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Historic Route 66 Fly Drive Holiday

16 days from £1,499pp

Chicago - St Louis - Springfield - Oklahoma City - Amarillo - Albuquerque - Holbrook - Grand Canyon - Santa Monica / Los Angeles

Drive the iconic Route 66, from Chicago to the Santa Monica Pier on this once-in-a-lifetime fly drive adventure. Your journey will take you over 2,400 miles through the contrasting landscapes of the USA, with famous quirky Route 66 landmarks to spot along the way.

If you're looking for a longer trip, check out our 21 day Route 66 fly drive holiday itinerary.

Route 66 PDF itinerary  

Holiday Highlights

  • Take in the iconic skyscrapers and blue-green rivers of Chicago.
  • Sample some of America’s most famous diners and bizarre roadside attractions.
  • Go for a hike or stop at one of the many roadside view points at the Grand Canyon, one of the seven natural wonders of the world!

Remember, we can tailor-make your fly drive holiday to suit your needs, including car rental with our trusted car hire partner Alamo. You can contact our travel experts today on 0208 290 9751.

Holiday Map

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Detailed Itinerary

Day 1: London to Chicago

Fly into Chicago, your starting destination to begin your epic Route 66 journey. On arrival, transfer independently to your hotel. Stay 2 nights at Best Western Grant Park (or similar).

Day 2: Chicago

Step outside today and experience mile after magnificent mile of the Windy City. Stand on the corner of Michigan and Adams, marked as the starting point of historic Route 66. Enjoy coffee and a big breakfast at Lou Mitchell’s, a Chicago institution since 1923 and a must for Route 66 travellers. Stroll the lakefront, browse the shops, bike the parks, grab a Chicago Dog, or explore the incredible sights and architectural treasures including the impressive skyline views at the Willis Tower.

Day 3: Chicago - St Louis (approx. 296 miles)

Today, pick up your Alamo rental car from the depot to start your drive along Route 66. Begin your journey by following the traditional east-to-west path of Route 66 from Chicago to St Louis. En route, be sure to stop in Pontiac and other iconic stops along the way in Illinois, such as the Cozy Dog Drive-In, the birthplace of the corn dog, and explore the legacy of Abraham Lincoln with a visit to the Lincoln Home National Historic Site. Once in St. Louis you may have time to visit the Gateway Arch, the tallest monument in the USA, take a tour of one St Louis's many local breweries or spend the afternoon strolling the many boutiques on the Delmar Loop. Stay 1 night at Red Roof Inn St. Louis (or similar).

Day 4: St. Louis – Springfield (Missouri)(approx. 210 miles)

Continue through the Ozark Highlands to Springfield, Missouri, recognised as the birthplace of Route 66 in 1926. En route, be sure to stop at Meramec Caverns in Stanton, an extensive set of natural limestone caves whose formations and colours are as unique as they are beautiful. Stay 1 night at Best Western Route 66 (or similar).

Day 5: Springfield - Oklahoma City (approx. 310 miles)

This morning, travel south-west via Kansas, the shortest stretch of Route 66's eight-state run on your drive to Oklahoma City. Along the way, stop to see many of the famous Route 66 landmarks such as the Blue Whale in Catoosa, Oilman Driller in Tulsa, Route 66 motels and gas stations in Stroud & Chandler, POPs and the Round Barn in Arcadia, and Milk Bottle in Oklahoma City. Consider Ann’s Chicken Fry House as the place for a delicious chicken fried steak dinner. Stay 1 night at Howard Johnson Express Inn (or similar).

Day 6: Oklahoma City - Amarillo (approx. 260 miles)

Continue through Oklahoma to Amarillo, located in the flat plains of the Texas Panhandle, stopping en route at the Route 66 Museum in Clinton where you can experience six decades of Route 66 history and at U-Drop Inn Café, whose towering spire is still a reminder of the booming business it once saw. Once in Amarillo, be sure to visit Big Texas Steak Ranch where only the very hungry should attempt their 72oz. steak challenge. Stay 1 night at Best Western Amarillo Inn (or similar).

