Route 66 ~ USA

Chicago to LA

Self Drive Exploring

Embarking on a self-drive adventure along Route 66 is a journey filled with nostalgia, breathtaking landscapes, and a deep sense of American history.

The iconic “Main Street of America” stretches across eight states, offering a diverse tapestry of landscapes, from the bustling cityscapes of Chicago to the vast deserts of Arizona. Driving along Route 66 allows you to immerse yourself in the unique culture and charm of each town, discovering quirky roadside attractions, classic diners, and vintage motels. It’s a chance to experience the freedom of the open road, creating your own pace and stopping at iconic landmarks like the Grand Canyon or Cadillac Ranch. The sense of independence and the opportunity to witness the changing scenery make a self-drive through Route 66 an unforgettable and personalised adventure, providing a deeper connection to the rich cultural tapestry that defines this historic route.

All the things you need to know

Today you begin your journey by boarding your international outbound flight to Chicago. On arrival in Chicago make your own way to your downtown hotel. The remainder of the day is free for you to settle in. You could relax in Millennium Park and admire its art installations and fountains, visit one of the city’s museums or head out to a local pizzeria for your first taste of an authentic Chicago deep dish pizza.

Enjoy a full day at leisure exploring the ‘Windy City’, Chicago. There’s plenty to do in this exciting metropolis; we recommend a trip to the Skydeck at the top of Willis Tower or, for a different view of the city skyline, take a boat trip on Lake Michigan at sunset.


This morning marks the start of your 3,945 km (2,451 mile) drive to California. Collect your car which comes fully-covered; road maps and a sat-nav are included. Heading out of Chicago on Route 66, your three and a half hour drive to the pretty city of Springfield, Illinois takes you through grassy farmlands and past small towns that dot the rural landscape. Springfield is Illinois’ state capital and was the former residence of Abraham Lincoln. Making an early start allows free time to explore Lincoln’s presidential museum, home and final resting place at Oak Ridge Cemetery.


Departing Springfield, this morning’s two-hour drive takes you through rolling farmland and patchwork fields into St. Louis, Missouri. The afternoon is free for you to explore this historic city at leisure. There’s plenty to see and do in St. Louis; the famous Gateway Arch represents the city’s moniker, the ‘Gateway to the West’, and the City Museum and Lafayette Square are well worth a visit.


Today, you’ll have a chance to explore St Louis. The City Museum, Anheuser-Busch Brewery, and the National Blues Museum are great options to spend an afternoon exploring. Or, if the Cardinals are in town, you can watch a baseball game in Busch Stadium.


Leave the Mississippi River behind and travel along Route 66 through the scenic beauty of the Ozark Mountains. The Ozarks are the second oldest mountains in the world and offer beautiful vistas and great walking opportunities for visitors. Around a four-hour drive from St. Louis is Springfield, Missouri, where you’ll stop for the night.


Today’s journey sees you drive almost 483 km (300 miles) west to Oklahoma City — a journey of around five hours. Crossing the state border, you officially enter the American South; the land around you becomes increasingly arid and dusty as you pass through land that was once the haunt of American Indians, later the territory of cowboys and outlaws. On arrival at your hotel, tuck into a hearty meal and put your feet up after your long journey.


Your journey continues for another 418 km (260 miles) west across the state border into Texas to Amarillo. It’s on this four and a half hour journey that you’ll find some wonderful icons of Route 66, including the National Route 66 Museum, which is home to an array of antique cars, historical artefacts and a replica drive-in theatre.


A day at leisure to explore the beauty of Santa Fe

There is plenty to see on your drive into Arizona; you’ll pass Petrified Forest National Park, a huge landscape dominated by red, barren vistas of the Painted Desert and thousands of acres of petrified wood. Your destination today is the town of Winslow, which was a thriving town on the Santa Fe Railway and made famous by the Eagles’ song ‘Take It Easy’.


Today’s four-hour drive will take you to the Grand Canyon, passing the world’s first proven meteor crater enroute. You may wish to stop in the town of Flagstaff for lunch, before an afternoon free to explore the canyon.


Spend a full day exploring Grand Canyon National Park. You may wish to take a helicopter trip over the canyon, take a hike down into the valley, or simply gaze in awe at the sight of the canyon at sunrise or sunset.


