Day 1
Chicago
Welcome to Chicago! Upon arrival at Chicago O'Hare International Airport, transfer independently to the hotel your own way to the hotel. Meet your Tour Director and enjoy an evening in Chicago at your leisure.
Overnight: The Whitehall Hotel, BW Premier Collection or similar
Day 2
Chicago
Set out on a guided morning tour to discover Chicago’s legendary skyline, featuring masterworks by Mies van der Rohe, Frank Lloyd Wright, and Daniel Burnham. You’ll experience the energy of the Magnificent Mile and visit Navy Pier, a historic naval site transformed into a premier entertainment destination. Wander through the lush greenery of Grant and Lincoln Parks and snap a photo at the iconic Cloud Gate sculpture. The afternoon is yours to explore, or you can enhance your stay by booking a visit to the Willis Tower, a scenic river cruise, or an elegant dinner cruise through your Tour Director.
Overnight: The Whitehall Hotel, BW Premier Collection or similar. Breakfast included.
Day 3
Chicago to St Louis (approx.. 300 miles)
Bid farewell to the Windy City as your journey down Historic Route 66 officially begins. This legendary highway winds through a tapestry of pure Americana, featuring a quirky collection of the country's most iconic and unusual landmarks. Following the traditional eastbound-to-westbound path, you’ll travel from Chicago toward St. Louis, Missouri, passing through a scenic landscape of golden cornfields and vast, flat prairies. Upon arrival in St. Louis – a cornerstone city of the Mother Road – you can walk in the footsteps of explorers like Lewis and Clark at the Gateway Arch. Standing as the nation’s tallest monument within a National Park, it serves as a majestic "Gate to the West."
Overnight: Pear Tree Inn St. Louis Convention Center, Courtyard St Louis Downtown West or similiar. Breakfast included.
Day 4
St. Louis to Springfield (approx.. 220 miles)
Your journey continues through the scenic Ozark Highlands of Southern Missouri, the region famously recognized as the birthplace of Route 66. Along the way, you’ll stop at Meramec Caverns, a breathtaking limestone cave system renowned for its vibrant colours and unique geological formations. The experience is made even more legendary by the history hidden within; learn how the notorious outlaw Jesse James used these caverns as a secret hideout, utilizing the underground river to make his daring escapes through the "Back Door."
Overnight: Holiday Inn & Suites Springfield - I-44 or similar. Breakfast included.
Day 5
Springfield to Tulsa and onwards to Oklahoma City (approx.. 286 miles)
This morning you’ll clip the southeastern corner of Kansas as you head into Oklahoma, the state boasting the longest driveable stretch of the Mother Road. This path carries deep history, as it was once the primary route for thousands of families seeking a new life during the 1930s. Along the way, you’ll spot the whimsical Blue Whale of Catoosa, one of the route’s most beloved landmarks. Upon reaching Tulsa, you will see the Cyrus Avery Route 66 Memorial Bridge; though now a silent monument listed on the National Register of Historic Places, it remains a powerful symbol of the "East meets West" spirit. Your day concludes in Oklahoma City with a brief orientation tour of the vibrant state capital.
Overnight: Springhill Suites Oklahoma City Downtown or similar. Breakfast included.
Day 6
Oklahoma City to Amarillo (approx.. 260 miles)
Your journey continues toward Amarillo, nestled within the vast, level plains of the Texas Panhandle. This region, once a sea of buffalo-rich grasslands, served as the ancestral home of the Kiowa and Comanche people. Along the way, immerse yourself in six decades of "Mother Road" nostalgia at the Oklahoma Route 66 Museum in Clinton (admission included). As you cross into Texas, enjoy a photo stop in Shamrock to see the iconic U-Drop Inn and Tower Station, a masterpiece of Art Deco architecture. You’ll also visit a beautifully restored 1929 Phillips 66 station in McLean – a reminder of the era when the boom in cross-country travel led oil companies to dot the highway with these now-historic service stations.
Overnight: Comfort Inn & Suites Amarillo. Breakfast included.
Day 7
Amarillo to Albuquerque (approx.. 290 miles)
Before departing Amarillo, a visit to the world-renowned Cadillac Ranch is an absolute must. This iconic public art installation features ten vibrantly painted Cadillacs, buried nose-first in the soil since 1974. Representing the evolution of the car's tailfin from 1949 to 1963, this landmark now draws over one million visitors annually. From there, your journey continues west across the state line into New Mexico toward Albuquerque. As the state’s largest city, Albuquerque serves as a thriving hub for technology and the arts, and is famously home to the spectacular International Balloon Fiesta.
Overnight: Best Western Plus RIO Grande Inn Albuquerque. Breakfast included.
