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Based on two adults, travelling from London Heathrow and departing May 2027. Alternative Dates & Departure Airports Available Upon Request. Price includes all mandatory taxes and fees.
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Get your Kicks on Route 66 and experience one of the world’s most legendary road trips. From Chicago to Los Angeles, this iconic 2,000-mile journey takes you through the heart of America, with classic roadside towns, historic landmarks, vibrant cities and unforgettable landscapes along the way.
Our 14-day Route 66 fly drive makes it possible to experience the complete Mother Road in just two weeks. We’ve planned the route for you, with carefully selected accommodation and a car rental included, so you can concentrate on enjoying the journey.
Follow the original Route 66 itinerary from east to west and discover the places, people and stories that have made this famous highway a must-do USA road trip. From Chicago’s legendary start point to the bright lights of Los Angeles, every day brings something new.
If you have more time, our Route 66 Extravaganza gives you three weeks to explore at a more relaxed pace, with extra nights in many of the destinations along the way.
Prefer two wheels? We also offer guided and self-drive motorbike holidays along Route 66, as well as motorhome options, giving you even more ways to experience America’s legendary Mother Road.
Depart the UK on your included scheduled flight to Chicago, the starting point of your unforgettable Route 66 fly drive holiday. On arrival, make your own way to your centrally located hotel and settle in.
With your first evening at leisure, why not head out and experience a taste of Chicago? Enjoy dinner at one of the city’s many excellent restaurants, take an evening stroll along the Chicago Riverwalk or simply soak up the atmosphere of this vibrant American city.
You could also take a short walk towards Millennium Park to see the famous Cloud Gate sculpture, better known as “The Bean”, beautifully lit up after dark.
It’s the perfect introduction to Chicago before your full day of sightseeing tomorrow and the start of your Route 66 adventure.
Enjoy a full day to discover Chicago, the exciting starting point of your Route 66 holiday. With the day free to explore at your own pace, you can choose the sights and experiences that appeal to you most.
Take in the city’s famous skyline from the top of Willis Tower, stroll beside the shores of Lake Michigan or visit Millennium Park and see the iconic Cloud Gate sculpture, known as “The Bean”.
Sports fans can visit legendary Wrigley Field, while shoppers can explore the famous Magnificent Mile. For a relaxed afternoon, head to Navy Pier, enjoy the waterfront views or simply soak up the atmosphere of this vibrant city.
Chicago’s neighbourhoods each have their own character too. Discover the historic streets of Old Town, explore the creative side of Wicker Park or experience the stylish Gold Coast.
With world-class attractions, fantastic restaurants, great shopping and an incredible skyline, Chicago is the perfect place to begin your Route 66 road trip. Make the most of your free day before hitting the road and following the legendary Mother Road west.
Your Route 66 road trip begins today! Before hitting the road, why not enjoy breakfast at Lou Mitchell’s, a Chicago institution that has been serving hungry travellers since 1923?
After breakfast, collect your car rental and set off on your Route 66 adventure. There is some debate about the exact starting point of the original highway, but the Route 66 “BEGIN” sign on Adams Street is the perfect place to start. Stop for a photo and capture your first selfie on the legendary Mother Road.
Your first major stop is Joliet, home to the Route 66 Museum. Discover the history of the highway and learn about the famous Muffler Men, the giant fibreglass figures that once stood outside diners, garages and roadside attractions.
Continue to Wilmington to see the impressive Gemini Giant, a nine-metre Muffler Man that once advertised the Launching Pad Drive-In. Then head to Dwight and stop at Ambler’s Texaco Gas Station, one of the most famous historic service stations on Route 66.
Continue west to Pontiac, where colourful murals celebrate the life of Abraham Lincoln. Don’t miss the Pontiac Route 66 Hall of Fame and Museum, packed with vintage signs, advertisements and Route 66 memorabilia.
Finally, continue to Springfield, the state capital of Illinois and your overnight stop. With classic roadside attractions, historic landmarks and plenty of Route 66 nostalgia, today offers a fantastic introduction to the Mother Road.
Before leaving Springfield, take time to visit Oak Ridge Cemetery and the impressive Lincoln Tomb, the final resting place of President Abraham Lincoln. The 35-metre monument is a fascinating stop for history lovers and a memorable way to begin the day’s journey.
Continue along Route 66 to Litchfield, where you can visit the Litchfield Museum & Route 66 Welcome Center and discover more about the Mother Road. Then stop for lunch at the historic Ariston Café, which has been welcoming Route 66 travellers since 1935.
This afternoon, cross the mighty Mississippi River and enter Missouri on your journey to St. Louis. Take time to explore the historic Chain of Rocks Bridge, now pedestrianised and offering beautiful views along the river.
