Your Itinerary
Day 1 - Centennial Route 66 - Arrival
After arriving at Chicago O'Hare International Airport, make your own way to the hotel.
Your tour leader will be available to greet you at the Hospitality/Welcome Desk between 2:00 pm and 8:00 pm. The remainder of the day is at your leisure.
Special InformationAirport transfers are not included. Our transfer portal may offer the option to book your airport transfers for an easier arrival experience (additional charges apply). Access to this portal will be available through your Traveller Hub once your booking is confirmed.
Day 2 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
Following breakfast, enjoy a morning city tour of Chicago featuring impressive modern architecture by famous architects such as Mies van der Rohe, Frank Lloyd Wright, and Daniel Burnham. Visit highlights including the Magnificent Mile, Navy Pier, Grant and Lincoln Parks, and the iconic Cloud Gate sculpture.
The afternoon is at leisure, giving you time to explore independently or join optional experiences such as a visit to Willis Tower or a river cruise, subject to availability. Your tour leader will be happy to provide personalised recommendations.
Inspiring Highlights
Chicago city tour
Magnificent Mile
Day 3 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
Say goodbye to Chicago as you set off on the legendary Historic Route 66, one of America's most iconic highways. Travel through classic Americana landscapes of rolling cornfields and wide open prairies, discovering charming roadside attractions and timeless scenery along the way. Follow the traditional east to west route toward St. Louis, Missouri, a vibrant city rich in history and culture. Upon arrival, marvel at the spectacular Gateway Arch, the nation's tallest monument and a powerful symbol of westward expansion, set within a beautiful National Park and honouring famous explorers such as Lewis and Clark.
Inspiring Highlights
Commence Historic Route 66
Gateway Arch
Day 4 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
Continue your journey through the scenic Ozark Highlands of southern Missouri, known as the birthplace of Route 66.
Along the way, visit the spectacular Meramec Caverns, a natural limestone cave filled with stunning formations and vibrant colors. As you explore this underground wonder, discover its fascinating history as a former hideout of the infamous outlaw Jesse James, who once used the hidden river passage as an escape route known as the “Back Door.”
Inspiring Highlights
Ozark Highlands
Meramec Caverns
Day 5 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
This morning, travel through the south-eastern corner of Kansas as you continue toward Oklahoma City. The Oklahoma stretch of Route 66 features more drivable miles than any other state and carries deep historical significance, as many families journeyed west along this road during the 1930s in search of new opportunities.
Along the way, see the famous Blue Whale of Catoosa, one of Route 66's most beloved landmarks.
In Tulsa, pass the historic Avery Route 66 Memorial Bridge, built in 1915 and later recognized on the National Register of Historic Places. Upon arrival in Oklahoma City, enjoy a brief orientation tour of the state capital.
Inspiring Highlights
Blue Whale of Catoosa
Avery Route 66 Memorial Bridge
Day 6 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
Travel onward to Amarillo, set among the wide open plains of the Texas Panhandle. This region was once part of the vast buffalo grasslands of the Great Plains and home to the Kiowa and Comanche Native American tribes. Along the way, visit the Oklahoma Route 66 Museum in Clinton, where you will explore six decades of Route 66 history (admission included).
Continue to Shamrock, Texas, famous for the iconic Conoco Tower Station and U Drop Inn Café, followed by a photo stop in McLean at the beautifully restored Phillips 66 gas station, originally opened in 1929. These classic service stations reflect the rise of automobile travel and the growing demand for fuel along Route 66.
Inspiring Highlights
Oklahoma Route 66 Museum
Conoco Tower Station and U Drop Inn Cafe in Shamrock
Phillips 66 Gas Station
Day 7 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
Before departing Amarillo, stop at the world famous Cadillac Ranch, a striking outdoor art installation featuring ten brightly painted Cadillac cars buried nose first in the ground since 1974. Spanning models from 1949 to 1963, this iconic landmark attracts over one million visitors each year.
Continue west into the neighboring state of New Mexico, arriving in Albuquerque. As the state's largest city, Albuquerque is a vibrant center for technology, arts, and culture, and is especially famous for hosting the annual International Balloon Festival.
Inspiring Highlights
Cadillac Ranch
Day 8 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
We depart Albuquerque this morning and travel north along historic Route 66 to Gallup, a classic town known for its nostalgic Americana feel and glowing neon signs. Enjoy free time to explore and browse Southwestern gift shops before continuing into the vast Navajo Nation, which spans Arizona, New Mexico and Utah.
