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Fly Drive USA

Route 66

Begins in Chicago, Illinois and ends in Los Angeles, California

  • 23 Days / 22 Nights
  • All year round

Begins in Chicago, Illinois and ends in Los Angeles, California

One of the most renowned driving routes in the world, historic Route 66 spans across North America, from Chicago in the east to Los Angeles in the west. Covering over 2,000 miles, it takes three weeks or longer to complete the journey in its entirety so we have created three options to choose from: the entire journey (Chicago to Los Angeles); Chicago to Albuquerque or Oklahoma City to Los Angeles.

The journeys shown are based on car rental, however motorbikes or motorhomes can be substituted should you prefer. Take a look at the options at the base of this page for more information.

  • Round trip scheduled flights
  • Intermediate 4 door car hire including insurances
  • Accomodations as stated

Pricing Information

With airlines and hotels regularly introducing special offers, we’ve elected to not display pricing on our website. In order to ensure that we give you the most competitive price for the itinerary you’re interested in we’ll apply the best rates, promotions and offers that are available when we receive your enquiry. Please contact us via email, telephone or our websites ‘make an enquiry’, and we’ll endeavour to provide you with a tailor-made quotation within one working day.

Pricing Information
Day 1, 2

Arrive Chicago

Depart the UK on your chosen scheduled flight to Chicago. Upon arrival, collect your rental car and proceed to your hotel. Chicago is one of the most popular US cities and it’s easy to see why. A myriad of attractions and the fabled ‘Magnificent Mile’ of shopping keep its visitors entertained and the cultural mix provides for fabulous dining options too.

Sightseeing in Chicago

Palmer House, A Hilton Hotel, Chicago
Day 3

Springfield, Illinois

202mi / 325km

Why not start today with breakfast at Lou Mitchell’s, a Chicago institution which has claimed to be “serving the world’s finest coffee” since 1923. There is some dispute about where Route 66 begins in Chicago, but a good place to start is the Route 66 sign on Adams Street, just west of its intersection with Michigan Avenue. The instantly recognizable Route 66 insignia hangs above a sign reading “BEGIN,” making this a perfect place to take your first trip selfie. A great first stop is Joliet, Illinois, where you can explore the Route 66 Museum to get to know the “Muffler Men,” giant fiberglass statues used along the Route in the 1960s to advertise auto repair shops, diners and other roadside attractions. See your first Muffler Man in Wilmington, the 9-meter Gemini Giant promoting the Launching Pad Drive-In Restaurant, then head to Dwight for a stop at Ambler’s Texaco Gas Station, once the oldest continually operated gas station on the route. As you pass through Pontiac, don’t miss its collection of murals of President Abraham Lincoln. Be sure to visit Pontiac’s Route 66 Hall of Fame and Museum, with its collection of vintage ads, signs and memorabilia, before arriving at tonight’s destination, Springfield. 

Day 4, 5

St Louis, Missouri

96mi / 154km

Before leaving Springfield today, visit the Oak Ridge Cemetery to see the Lincoln Tomb – the final resting place of President Lincoln. The 35-meter monument that marks his gravesite is decorated by four ornate sculptures that honor Civil War servicemen. Next, head to Litchfield for a quick stop at the Litchfield Museum & Route 66 Welcome Center before lunch at the Ariston Café. Open since 1935, it is among Route 66’s oldest restaurants. After lunch, make your way to St. Louis, Missouri, crossing the mighty Mississippi River on the New Chain of Rocks Bridge. Be sure to stop to explore the now pedestrianized old Chain of Rocks Bridge to enjoy beautiful greenery along the river. The eye-catching Gateway Arch National Park is a perfect first stop upon arriving in St. Louis. Take a 190-meter tram ride to the top of the tallest monument in the United States and be awed by breathtaking views. Explore the Museum at the Gateway Arch to learn about the history of the USA and maybe even take a riverboat cruise down the Mississippi. For dinner, explore the St. Louis restaurant scene. Famous for its ribs, the city has plenty of excellent barbeque spots.

Day 6

Springfield, Missouri

289mi / 465km

As you leave St. Louis this morning, stop at Ted Drewes and enjoy frozen custard for breakfast. Then, it’s on to Stanton in the Missouri Ozarks to Jesse James Wax Museum, where you can learn about the life and career of one of the USA’s most notorious outlaws before visiting his reputed hideout at Meramec Caverns. Take a guided walking tour of this seven-story natural wonder along natural walkways formed from limestone erosion over millions of years. Stop in Cuba to see the oldest continually operated motel on Route 66, the Wagon Wheel. An excellent place for lunch is Missouri Hick Bar-B-Que. Make one last stop in St. Robert for sweet treats at the famous Uranus Fudge Factory & General Store. Upon arrival in Springfield, Missouri, visit the Route 66 Car Museum, famed for its collection of vintage cars that would have once lined the route.