On arrival in St. Louis, make the Gateway Arch National Park your first stop. The city’s iconic Gateway Arch rises 190 metres above the Mississippi and is one of America’s most recognisable landmarks. Take the tram to the top for spectacular views across St. Louis and the Mississippi River.
You can also explore the museum beneath the Arch or enjoy a relaxing riverboat cruise before discovering the city’s famous food scene. St. Louis is known for its barbecue and ribs, making it the perfect place to round off another memorable day on your Route 66 road trip.
Leave St. Louis behind and continue your Route 66 road trip through the beautiful Missouri Ozarks. Start the day with a true St. Louis tradition at Ted Drewes, where you can enjoy its famous frozen custard before hitting the road.
Continue to Stanton and step into the past at the Jesse James Wax Museum, where you’ll discover the story of one of America’s most notorious outlaws. Nearby, explore Meramec Caverns, a spectacular seven-level cave system once linked to the legend of Jesse James. Follow the guided walking trail through impressive limestone formations created over millions of years.
Back on the Mother Road, stop in Cuba to see the historic Wagon Wheel Motel, one of the oldest continuously operating motels on Route 66. For lunch, tuck into some authentic Missouri barbecue at Missouri Hick Bar-B-Que.
Continue to St. Robert for one of Route 66’s most unusual stops: Uranus Fudge Factory & General Store. Pick up a sweet treat and enjoy one of the quirky roadside attractions that make this highway so memorable.
Finally, arrive in Springfield, Missouri, the birthplace of Route 66. Don’t miss the Route 66 Car Museum, home to an impressive collection of classic and vintage automobiles that capture the spirit of America’s great road trip.
With legendary characters, historic motels, spectacular caves and wonderfully quirky roadside attractions, today is Route 66 at its most entertaining.
Today your Route 66 adventure takes you through Kansas and into Oklahoma, with some of the most colourful and quirky stops on the Mother Road along the way.
Begin with a quick stop in Carthage to see the historic 66 Drive-In Theatre before crossing into Kansas. Although Route 66 covers only a short stretch of the state, it is packed with classic roadside attractions. In Galena, see Cars on the Route, a former service station transformed into a tribute to the movie Cars, before continuing to the historic Old Riverton Store and Rainbow Bridge.
Cross into Oklahoma and stop in Commerce for a sweet treat at the nostalgic Dairy King, housed in a former gas station. Then experience one of the most memorable sections of the Mother Road: Ribbon Road, a narrow and historic stretch of original Route 66.
Continue towards Tulsa, where Route 66 history comes to life. See the famous Blue Whale of Catoosa, then explore some of Tulsa’s iconic roadside landmarks, including Buck Atom’s Cosmic Curios and the towering Golden Driller.
Don’t miss Cyrus Avery Centennial Plaza, named after the Tulsa resident known as the “Father of Route 66”. The observation walkway offers great views of the historic Route 66 Bridge over the Arkansas River.
As you continue west, stop in Stroud for a photo at the Skyliner Motel before reaching Arcadia and the famous Pops 66 Soda Ranch. With hundreds of sodas to choose from and its giant neon bottle glowing above the roadside, it’s one of the most recognisable stops on the Mother Road.
Your journey ends in Oklahoma City, where you’ll have time to explore the state capital and discover even more Route 66 history. Look out for the famous Milk Bottle Grocery, visit the Oklahoma State Capitol and explore the historic Uptown 23rd District, where vintage neon signs and local restaurants bring the old highway to life.
From quirky roadside attractions and classic diners to historic landmarks and original stretches of highway, today showcases exactly why a Route 66 road trip is such an unforgettable American adventure.
Leave Oklahoma City behind and continue your Route 66 road trip west towards Texas. Cross the historic steel truss bridge over Lake Overholser before following the Mother Road through the Oklahoma countryside.
Your first major stop is the Route 66 Museum in Clinton, where you can step back in time and discover the story of America’s most famous highway. Vintage music, 1950s diner scenes, photographs and memorabilia bring the golden age of Route 66 to life.
Cross the state line into Texas and stop at the beautifully restored Tower Station and U-Drop Inn Café in Shamrock. This striking Art Deco landmark was once a popular stop for Route 66 travellers and is now a museum and gift shop.
Continue west with a photo stop at the wonderfully quirky Leaning Tower of Texas in Groom, a water tower designed to look as though it’s about to topple over. Depending on your route and timing, you could also discover attractions such as the Sand Hills Curiosity Shop, Devil’s Rope Barbed Wire Museum or the VW Slug Bug Ranch.