Day 7: Amarillo - Albuquerque (approx. 270 miles)

Before leaving Amarillo visit the Cadillac Ranch, where you can see a unique display of art featuring a row of ten colourfully painted Cadillac cars buried grille first in the ground. Continue to the MidPoint Café in Adrian, located at the halfway point of Route 66 and famous for its “ugly crust” pies. From Adrian, follow Route 66 to Albuquerque in New Mexico. Stay 3 nights Best Western Plus Rio Grande Inn (or similar).

Day 8: Albuquerque

Located virtually in the centre of New Mexico, Albuquerque spreads north and south along the banks of the Rio Grande and is by far the state’s largest city. Spend the day exploring Central Avenue, a treasure trove of Route 66 landmarks and one of the original Route 66 towns.

Day 9: Day visit to Santa Fe from Albuquerque (approx. 116 miles)

To get a true sense of the Old Route 66, take a detour to Santa Fe, the oldest capital in the US. Although it lost its place on Route 66 in 1938, it remains one of the most picturesque cities in the state. Plan a visit to one of Santa Fe’s famous art galleries and museums full of traditional and contemporary art, or shop for authentic creations you just won’t find anywhere else.

Day 10: Albuquerque to Holbrook (approx. 260 miles)

Travel to Holbrook via the Petrified Forest National Park, the only National Park containing a section of Route 66. Catch the sunset over the Painted Desert from Kachina Point at the park. Once in Holbrook, stop at the Wigwam Motel whose steel and concrete tepees feature modern conveniences and have been welcoming guests since the 1950’s. Stay 1 night at Magnuson Adobe Inn (or similar).

Day 11: Holbrook to Grand Canyon/Williams (approx. 180 miles)

Continue to Meteor City, a true vintage trading post whose distinctive dome can be seen for miles along this stretch of Route 66. Pass through Flagstaff and Williams en route to Grand Canyon National Park, where you can spend the day discovering the distinct South Rim of the Canyon. Stop at one of the numerous overlooks, walk part of the Rim Trail, or climb to the top of a stone Watchtower for panoramic views that extend over 100 miles on clear days. Stay 1 night at Holiday Inn Williams (or similar).

Day 12: Williams to Las Vegas (approx. 300 miles)

Leave the town of Williams as you make your way to Seligman, the first stop heading west on the longest, uninterrupted stretch of Route 66. Continue through Kingman whose old Route 66 cafés and motels still flourish today, then on to one of Arizona’s famous treasures, the Hoover Dam before ending your journey in Las Vegas. Stay 2 nights at The Quad (or similar).

Day 13: Las Vegas

Enjoy a full day to explore the famous Strip, with its mega resorts and flashing neon lights. Place a bet at one of the many casinos, dine at world-class restaurants, catch the latest must-see show, shop designer boutiques, ride a rollercoaster, lay by the pool… the list goes on. With so much to do, 24 hours in a day hardly seems like enough.

Day 14: Las Vegas to Santa Monica, Los Angeles (approx. 290 miles)

This morning, set out through the Mojave Desert for Calico Ghost Town, California’s authentic silver mining town and one of the few original mining camps of the Old West. Re-join Route 66 in Barstow where a collection of historic artefacts are on display at the Route 66 Mother Road Museum. Continue through Pasadena and Los Angeles to Santa Monica for a true Hollywood ending to your cross-country journey. Park and walk the last few blocks to view the “End of the Trail” sign on Santa Monica's Pier. This sign officially marks the western end of historic Route 66. Stay 2 nights at Crowne Plaza LAX (or similar).

Day 15: Los Angeles

Spend the day strolling along the beaches of Santa Monica or browsing the trendy and boutique shops along Third Street Promenade. Or, why not further explore LA, with Hollywood, Beverly Hills, Universal Studios Hollywood and Anaheim’s original Disneyland Park all located within easy driving distance.

Day 16: Los Angeles to London

Return your rental car at Los Angeles International Airport prior to your departure flight to London.

(read more...)


Included in your Fly Drive Holiday

  • Hotel accommodation
  • Economy flights
  • Airport taxes, fuel & duty
  • Car rental where stated
  • Any applicable offers

Not included: Airport transfers, car hire one-way drop off fees, meals, sightseeing & personal expenses.

Flights from regional UK airports available

Remember, we can tailor-make your holiday to suit your needs, contact our travel experts today, call us on 0208 290 9751.


Deposits from £59pp 

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