Day 7

Tulsa, Oklahoma

113mi / 182km

Depart Springfield and make a quick stop in Carthage to see the 66 Drive-In Theatre before heading to Galena, Kansas. While Route 66 only runs through about 20 meters of the state of Kansas, you’ll find some key stops along that stretch. Cars on the Route, once called Kan-O-Tex Service Station, has been transformed into a whimsical tribute to the animated movie “Cars.” Check out the mining boom truck, supposedly the inspiration for the tow truck character Tow Mater. Stop and pick up lunch at The Old Riverton Store, which has been operating since the start of Route 66. Take your sandwiches to Rainbow Bridge, which crosses Brush Creek, to admire the only Marsh arch bridge remaining on the route today. Head to Commerce, Oklahoma, for dessert at Dairy King, a family-owned drive-through housed in a charming old gas station. Next is one of the highlights of your journey: Ribbon Road, the narrowest and oldest segment of Route 66. As you near Tulsa today, you will pass through the town of Catoosa, home to the Blue Whale, a nostalgic roadside landmark.

The Mayo Hotel, Tulsa
Day 8, 9

Oklahoma City, Oklahoma

107mi / 172km

Have a leisurely start to your journey this morning as you enjoy the many Route 66 sites in Tulsa. At Buck Atom’s Cosmic Curios, a former gas station on the route, go memento shopping and snap a selfie with Muffler Man Buck Atom: Space Cowboy. Another famous Muffler Man nearby is the Golden Driller, a 22-meter-tall monument to Tulsa’s rich oil history. Stop for lunch at Flo’s Burger Diner and try their Signature Bomb Burger. As you leave town, make a stop at the Cyrus Avery Centennial Plaza, which pays homage to the Tulsa resident known as the “Father of Route 66.” Stroll the observation walkway for incredible views of the historic Route 66 Bridge as it stretches across the Arkansas River. As you pass through Stroud, stop at the Skyliner Motel for a photo under their towering red arrow sign. In Arcadia, visiting Pops 66 Soda Ranch is a must. Fuel up at the gas station and grab a bite at the restaurant, which offers over 600 choices of soda pop. If you’re driving past at night, you can’t miss this place: A giant soda bottle covered in neon lights stands outside. We have included two nights in Oklahoma City, so you have ample time to explore the plethora of attractions. Take time to truly discover the state capital and trace the routes of the original Route 66. Just off 23rd Street, right in the middle of Classen Boulevard, stands one of the city’s most iconic Route 66 landmarks – The Milk Bottle Grocery. Snap a photo of the giant milk bottle that sits atop the building. Don’t miss the Oklahoma State Capitol. The remarkable dome on top features a bronze statue of a Native American figure, standing over five metres tall and depicting characteristics of each of the state’s 38 federally recognized tribal nations. In the evenings, explore the historic Uptown 23rd District. Discover the nostalgic neon signs along the old route and stop for dinner at one of the many Asian-owned area restaurants, or try Cheever’s Café, famous for its upscale comfort food. 

Sheraton Oklahoma City Downtown Hotel
Day 10

Amarillo, Texas

260mi / 418km

Depart Oklahoma City, and cross the steel truss bridge over Lake Overholser as you leave town. Continuing along Route 66, stop in Clinton‘s Route 66 Museum to experience the story of the Mother Road as you listen to the big band music of the era, sit in a booth at a 1950s diner and learn about life on the road through images and sounds. As you cross the state line into Texas, stop at the gorgeous Tower Station and U-Drop Inn Café. This art deco edifice was once a popular gas station and café among Route 66 travellers. Today, it has been fully restored and houses a museum and gift shop. Make a quick photo stop in Groom, at the whimsical Leaning Tower of Texas, an unconventional water tower built to look like it will come crashing down at any moment. Other possible stops en route are the entertaining Sand Hills Curiosity Shop in Erick, the Devil’s Rope Barbed Wire Museum in McLean, and the VW Slug Bug Ranch in Conway, where five VW Beetles are buried nose-down in the ground.Tonight, in Amarillo, perhaps visit The Big Texan Steak Ranch, famous for its quirky architecture and its flame-grilled steaks.

