, through three time zones and eight states, Route 66 is the ultimate American road trip. Experience everything the States is known for, from cities that never sleep to prairies that roll for miles.

Start in the Windy City of Chicago before spending three weeks travelling through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California, finishing with a week of surf lessons at Dana Point. Along the way, catch a game or two of American football, eat your fill of corn dogs, explore a Cadillac ranch and have your breath taken away at the Grand Canyon.

We've included car rental in this itinerary, but you can change it to a campervan if you'd like - up to you! It's also good to mention that when you're renting a car abroad, make sure to have your travel insurance in order. Don't have one yet? No worries - we can help you out with that. 

*Price is a 'from' price per person based on two people over 25 travelling together. Reach out to us if you're younger - it's not a problem!

What's included:
  • Return flights to the USA from the UK (arrive Chicago, depart Los Angeles)
  • 2 nights' accommodation in Chicago
  • 21 days of car rental (Hertz FCAR model)
  • 7-day surf camp at Dana Point in California
  • 3 nights' accommodation in Los Angeles
  • Booking fees
  • Your own travel specialist
What's not included:
  • Travel insurance (but we can help you with that)
  • One way fee of USD $500 + local tax
  • Vaccinations
  • Meals
  • Accommodation between Chicago and Los Angeles (but we can help you with that too)
  • Optional activities

Road trip suggestion Route 66

Home - Chicago - Springfield - Kansas City - St Louis - Joplin - Oklahoma City - Amarillo - Santa Fe - Gallup - Grand Canyon - Las Vegas - Los Angeles - Home

Route 66 officially starts in Chicago and ends in Los Angeles, but you can also flip the route around and go from LA to Chicago instead. This will save you the one-way car rental fee, as many companies end up with too many cars in LA and not enough in Chicago. So let us know your preference and we'll arrange the itinerary to suit you.

Chicago, Illinois

Your epic Route 66 starts in Chicago with two nights of accommodation to give you time to explore the city and pick up your vehicle.

While you're here, don't miss a basketball game with the Chicago Bulls. And make sure you visit one of the city's many retro blues bars before packing the rental car and starting your road trip on "The Mother Road".

Kansas City, Missouri

Next we recommend that you take a little detour and stop by Kansas City. Visit the iconic Power and Light district and experience everything this place has to offer: bars, live music, food and shops. You could also take yourself to watch either American football or baseball while you're here. It's easy to get tickets and you're guaranteed a great show and atmosphere.

Springfield, Illinois

Springfield is your first iconic Route 66 stop. The city is Abraham Lincoln's hometown and you can get a sneak peek into his first home at the Lincoln Home National Historic Site. Springfield is also the birthplace of American corn dogs and drive-thru restaurants, so it's a great place to sample America's fast food.

St. Louis, Missouri

Next stop is the city of St. Louis where you can try delicious ice cream at the Ted Drewes parlour. While you're here you can also walk along the Mississippi River and take a selfie in front of the huge Gateway Arch.

Joplin, Missouri

Joplin is a city rich in Route 66 history. You can visit landmarks like the Route 66 Mural Park and the Boots Motel, which has been restored to its original 1940s charm. Make the most of your car rental and visit the Grand Falls, known as the largest continuously flowing waterfall in Missouri. It's a beautiful natural attraction located just a few miles southwest of Joplin and a great spot for picnicking, hiking, and photography.

Oklahoma City, Oklahoma

In Oklahoma you'll likely meet other Route 66 enthusiasts from around the world, especially at the Route 66 Vintage Iron Motorcycle Museum and the National Cowboy & Western Heritage Museum. Make sure to also check out Bricktown, a picturesque district with old warehouses now operating as restaurants, bars and shops.

Amarillo, Texas

Howdy y'all! Everything is bigger in America and that goes for Texas, too. Test your stomach at the Big Texan Steak Ranch – if you can eat a 2kg steak in less than an hour, you get it for free. If you want an authentic cowboy experience, go to the Amarillo Livestock Auction where you can meet real cowboys.

Santa Fe, New Mexico

On the journey from Amarillo to Santa Fe you'll pass the strange attraction known as the ‘Cadillac Ranch’ where 10 classic Cadillacs are half buried in the ground.

Your trip takes you to the historic city of Santa Fe, one of the oldest cities in the United States. Remember to take time to relax in one of New Mexico's many hot springs.

Gallup, New Mexico

It's time to learn about Native American culture and history in New Mexico. One third of the inhabitants of Gallup are of Indian descent. Local Indian guides can show you around the beautiful ruins of "Sky City" in Acoma, a native American reservation.

Grand Canyon, Arizona

With its stunning and unique landscape, the Grand Canyon is a true natural wonder. The surroundings are beautiful, and the place also contains an exciting cultural history. It is definitely worth driving the distance from Flagstaff to get here!

Las Vegas, Nevada

Before ending your road trip in LA, make a stop in Las Vegas. Aim to arrive when it's already dark outside, so that you get to experience the whole spectacle of the neon lights while driving down the I-15.

After exploring the city, you could also drive to see the Hoover Dam about 40 minutes from Las Vegas. This place is a magnificent combination of nature, history and physics.

Los Angeles & Dana Point, California

Finish your road trip with celebrity spotting in Hollywood, a visit to Universal Studios and Six Flags Magic Mountain, and some well-deserved relaxation on the beach in Santa Monica.

We've also included a 7-day surf camp at Dana Point in this itinerary, where you can practice mastering the waves while getting to know other backpackers from around the world. Not a bad way to end your epic US adventure!

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