Arrive into O’Hare International Airport, Chicago, collect your bags and transfer independently to your centrally located hotel.

Chicago is a city with a rich history and a musical soul. From the towering skyline to the smokey lounges where you can hear jazz and blues, Chicago offers a special treat for anyone with a special interest.

Gale Chicago or similar

Begin your day by standing on the corner of Michigan and Adams, marked as the starting point of Historic Route 66. Perhaps enjoy coffee and a big breakfast at Lou Mitchell’s, a Chicago institution since 1923 and a must for Route 66 travellers.

Walk to Millennium Park, where you can grab a selfie next to the iconic Cloud Gate sculpture (commonly known as “The Bean”) and then stroll through the serene Lurie Garden.

You could then stroll across to nearby Grant Park to visit the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Alternatively, head to the nearby Loop neighborhood and take a ride on the Chicago Architecture Foundation River Cruise. On the boat you learn about the city’s fascinating architectural history as you cruise along the Chicago River, passing by iconic skyscrapers and historic landmarks.

Later, make your way to Navy Pier, a popular entertainment destination right on Lake Michigan. You can take a ride on the Centennial Wheel for panoramic views of the city skyline and Lake Michigan, and enjoy the lakefront atmosphere.

Optional Experience – Inside Chicago Grand Tour

Join this guided tour around Chicago’s best sites ending with a visit to the Hancock Tower, one of the city’s tallest landmarks.

Gale Chicago or similar

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 road passes through a variety of American landscapes and takes in some of the country’s biggest, oldest and more peculiar sites along the way.

Begin your road trip by following the traditional east-to-west path of Route 66 from Chicago to St. Louis, Missouri, cruising through cornfields and flat prairies.

On today’s 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, we recommend stopping at the Cosy Dog Drive-in, the birthplace of the corn dog, and exploring 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.

Chicago > St. Louis | 297 miles

Hampton Inn St. Louis Southwest or similar

Today’s drives continues through the Ozark Highlands of southern Missouri to Springfield, recognised as the birthplace of Route 66.

You may like to make a detour to view the Meramec Caverns, one of the largest and cave systems along Route 66. You can take a guided tour of the caverns to marvel at the impressive limestone formations that became a hideout for the outlaw Jesse James

Be sure to stop in the town of Cuba, known as the “Route 66 Mural City” for its vibrant murals depicting scenes from the road’s heyday. Don’t miss the Wagon Wheel Motel and the restored Route 66 Rocker, iconic landmarks along the route.

Drive through Devil’s Elbow, a scenic stretch of Route 66 known for its winding road and picturesque views of the Big Piney River. You may like to stop at the Elbow Inn Bar & BBQ for a bite to eat and to admire the vintage decor.

We think you will like to spend your evening in Springfield at the Route 66 Car Museum. The museum features a collection of classic cars and memorabilia from the heyday of America’s most famous highway.

St. Louis > Springfield | 216 miles

Best Western Coach House or similar or similar

This morning, cut through the southeastern corner of Kansas 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 segments that served Oklahoman families headed west in search of better opportunities during the 1930s.

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 honouring 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.

Springfield > Oklahoma City | 312 miles

Hilton Garden Inn Oklahoma City North Quail Springs or similar

We recommend starting today to the north of Oklahoma City, at Arcadia, home to the iconic Round Barn. Built in 1898, this historic structure is one of the most photographed landmarks along Route 66. You can still explore the barn’s interior, learn about its history, and browse the gift shop. Just outside of Arcadia, stop at Pops, a popular roadside attraction known for its giant soda bottle sculpture.

Continue 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.

See Shamrock’s Tower Station and the U-Drop Inn Cafe 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 in Groom, the leaning water tower and a 150-foot tall stainless steel cross.

Once in Amarillo, be sure to stop at Big Texas Steak Ranch where you can attempt their 72oz. steak challenge.