Day 11, 12

Santa Fe, New Mexico

279mi / 449km

A short drive west of Amarillo is the famous Cadillac Ranch, a striking installation made up of ten graffiti-covered Cadillacs buried halfway in the dirt in the Texas desert. This psychedelic ode to cars is an iconic photo op. A short distance west, celebrate your arrival halfway down Route 66 at the Midpoint Café in Adrian. After lunch, travel west to the historic ghost town of Glenrio. The Glenrio Historic District straddles the border of Texas and New Mexico, and locals maintain that it was a filming location for the 1940 movie “The Grapes of Wrath.” You can still see the old Route 66 roadbed among the many now-unused historic buildings. Why not enjoy lunch at Del’s Restaurant in Tucumcari, New Mexico; it’s easy to find due to the giant cow outside. With its neon signs, kitschy Americana architecture and locally owned motels, Tucumcari is home to a cornucopia of photo ops showcasing what Route 66 is all about. Heading west, stop in the historic town of Santa Rosa to take a dip in the famous Blue Hole. Sightsee in the downtown plaza dominated by the stunning Guadalupe County Courthouse. We have allowed a full day in Santa Fe, which is America’s oldest state capital, to relax and explore.

Inn and Spa at Loretto, Santa Fe
Day 13, 14

Albuquerque, New Mexico

61mi / 98km

Departing Santa Fe en route to Albuquerque was once one of the most challenging parts of the journey, as the road descended 150 meters in just three kilometers thanks to 26 incredibly steep switchbacks. Why not venture off the freeway along the Turquoise Trail National Scenic Byway? You’ll enjoy breathtaking views from atop Sandia Crest, and pass through the mining towns of Los Cerrillos, Madrid and Golden. Why not start your Albuquerque experience with a relaxed dinner at the 66 Diner, housed in an old Phillips gas station. Again we have given you two nights to truly experience Albuquerque. This morning, tour the Old Town and Downtown areas of Albuquerque along the stretch of Old Route 66 now known as Central Avenue. Mustsees include the KiMo Theater, a marvel of Pueblo Deco architecture, and the San Felipe de Neri Church, one of the oldest surviving buildings in the city. Stop for lunch at the Dog House Drive In, which television buffs may recognize from “Breaking Bad” and “Better Call Saul.” After over 50 years, this restaurant remains much the same, serving hot dogs, hamburgers and milkshakes from a modest brick shack. The Dog House bears one of the most recognizable neon signs along the route, delighting visitors with its depiction of an elongated dachshund wagging its tail and chewing on a string of sausages. After lunch, visit the Historic Nob Hill neighborhood to explore Central Avenue, with its glowing neon lights and signs marking the location of Old Route 66. This area is well-known for its colorful nightlife and diverse restaurants; if you like Mexican cuisine, try the whimsical Range Café.

Day 15

Gallup, New Mexico

140mi / 225km

Head west again today and make your first stop in the tiny village of San Fidel to browse the Acoma Curio Shop. Famous for its adobe walls, mining style façade and tin roof, this little abandoned building is one of the most popular stops on Route 66. Continue to Thoreau, another small village along Route 66, defined by its Navajo roots and home to a local trading center for turquoise and silver jewelry and artisan rugs. The old Roy T. Hermans’ Garage and Service Station is a supreme selfie stop; while it’s no longer serving gas, the Hermans still run a repair garage out of this building. Soon you arrive in the old railroad town of Gallup on the western edge of New Mexico. Visit the historic El Rancho Hotel and drive down motel row, which sparkles with vintage neon motel signs.

Day 16, 17

Flagstaff, Arizona

186mi / 299km

Roll into Arizona and make a stop today at one of Route 66’s natural wonders, Petrified Forest National Park. Explore its almost otherworldly landscape along its 45-kilometer main road, which passes thorough the Crystal Forest Trail, an area with giant logs that have petrified to practically solid quartz, and the stunning Painted Desert, so named for its array of colors. Take time to visit Winslow to see La Posada Hotel. Opened in 1930 as one of the most luxurious hotels in the Southwest, this Arizona gem was restored to its former glory in the 1990s and is still one of the most popular stops along Route 66. The town of Winslow is full of treasures both historic and modern. Visit the Standin’ on the Corner Park on the corner of Kinsley and East 2nd Street, established to commemorate USA band The Eagles’ first hit single, “Take it Easy,” which mentions Winslow by name. The park brings the song’s lyrics to life with a statue of a guitar-bearing singer and a mural of “a girl” sitting “in a flatbed Ford” truck. Just outside of Winslow, stop to view Meteor Crater, where a meteorite fell to Earth some 50,000 years ago. Then make your way toward Flagstaff, being sure to stop for lunch at Miz Zip’s, a retro Route 66 institution serving up burgers and pies. After lunch, view the block-long mural at South San Francisco Street, or, if you want to explore more, take the self-guided tour from the Visitor Center. Flagstaff enjoys many iconic neon signs, including the exciting moving wagon and horses that decorate the Western Hills Motel. 

