Route 66 Fly Drive

Chicago • St Louis • Oklahoma • Springfield • Albuquerque • Las Vegas • Santa Monica

A road trip across America is something that most people long to do and with this Drive America option you can drive from Chicago on the shores of Lake Michigan to the golden beaches of Santa Monica and follow the historic and iconic Route 66 to get there.
On this road trip you can take in the Great Lakes of the north, the Ozark Mountains, the Great Plains, the Mojave Desert and the Pacific Ocean and as you travel across these diverse landscapes you will get to see some fascinating places and meet some wonderful people. In Missouri visit the Meramec Caverns, once used as a hideout by the outlaw Jesse James, while in Arizona you can drive the Historic Route 66 through the Petrified Forest National Park, stop by Calico Ghost Town and see what life was like in the mining towns of the Old West and at the end of the Santa Monica Pier see the ‘End of the Trail’ sign that marks the end of Historic Route 66.
With stops in places like Oklahoma City, Amarillo, Albuquerque and Santa Fe this holiday gives you a chance to see America’s hidden gems.
From £1885pp

What's Included

  • Flights from Dublin to Chicago and return from Los Angeles
  • 15 NIGHTS accommodation in selected Fly Drive hotels
  • Compact Car Rental with fully inclusive insurance
  • 2018 Departure Dates: Departs daily from April - Oct 2018
  • Quote Ref 1531803

Staff Tips

Chicago-Bike past giant red and pink painted steel horses or stroll by an apple rocket in stainless steel and bronze at the Skokie Northshore Sculpture Park, which combines original contemporary sculpture and two miles (3.2 kilometers) of walkways—all for free.

Claire Somers

Travel Expert

Chicago-Head to the underwater viewing area to catch a glimpse of swimming sea lions or take a guided tour of the hundreds of species on view at the Lincoln Park Zoo. Admission to the zoo is free seven days a week.

Jennifer Mulligan

Travel Expert

Los Angeles-Hollywood’s Forever Cemetery is the resting place of the ‘Rock n Roll’ faithful. During the Summer months outdoor movies are screened at night.

Sarah McCormick

Travel Expert

Your Adventure...

Chicago Arrival
Chicago - St. Louis (480KM)
St. Louis - Springfield (340KM)
Springfield – Tulsa – Oklahoma City (520KM)
Oklahoma City – Amarillo (420KM)
Amarillo - Albuquerque (450KM)
Albuquerque – Santa Fe – Albuquerque (186KM)
Albuquerque – Holbrook (420KM)
Holbrook – Grand Canyon National Park/ Williams (290KM)
Grand Canyon National Park / Williams – Las Vegas (480KM)
Las Vegas
Las Vegas – Santa Monica/Los Angeles
Los Angeles/Santa Monica
Los Angeles
  • Day 1 Chicago Arrival

    Arrive at the airport and transfer independently to your hotel.

  • 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 travelers. Stroll the lakefront, peruse the shops, bike the parks, grab a Chicago Dog, or explore the city’s incredible sights and architectural treasures including Willis Tower, North America's tallest building.

  • Day 3 Chicago - St. Louis (480KM)

    This morning, pick up your rental car and get ready for an unforgettable journey historic Route 66. This legendary old road passes through a variety of pure Americana landscapes and takes in some of the country’s biggest, oldest and most peculiar sites. En route, don’t miss Wilmington’s most photographed “citizen”, the larger-than-life green Gemini Giant, and Atlanta’s Bunyan Giant, a 19-foot statue of Paul Bunyan holding a giant hot dog. In Springfield, stop at 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, the largest city along Route 66, follow in the footsteps of legendary explorers by visiting the historic sites found throughout the city, including the Gateway Arch, the nation’s tallest monument.

  • Day 4 St. Louis - Springfield (340KM)

    Continue through the Ozark Highlands of southern Missouri to Springfield, recognized as the birthplace of Route 66 in 1926. En route, be sure to stop at Meramec Caverns, Missouri’s buried treasure located in Stanton. These caverns are an extensive set of natural limestone caves whose formations and colors are as unique as they are beautiful. Adding to the pleasure of exploring the caves is learning that Jesse James used them as a hideout and took advantage of the underground river to escape through the “back door”.

  • Day 5 Springfield – Tulsa – Oklahoma City (520KM)

    This morning, cut through the southeastern corner of Kansas, the shortest stretch of Route 66’s eight-state run, on your way to Oklahoma City. The Oklahoma section of Route 66 contains more drivable miles than any other state as well as several miles of the original 9-foot road segment that served Oklahoman families headed west in search of better opportunities during the 1930’s. En route to Oklahoma City, stop to view the beloved 20-foot tall cement Blue Whale in Catoosa, a landmark along Route 66, and the Cyrus Avery Route 66 Memorial Bridge in Tulsa, honoring the “Father of Route 66’s” memory and connection to the historic highway. Once in Oklahoma City, the state’s capital, be sure to check out the old Route 66 motels, gas stations and numerous vintage buildings.

  • Day 6 Oklahoma City – Amarillo (420KM)

    Continue through Oklahoma to Amarillo, located in the pancake-flat plains of the Texas Panhandle. This area of Texas was once the buffalo-rich grasslands of the Great Plains, inhabited by bands of Kiowa and Comanche Indians. Stop en route at the Route 66 Museum in Clinton where you can experience six decades of Route 66 history, and at Shamrock’s Tower Station and U-Drop Inn Café, whose towering spire is still a reminder of the booming business it once saw. See the first restored Phillips 66 gas station in McLean, and two other eye-catching sights in Groom, the leaning water tower and a giant stainless steel cross that easily stands 150-feet tall. In Amarillo be sure to stop at Big Texas Steak Ranch where only the very hungry should attempt their 72oz. steak challenge.