Continue your drive west for another 483 km (300 miles) into Nevada. It’s worth making an early start as there’s lots to see on this five and a half hour journey. Detouring from the main highway at Seligman allows you to travel along the original Route 66, which is peppered with abandoned motels, derelict gas stations, and the outdoor Route 66 Car Museum. Venturing deeper into the desert, you’ll have the opportunity to stop at the Hoover Dam, which is located around 56 km (35 miles) south of Las Vegas.


Spend a full day at leisure exploring the spectacle that is Las Vegas. Visit one of the many themed casinos, admire the bright lights and take in a show from some of the world’s most famous performers.


Complete your epic journey with your final 435 km (270 mile) drive to Los Angeles. A journey of around six hours, you’ll travel through the Californian desert for much of the day, passing by the Mojave National Preserve; a sweeping desert landscape punctuated by wildflowers and Joshua trees. On arrival in Los Angeles, return your car to the depot and make your own way to your hotel.


Enjoy a full day at leisure exploring California’s largest city, Los Angeles. This cosmopolitan city offers a diverse range of shops, restaurants and nightlife as well as world-renowned art galleries, beaches and film studios. Don’t miss a shopping trip to Beverly Hills, explore the celebrity haunts of Hollywood or just relax on the golden sands of Santa Monica.


Enjoy a last morning at leisure in Los Angeles then make your way to the airport in time for your onward flight.

  • Admire the beaches, architecture and nightlife of Chicago :
    Chicago is a melting pot of architectural marvels, from the sleek lines of modern skyscrapers to the timeless elegance of historic landmarks. Immerse yourself in the cultural vibrancy of this city, where a rich history and diverse communities come together to create an unparalleled urban experience. As you traverse the streets, the city’s iconic skyline and renowned nightlife add an extra layer of allure, making it a destination that seamlessly blends beachside relaxation, architectural wonder, and lively entertainment.
  • Visit the Grand Canyon : Venture west to witness the awe-inspiring grandeur of the Grand Canyon. Nature’s masterpiece, the Grand Canyon captivates with its breathtaking scale and mesmerising hues. Standing on the rim, you’ll be transported to a realm where time seems to stand still, and the sheer magnitude of the canyon’s depths leaves an indelible mark on your soul.
  • Petrified Forest National Park : As you traverse the trails, the ancient petrified wood, vibrant badlands, and unique geological formations unfold before you, creating a sensory experience that is both grounding and transcendent.
  • Las Vegas : Shift gears as you make your way to the pulsating heart of entertainment and glamour – Las Vegas. The city of lights, excitement, and endless possibilities, Las Vegas beckons with its vibrant nightlife, world-class shows, and iconic casinos. A city that never sleeps…
  • LA : Conclude your journey in the laid-back yet dynamic city of Los Angeles, where the Pacific Ocean meets the cityscape in a seamless blend of natural beauty and urban sophistication. Whether you choose to bask in the sun on the sandy beaches, explore the architectural wonders of Hollywood, or indulge in a shopping spree on Rodeo Drive, Los Angeles offers a diverse range of experiences. 
  • Scheduled International Flights : Package includes your flights from A – B

  • Fully insured vehicle hire : So you don’t have to worry and can explore at your own pace.

  • All accommodation : Choose from a wide selection of accommodation in each stop.

  • 24 Hour support whilst you travel : We are here with you for your entire trip, so if you need anything, you don’t need to worry, we’ve got you.
  • Chicago:
    • Layered clothing for the variable weather, including a light jacket and jumpers.
    • Comfortable walking shoes for exploring the city.
  • Grand Canyon:
    • Sturdy hiking boots for exploring trails.
    • Lightweight, moisture-wicking clothing for daytime hikes.
    • Warmer layers for cooler evenings.
  • Las Vegas:
    • Light and breathable clothing for the desert heat. It’s the desert, so don’t forget that evening temperatures drop and it can be chilly at certain times of the year.
    • Swimsuit for poolside relaxation.
  • Los Angeles:
    • Casual and stylish clothing suitable for the mild climate.
    • Beachwear if you plan to relax on the coast.


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We are here to help. Our travel experts will organise and book your dream holiday.
call us today or complete our online enquiry form to start your next adventure.

Let's Chat

We are here to help. Our travel experts will organise and book your dream holiday.
call us today or complete our online enquiry form to start your next adventure.