Oklahoma City > Amarillo | 295 miles

Hilton Garden Inn Amarillo or similar

Start today with a visit to a modern Route 66 icon. Cadillac Ranch is a unique art installation featuring ten Cadillacs buried nose-first in the ground. Visitors are encouraged to leave their mark by spray painting the cars, making it a colourful and ever-changing work of art..

Continue to the Mid Point Café in Adrian famous for its ‘ugly crust’ pies. From Adrian, follow Route 66 to Santa Rosa, home to the famous Blue Hole, a natural swimming spot with crystal-clear blue waters. You may like to take a refreshing dip or simply stop at the edge to enjoy the scenic beauty of this unique geological feature.

Continue to to the city of Albuquerque where your hotel is waiting for you.

Amarillo > Albuquerque | 270 miles

Ramada Plaza by Wyndham Albuquerque Midtown or similar

The state’s largest city, Albuquerque spreads north and south along the banks of the Rio Grande.

You could spend the day exploring Downtown Albuquerque’s Central Avenue, a treasure trove of Route 66 landmarks. Historic Old Town offers a taste of New Mexico’s Spanish colonial past while the Indian Pueblo Cultural Centre, owned by the state’s 19 different Pueblo communities, traces the history of the region’s Native American cultures. 

We also recommend riding the Sandia Peak Tramway, to enjoy the views from the longest aerial cable car in America. You can simply enjoy the scenery as you ascend to the peak or get off to follow one of the many hiking trails.

Ramada Plaza by Wyndham Albuquerque Midtown or similar

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.

Albuquerque > Santa Fe | 116 miles

Courtyard Santa Fe or similar

This morning, the state of Arizona welcomes Route 66 travellers 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 colourful assemblies of petrified wood, historic structures and archaeological 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 tepees featuring modern conveniences have welcomed guests since the 1950s.

Santa Fe > Holbrook | 260 miles

Quality Inn Holbrook or similar

From Holbrook 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.

Holbrook > Grand Canyon/ Williams | 180 miles

Grand Canyon Railway Hotel or similar

Leave the 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, the Hoover Dam. Considered the largest single public works project in the history of the U.S., 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.

Williams > Las Vegas | 300 miles

Planet Hollywood Resort or similar

Enjoy a full day to immerse yourself in Las Vegas.

Walk the famous 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, and lay by the pool … the list goes on.

With so much to do, 24 hours in a day hardly seems like enough. 

Planet Hollywood Resort or similar

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.

Rejoin Route 66 in Barstow where the ‘Route 66 Mother Road Museum’, showcases the history and culture of America’s most famous highway. Explore exhibits on the road’s heyday, view vintage cars and memorabilia.

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.

Las Vegas > Santa Monica | 290 miles

Le Meridien Delfina, Santa Monica or similar

Los Angeles by the sea, Santa Monica is a seaside town most famous for its pier as well as the fact that it is the end of the historic Route 66.

Santa Monica is very walkable, so you could spend a day out of the car exploring on foot. Wander down to the soft golden sands and walk along the paved promenade, watching the fitness followers and families at play. Walk out onto the historic pier where a variety of amusements and rollercoasters dominate the skyline.

Alternatively, join a sightseeing bus tour to take in the Hollywood studios and the Walk of Fame.

You could choose to go behind the scenes of Paramount Studios or enjoy the fun at Universal Studios also in Hollywood. For the full theme park experience drive to Anaheim to enjoy the rides at Disneyland.

Optional Experience – Hop-on Hop-off Bus Tour
A fun, informative and easy way to explore the wonders of Los Angeles. Stopping by all of the major sights and attractions. Your pass will be valid for 24 hours.

Le Meridien Delfina, Santa Monica or similar

Your epic journey along ‘America’s Mother Road’ comes to an end today. You could choose to stay a little longer in Santa Monica and explore more of Los Angeles, alternatively make your way to Los Angeles International airport in time to return your car, and check-in for your homeward flight.   

Santa Monica > Airport | 12 miles