Little America Hotel, Flagstaff
Day 18

Kingman, Arizona

167mi / 269km

Take a short drive from Flagstaff to arrive in Williams. Drive down Main Street to view retro-chic signs, like the red car atop Cruiser’s Route 66 Café. The next stop is Seligman, another small Route 66 town full of colorful vintage gas stations, cafés and stores, all restored to their original glory. Stop at Delgadillo’s Snow Cap Drive-In, now a Guinness World Record holder for the “Largest Display of Milkshakes Varieties,” for a sweet treat. One of the most important stops along the route is Kingman, where the Arizona Route 66 Museum traces the history of the Mother Road. Cross the street to enjoy a plate of barbeque ribs at Mr. D’z Route 66 Diner. We have you overnighting in Kingman, however if Las Vegas is on your ‘hit list’ you may choose to drive north and have a night or two in “Sin City”.

Day 19

Barstow, California

207mi / 333km

Leaving Arizona behind, you cross the magnificent Mojave Desert en route towards California – which is the last state on the Route 66 journey. We suggest a stop at the small Wild West-style town of Oatman, where gift shops, saloon bars and live shows are sure to entertain, before crossing the Colorado River and arriving in California. As you pass through Amboy, make a stop at Roy’s Motel & Café to snap photos of its iconic neon sign and the Route 66 insignia on the highway. One hour west, you arrive in#t Barstow and The Route 66 “Mother Road” Museum housed in the historic Casa del Desierto, where you’ll admire artifacts and images of the old road.

Day 20, 21, 22

Santa Monica, California

131mi / 211km

Heading towards the Pacific Coast, Cajon Boulevard offers stunning mountain views of Cajon Pass as it joins up with Old Route 66. Continue to Downtown San Bernardino, where the First Original McDonald’s Museum offers a slice of Americana legend, as does the Route 66 map painted on the side of City Hall. The Wigwam Motel just outside town is a fun photo stop. Take Foothill Boulevard down the path of Old Route 66 to reach Pasadena, where you’ll find the only remaining historical mile marker on Colorado Boulevard. Next, cross the Colorado Street Bridge, which was the world’s highest cement bridge when completed in 1913. Head through Downtown Los Angeles and make a stop at Grand Central Market for lunch before joining Sunset Boulevard, where you’ll see historic buildings and spectacular views of Los Angeles. Follow Santa Monica Boulevard through West Hollywood to Beverly Hills and take a selfie at the Beverly Hills sign. Arrive in Santa Monica stopping at the corner of Ocean and Santa Monica Boulevard before heading to the Santa Monica Pier. There, you’ll find a plaque dedicated to Will Rogers, the renowned comedian and actor who inspired people to drive Route 66. Your journey comes to an end as you step onto the pier, where a sign marks the official end of the Mother Road! We have allowed a three night stay in Santa Monica for you to relax and enjoy L.A.’s many attractions.

Fairmont Miramar Hotel & Bungalows, Santa Monica
Day 23

Journey Home

13mi / 21km

Take the short drive to Los Angeles Airport, return your rental car and check-in for your flight back to the UK.

Shorter Durations

Should you not have a full 23 days available to do the full length of Route 66, then we can offer shorter duration trips for you to enjoy ‘the mother road’. Please see details below:

Duration: 15 days / 14 nights 

Starts Chicago and ends Albuquerque


Starts Oklahoma City and ends Los Angeles 

Other Route 66 Holiday Options

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.

Get in Touch

Our team of travel professionals focus on providing you with the very best advice when it comes to planning your holiday to the USA and Canada. They have experienced the destinations, hotels, tours and excursions for themselves, so if its expert advice and guidance backed by faultless customer service that you are looking for, you couldn’t’ be in safer hands. We will listen to your wish list of ideas as well as add our own personal recommendations to create a unique itinerary, personalised just for you.

For a quotation based on your preferred travel date and to check availability please contact one of our team of professional consultants who will be happy to assist you.

Our website features just some of the itineraries we offer. Tell us what your ideas are and we will create the holiday for you

Travel Agents

0333 323 9033 travel.agents@nats-uk.com

Direct Clients

0333 323 9099 sales.enquiries@nats-uk.com

How Can We Help?

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