Historic Route 66

Trip Itinerary

Day 1

Chicago Arrival

Arrive at Chicago’s O’Hare International Airport and transfer independently to your hotel.

Day 2


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 Americas tallest building.

Day 3

Chicago – St. Louis / driving distance: 300 mi / 480 km

This morning, pick up your rental car and get ready for an unforgettable journey into the then and now of America along 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 along the way. Begin your journey by following the traditional east-to-west path of Route 66 from Chicago to St. Louis, Missouri, cruising through endless cornfields and flat prairies. 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, you can 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 / driving distance: 210 mi / 340 km

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 / driving distance: 310 mi / 520 km

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 driveable 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 / driving distance: 260 mi / 420 km

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 / driving distance: 270 mi / 450 km

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


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 / driving distance: 116 mi / 186 km

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 / driving distance: 260 mi / 420 km

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 / driving distance: 180 mi / 290 km

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 / driving distance: 300 mi / 480 km

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 / driving distance: 290 mi / 470 km

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 Departure

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

Prices, Dates, Hotels & Conditions


‎€ ‎£ $ A$ ¥ C$

The final price you will pay for this tour is that displayed in USD. Prices converted in other
currencies are for guidance purposes only and are approximate.

April, May, June, July, August, September, October 982 1201

1-2 Chicago Holiday Inn Hotel & Suites Chicago Downtown The Whitehall Chicago
3 St. Louis Red Roof Plus St. Louis Omni Majestic Hotel
4 Springfield Best Western Route 66 Rail Best Western Route 66 Rail
5 Oklahoma City Howard Johnson Inn Howard Johnson Inn
6 Amarillo Quality Inn Quality Inn
7-9 Albuquerque Best Western Plus Rio Grande Inn Best Western Plus Rio Grande Inn
10 Holbrook Magnuson Adobe Inn Magnuson Adobe Inn
11 Grand Canyon/Williams Ramada Williams Holiday Inn Express & Suites Grand Canyon
12-13 Las Vegas Excalibur Hotel & Casino Luxor Hotel & Casino
14-15 Los Angeles Quality Inn & Suites Anaheim Resort Hilton Anaheim

- Gaze at Chicago’s Willis Tower, the tallest building in North America
- Take a nostalgic ride along historic Route 66
- Get a bird’s eye view of the Gateway Arch in St. Louis
- Lose yourself in the quiet beauty of Missouri’s Ozark Region
- Experience the nation’s longest drivable stretch of Route 66 in Oklahoma
- Pay a visit to Amarillo’s Cadillac Ranch, a ritual site on The Mother Road
- Sample rich culture and the true Southwest in Albuquerque
- Visit Santa Fe, a UNESCO designated City of Design, Crafts and Folk Art
- Explore one of the best remnants of native Arizona grassland in Petrified Forest
- View one of the 7 natural wonders of the world, the Grand Canyon
- Pay a visit to Hoover Dam
- Enjoy 24 Hour entertainment in glittering Las Vegas
- Explore Calico Ghost Town
- See the replica of the long-lost Route 66 “End of the Trail” sign at the Santa Monica Pier
- Get closer to the stars at Grauman’s Chinese Theater, a Hollywood landmark
- Commemorative certificate of having driven Historic Route 66
Admission fees not included

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