  • Day 7 Amarillo - Albuquerque (450KM)

    Before leaving Amarillo be sure to visit Cadillac Ranch. Meant to represent the “Golden Age” of American-made automobiles, this unique display of art features a row of ten colorfully painted Cadillac cars buried grille first in the ground. Continue to the MidPoint Café in Adrian, ideally located at the halfway point of Route 66 and famous for its “ugly crust” pies. From Adrian you’ll follow Route 66 to Albuquerque, New Mexico for a great taste of the Land of Enchantment.

  • Day 8 Albuquerque

    Located approximately in the center 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 Downtown Albuquerque’s Central Avenue, a treasure trove of Route 66 landmarks and one of the original Route 66 towns. Historic Old Town offers a taste of New Mexico’s Spanish colonial past while the Indian Pueblo Cultural Center, owned by the state’s 19 different Pueblo communities, traces the history of the region’s Native American cultures.

  • Day 9 Albuquerque – Santa Fe – Albuquerque (186KM)

    To get a true sense of the Old Route 66, today you will detour to New Mexico’s state capital, Santa Fe. Founded on the ruins of an abandoned Indian village and steeped in history, Santa Fe is the oldest Capital in the U.S., and although it lost its place on Route 66 in 1938, it remains one of the most picturesque cities in the state. At one time this was the end of the old Santa Fe Trail, the earliest trade route linking the American frontier back east with the far west. Plan to visit one of Santa Fe’s famous art galleries, art markets, or museums full of traditional and contemporary art, including works by their own Georgia O’Keeffe, or shop for authentic creations you just won’t find anywhere else.

  • Day 10 Albuquerque – Holbrook (420KM)

    This morning, the state of Arizona welcomes Route 66 travelers with an overwhelming display of trading posts. View huge concrete tepees that stand at the foot of brilliant red-rock mesas en route to Petrified Forest National Park, the only park in the National Park System containing a section of Historic Route 66. Here you will come face-to-face with over 13,000 years of human history and one of the world’s largest and most colorful assemblies of petrified wood, historic structures and archeological sites. Catch a sunset over the Painted Desert from the park’s Kachina Point before heading to Holbrook. Once in Holbrook, stop at the Wigwam Motel whose steel and concrete teepees featuring modern conveniences have welcomed guests since the 1950’s.

  • Day 11 Holbrook – Grand Canyon National Park/ Williams (290KM)

    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, a natural wonder that you simply have to see to believe. 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 along the historic Hermit Road. Visit a Photo Hot Spot, or climb to the top of a stone Watchtower for panoramic views that extend over 100 miles on clear days.

  • Day 12 Grand Canyon National Park / Williams – Las Vegas (480KM)

    Leave the pretty town of Williams and the Grand Canyon behind 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, to one of Arizona’s hidden treasures, Hoover Dam. Considered the largest single public works project in the history of the U.S., The Hoover Dam straddles the mighty Colorado River, which forms the border between Nevada and Arizona and brings much-needed water and power to the Southwest. Continue to Las Vegas, Nevada, a city that needs no introduction.

  • Day 13 Las Vegas

    Enjoy a full day Las Vegas style. Walk the famous Las Vegas Strip lined with 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 – Santa Monica/Los Angeles

    This morning, set out through the Mojave Desert for Calico Ghost Town, Yermo, California’s authentic silver mining town and one of the few original mining camps of the Old West. Rejoin Route 66 in Barstow where a collection of historic photographs and artifacts related to Route 66 and the Mojave Desert Communities are on display at the Route 66 “Mother Road” Museum. Continue through Pasadena, Los Angeles, West Hollywood and Beverly Hills to Santa Monica for a true Hollywood ending to your cross-country journey. Park and venture the last few blocks on foot to view the “End of the Trail” sign on Santa Monica’s Pier. This sign officially marks the western end of historic Route 66.

  • Day 15 Los Angeles/Santa Monica

    Spend the day strolling along the beaches of Santa Monica or browsing the adjacent indoor/outdoor shops at Third Street Promenade. Or, further explore L.A.’s one-of-a-kind destinations, playgrounds of the rich and famous and architectural gems. Universal Studios Hollywood and Anaheim’s original Disneyland Park are also located within easy driving distance.

  • Day 16 Los Angeles

    Return your rental car at Los Angeles International Airport prior to your departure
    Please note: One way drop off fee on your car rental applies locally and is approx $500

More Great Holiday Deals...

  • From

    Canyon Adventure Fly Drive

    This vacation combines the fast-paced fun of Las Vegas with the natural beauty of the nearby national parks, valleys,...
    • More Detail
  • From

    Golden California Fly Drive

    This fly drive holiday down California’s famous Pacific Coast Highway on State Route 1 promises breath-taking scene...
    • More Detail
  • From

    Pacific Coast Fly Drive

    Like the freedom of driving and stopping off where and when you please..this one is for you!
    • More Detail


By Ali McCurdy

Best Boutiques in LA

By Adrienne Keogh

What to do in Chicago in One Day

By Adrienne Keogh

Best Brunches in NYC