Day 8
Albuquerque to Gallup and onto Holbrook (approx.. 230 miles)
Depart Albuquerque and head north to Gallup, a quintessential Route 66 community that feels frozen in the highway’s golden era. This city offers a rare slice of authentic Americana, featuring one of the most vibrant stretches of vintage neon signs found anywhere on the Mother Road. Take some time to browse unique Southwestern gift stores before crossing into the Navajo Nation. As the largest Native American reservation in the United States, it spans over 17 million acres across Arizona, New Mexico, and Utah. During the afternoon, you have the opportunity to join an optional excursion to Canyon de Chelly, where ancient Puebloan ruins and historic pictographs offer a profound introduction to Navajo heritage and culture.
Overnight: Best Western Arizonian Inn or similar. Breakfast included.
Day 9
Holbrook to Monument Valley and onto Page (approx.. 210 miles)
Depart Holbrook and continue your expedition through the heart of the Navajo Nation toward the iconic Monument Valley. Prepare to be mesmerized by a landscape of towering mesas, dramatic buttes, and ancient stone monuments that define the American West. This world-famous backdrop has starred in countless movie classics. To truly immerse yourself in this sacred land, join an optional Jeep tour for an up-close look at the valley's most famous formations before heading to Page, Arizona, for the night.
Overnight: Best Western Plus Lake Powell or similar. Breakfast included.
Day 10
Page to the Grand Canyon and Williams (approx.. 165 miles)
Before departing Page, don’t miss the chance to join an optional excursion to Antelope Canyon. As the most photographed slot canyon in the American Southwest, its winding pathways and smooth sandstone walls were carved over millennia by the powerful forces of wind and water. From there, journey back through the Navajo Nation to the awe-inspiring Grand Canyon. Established as a National Park in 1919, this natural wonder draws nearly five million visitors each year. Your day concludes in the historic Route 66 town of Williams, where you’ll board the Grand Canyon Railway for an unforgettable train journey (included) through the heart of the park's magnificent landscapes.
Overnight: Grand Canyon Railway Hotel or similar. Breakfast included.
Day 11
Williams to Kingman and onto Las Vegas (approx.. 220 miles)
Depart Williams and transition from I-40 onto a preserved stretch of the Mother Road to visit Seligman, Arizona. This town is the heart of the route’s revival; it was here that residents successfully lobbied to designate the highway as "Historic Route 66" in 1987. Today, Seligman remains a vibrant time capsule where friendly locals warmly welcome travellers year-round. Continue through Kingman and leave the desert quiet behind for the dazzling energy of Las Vegas. Known as the "Entertainment Capital of the World," the city is famous for its 24-hour excitement, spectacular shows, and iconic mega-resorts. This evening, join your fellow travellers for an optional orientation tour to explore the sights and sounds of the world-famous Strip.
Overnight: Luxor Las Vegas, Excalibur or similar. Breakfast included.
Day 12
Las Vegas
Enjoy a full day at your leisure to experience the endless excitement of Las Vegas at your own pace. Whether you choose to relax by the pool or explore the themed resorts, your Tour Director is available to help you make the most of your stay. You may also join one of our curated optional excursions, such as a morning visit to the historic Hoover Dam or an evening Dinner and Show program for a quintessential Vegas experience.
Overnight: Luxor Las Vegas, Excalibur or similar. Breakfast included.
Day 13
Las Vegas to Los Angeles ( approx.. 270 miles)
After a relaxing morning, you’ll make a final stop at the world-famous "Welcome to Las Vegas" sign for a classic photo opportunity before departing. Your journey then takes you across the vast Mojave Desert and into California toward Barstow and Yermo. Step back in time with a visit to Calico Ghost Town (admission included), a 19th-century silver mining hub that was later rescued and restored to its peak-era glory by the founders of Knott’s Berry Farm. After reliving the rugged days of the Old West, you’ll continue westwards, arriving in the sprawling metropolis of Los Angeles in the afternoon.
Overnight: Luxor Las Vegas, Excalibur or similar. Breakfast included.
Day 14
Los Angeles
Experience the magic of this sprawling metropolis with a full-day city tour. You’ll explore Los Angeles’ most famous neighbourhoods, from the historic architecture of Downtown LA to the star-studded Hollywood Walk of Fame. After a stop at the bustling Farmers Market and The Grove, we’ll cruise through the palm-lined streets of Beverly Hills on our way to the coast. Our journey concludes at Santa Monica, the official end of the Mother Road. Enjoy some free time to explore the beach and the historic Santa Monica Pier, home to the iconic "End of Route 66" sign. Finally, celebrate your cross-country adventure with an included farewell dinner before the tour concludes at the LAX hotel.
Overnight : Sonesta Los Angeles Airport LAX or similar. Breakfast included.
Day 15
Departure. Breakfast included.