This afternoon, there is an optional excursion to Canyon de Chelly, where dramatic sandstone cliffs frame ancient pueblos and centuries old rock art, offering a deeper understanding of Navajo history and culture.
Inspiring Highlights
Historic Gallup
Navajo Nation reserve
Canyon de Chelly
Day 9 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
After breakfast, we leave Holbrook and journey across the Navajo Nation to the iconic landscapes of Monument Valley. Admire the striking sandstone formations, towering mesas, and dramatic buttes that have made this region famous in countless films, from classic westerns to modern favourites like Forrest Gump and Back to the Future.
For an even closer experience, an optional jeep tour offers the chance to explore the valley's remarkable scenery up close.
Inspiring Highlights
Monument Valley
Day 10 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
This morning we travel to the spectacular Grand Canyon, one of the world's most extraordinary natural wonders and a designated National Park since 1919. Marvel at the immense scale, layered rock formations and sweeping vistas carved over millions of years.
In the mid afternoon, board the historic Grand Canyon Railway for a scenic journey through the landscapes of Grand Canyon National Park to the town of Williams.
Later, arrive in Williams, a character filled Route 66 community known for its vintage charm, classic diners and nostalgic Americana atmosphere.
Inspiring Highlights
Grand Canyon
Grand Canyon Railway
Day 11 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
After breakfast, we depart Williams and travel along Interstate 40 before rejoining Historic Route 66 on our way to Seligman, Arizona. This character filled town played a pivotal role in preserving Route 66, helping secure its designation as Historic Route 66 in 1987. We'll have time to explore and experience the warm hospitality of this enduring roadside community.
We continue through Kingman toward the bright lights of Las Vegas, where elaborate resort hotels line the legendary Strip. Widely known as the Entertainment Capital of the World, Las Vegas is famed for its casinos, world class shows and vibrant nightlife. This evening, we have the option to join an orientation tour, combining walking and driving, to discover some of the Strip's most iconic hotels and landmarks.
Inspiring Highlights
Las Vegas Strip
Day 12 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
Today enjoy a full day at leisure to experience Las Vegas at our own pace. Stroll along the Strip and explore the themed resort hotels, visit Fremont Street for its lively atmosphere and light shows, or relax by the pool. For panoramic views, head up the High Roller Observation Wheel or the STRAT Tower.
Last minute tickets are often available for headline shows, concerts and Cirque du Soleil performances, or you may wish to book a dinner experience at one of the city's renowned restaurants. Alternatively, speak with your tour leader about optional excursions such as a visit to the Hoover Dam.
Day 13 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
After a relaxed morning in Las Vegas, stop for photos at the iconic “Welcome to Las Vegas” sign before continuing through the Mojave Desert into California toward Barstow and Yermo.
Upon arrival, visit Calico Ghost Town (admission included), a restored 19th century mining town that once thrived during the silver rush before being carefully rebuilt to reflect its historic peak. Step back in time and experience the spirit of the Old West.
In the afternoon, we arrive in Los Angeles, a vast and vibrant metropolis home to more than 18 million residents.
Inspiring Highlights
Welcome To Las Vegas sign
Calico Ghost Town
Day 14 - 15 Day Centennial Route 66 - Chicago to Los Angeles - Current
Enjoy a full day city tour of Los Angeles, exploring many of the famous districts that make the city so iconic. Visit downtown Los Angeles, Hollywood and the Walk of Fame, the lively Farmers Market and The Grove, and pass through glamorous Beverly Hills before reaching the official end of Route 66 in Santa Monica. Here, enjoy free time to stroll along the beach and visit the Santa Monica Pier, home to the famous “End of Route 66” sign.
After a special farewell dinner, your Historic Route 66 journey concludes with arrival at your LAX Airport hotel.
Inspiring Highlights
Downtown Los Angeles
Hollywood and the Walk of Fame
Farmers Markets and The Grove
Beverley Hills
End of Route 66 sign in Santa Monica
Special farewell dinner
Day 15 - Departure - Centennial Route 66
After breakfast, check out of your hotel and make your own way to Los Angeles International Airport for your onward journey. Depart with unforgettable memories of your Historic Route 66 adventure.
Thank you for travelling with Inspiring Vacations. We hope you had a memorable experience.
Special Information
Airport transfers are not included. Our transfer portal offers the option to book your airport transfers for an easier arrival experience (additional charges apply). Access to this portal will be available through your Traveller Hub once your booking is confirmed.