Arrive in Amarillo, where your Route 66 adventure continues with plenty of time to explore. For dinner, why not experience the legendary Big Texan Steak Ranch, famous for its larger-than-life Texas atmosphere and flame-grilled steaks?
From nostalgic museums and Art Deco landmarks to wonderfully eccentric roadside attractions, today delivers another unforgettable taste of classic Route 66.
Continue your Route 66 road trip west from Amarillo, with some of the Mother Road’s most iconic sights and roadside attractions waiting along the way.
Just outside Amarillo, stop at the famous Cadillac Ranch, where ten graffiti-covered Cadillacs are buried nose-first in the Texas desert. This colourful art installation is one of the most recognisable sights on Route 66 and a fantastic photo opportunity.
Continue to Adrian, where you’ll reach the Midpoint Café, marking the halfway point between Chicago and Los Angeles. Take a moment to celebrate reaching the middle of your Route 66 adventure before continuing west into New Mexico.
Your journey takes you through the historic ghost town of Glenrio, which straddles the Texas-New Mexico border. With its abandoned buildings and sections of the original road still visible, it offers a fascinating glimpse into the early days of Route 66.
Continue to Tucumcari, one of New Mexico’s classic Route 66 towns. Its colourful neon signs, vintage motels and nostalgic Americana make it a wonderful place to stop, explore and take photos. You could also enjoy lunch at Del’s Restaurant, recognised by the giant cow outside.
Travel onwards to Santa Rosa, where you can take a refreshing dip in the famous Blue Hole, a crystal-clear natural spring. Then continue towards Santa Fe, one of America’s oldest and most distinctive cities.
As you arrive in Santa Fe, the character of your journey begins to change. Discover adobe architecture, historic plazas, vibrant art galleries and the unique blend of Native American, Spanish and Mexican influences that make the city so special.
From iconic Route 66 landmarks and quirky roadside attractions to the distinctive culture of Santa Fe, today offers an exciting mix of classic Americana and New Mexico’s unique character.
Leave Santa Fe behind and continue your Route 66 road trip towards Gallup, with a fantastic mix of mountain scenery, historic towns and classic Mother Road attractions along the way.
For a more scenic journey, leave the freeway behind and follow the Turquoise Trail National Scenic Byway. This beautiful route takes you through the historic mining towns of Los Cerrillos, Madrid and Golden, with spectacular views across the New Mexico landscape. If time allows, continue towards Sandia Crest for breathtaking mountain views.
Arrive in Albuquerque, where Old Route 66 follows Central Avenue through the heart of the city. Explore the historic Old Town and Downtown districts, and look out for the KiMo Theater, an impressive example of Pueblo Deco architecture, and San Felipe de Neri Church, one of Albuquerque’s oldest surviving buildings.
Film and television fans can also make a quick stop at the Dog House Drive In, recognised from Breaking Bad and Better Call Saul. Its distinctive neon sign and classic diner menu make it a fun Route 66 photo stop.
Back on the road, continue west to San Fidel and the atmospheric Acoma Curio Shop, one of the Mother Road’s memorable roadside landmarks. Further west, stop in Thoreau, a small community with strong Navajo connections and a long tradition of turquoise, silver jewellery and artisan crafts.
Another great photo opportunity is Roy T. Herman’s Garage and Service Station, a beautifully preserved Route 66 landmark that still operates as a repair garage.
Finally, arrive in Gallup, a historic railroad town on the western edge of New Mexico. Take a drive along Motel Row, where vintage neon signs capture the nostalgic spirit of Route 66, and look out for the famous El Rancho Hotel, once a favourite stop for Hollywood stars travelling through the region.
Today’s journey showcases the incredible variety of New Mexico’s Route 66, from mountain scenery and historic communities to vintage diners, neon signs and classic roadside landmarks.
Today your Route 66 road trip crosses into Arizona, where spectacular desert scenery and iconic Mother Road attractions await.
One of the highlights is Petrified Forest National Park, home to an extraordinary landscape of colourful desert scenery and ancient petrified wood. Follow the park road through the Painted Desert and stop at the Crystal Forest, where huge petrified logs have been transformed into quartz-like stone over millions of years.
Continue to Winslow, one of Arizona’s most famous Route 66 towns. Visit the beautifully restored La Posada Hotel, a historic railway hotel dating back to 1930, then head to Standin’ on the Corner Park. Made famous by The Eagles’ song Take It Easy, this quirky landmark is an essential Route 66 photo stop.
Just outside Winslow, discover Meteor Crater, the enormous impact site created when a meteorite struck the Arizona desert around 50,000 years ago.
Continue towards Flagstaff, stopping for lunch at Miz Zip’s, a much-loved Route 66 diner serving classic American favourites. On arrival in Flagstaff, explore the historic downtown area and discover its colourful Route 66 murals and vintage neon signs.
If you have time, follow the self-guided Route 66 trail from the Visitor Center and look out for the distinctive moving wagon and horses at the Western Hills Motel.
With the spectacular Painted Desert, Petrified Forest, Meteor Crater and some of Arizona’s most nostalgic Route 66 landmarks, today is a fantastic introduction to the Grand Canyon State.
Today your Route 66 road trip continues through some of Arizona’s most nostalgic towns before crossing into Nevada and the bright lights of Las Vegas.
Start with a short drive to Williams, one of the best-preserved Route 66 towns in Arizona. Cruise along Main Street and look out for colourful vintage signs and classic roadside attractions, including the famous red car outside Cruiser’s Route 66 Café.
Continue to Seligman, a charming Route 66 town filled with colourful cafés, vintage shops, restored gas stations and classic Americana. Stop at the legendary Delgadillo’s Snow Cap Drive-In for a fun photo and a sweet treat.
Next, head to Kingman, an important stop on the Mother Road. Visit the Arizona Route 66 Museum to discover the story of this legendary highway, then enjoy a classic American lunch at Mr. D’z Route 66 Diner.
From Kingman, leave Route 66 behind and cross into Nevada, making your way to the excitement of Las Vegas. After the nostalgic roadside attractions of Arizona, the bright lights and energy of the Las Vegas Strip provide a spectacular change of pace.
We’ve included two nights in Las Vegas, giving you time to relax in the Nevada sunshine and enjoy the city’s famous attractions. Explore the themed hotels along the Las Vegas Strip, sample the incredible choice of restaurants or take in one of the city’s world-famous shows.
With the final leg of your Route 66 adventure still ahead, Las Vegas provides the perfect opportunity to take a break before continuing west through California towards the Pacific Coast and Santa Monica.
Leave Las Vegas behind and cross the spectacular Mojave Desert as your Route 66 road trip reaches California, the final state on your journey.
Continue to Barstow and the Route 66 “Mother Road” Museum, housed in the historic Casa del Desierto. Discover vintage photographs, memorabilia and stories from the golden age of America’s legendary highway.
Follow historic sections of Route 66 through the Cajon Pass towards San Bernardino. Here, discover more Mother Road history, including the Original McDonald’s Museum, the colourful Route 66 mural on City Hall and the famous Wigwam Motel.
Continue along Old Route 66 through Pasadena, where you can see the historic mile marker on Colorado Boulevard and cross the impressive Colorado Street Bridge. Then travel through Los Angeles, with the option to stop at Grand Central Market for lunch.
Follow Sunset Boulevard through Los Angeles and West Hollywood before continuing into Beverly Hills. Take a photo at the famous Beverly Hills sign before following Santa Monica Boulevard towards the Pacific Coast.
Finally, arrive in Santa Monica, where the Route 66 adventure reaches the Pacific Ocean. Head to the iconic Santa Monica Pier and look for the sign marking the western end of the Mother Road.
You’ve travelled from Chicago to Santa Monica, following one of America’s most legendary highways. With two nights in Santa Monica, there’s plenty of time to celebrate your journey and enjoy the best of this beautiful Southern California beach city.
Enjoy a final morning in Santa Monica before your journey home. Take a leisurely stroll along the famous Santa Monica Pier, relax on the beach or enjoy breakfast overlooking the Pacific Ocean. If you have time, explore the shops and cafés around Third Street Promenade before making your way to Los Angeles International Airport.
Return your hire car and check in for your included scheduled flight back to the UK.
From the skyscrapers of Chicago to the Pacific Ocean at Santa Monica, you’ve travelled almost 2,000 miles along the legendary Mother Road.
Along the way, you’ve experienced historic towns, classic diners, neon-lit motels, spectacular desert landscapes and some of America’s most exciting cities. From St. Louis and Santa Fe to Flagstaff and Las Vegas, every mile has added another chapter to your unforgettable Route 66 fly drive adventure.
Your journey may be over, but the memories of this incredible Chicago to Santa Monica road trip will last a lifetime.
These fly drives are flexible, so should you wish to make changes please let us know and we will create your chosen itinerary.
Should you prefer making your journey by motorhome, we have a selection of itineraries for you to choose from. The itinerary can also be adapted to suit your duration and route choice, plus we have a selection of RV sizes to ensure the perfect fit for you.
Our Route 66 motorbike holidays are fully escorted by an experienced guide. They can also be self-guided should you prefer or, we can arrange motorbike rental so you can wander wild and free.
Our team of experienced travel professionals are here to help. We'll help you with itinerary planning and provide you with a quotation.
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