Step back in time to the golden age of road travel on one of the world’s famous highways, Route 66. Your epic 2000-mile journey will be full of kitsch and quirky Americana.
Suggested route & duration
Suggested duration 18 nights from Chicago
• Chicago, Illinois: 2 nights
• Springfield, Illinois: 1 night
• St Louis, Missouri: 2 nights
• Springfield, Missouri: 1 night
• Tulsa, Oklahoma: 1 night
• Oklahoma City, Oklahoma: 1 night
• Amarillo, Texas: 1 night
• Tucumcari, New Mexico: 1 night
• Albuquerque, New Mexico: 2 nights
• Flagstaff, Arizona: 2 night
• Las Vegas, Nevada: 2 nights
• Santa Monica, California: 2 night
About this independent tour
Why you’ll love this self-drive
• Go on an epic drive across the Mid-West and South West states
• Explore big cities such as Chicago, St Louis and Los Angeles
• Check out the weird and wonderful roadside attractions along the route, like the Blue Whale of Catoosa near Tulsa
When to go
• At over 2000 miles, the route crosses several climate zones but generally
the best driving conditions are between late April and October
• During the height of summer, temperatures in Texas and the South West states can rise to the high 30s or low 40s; the Southwest Monsoon brings heavy rains and thunderstorms to the region
Suggested self-drive details
Day 1: Chicago Explore this lakeside city and make sure you see the Route 66 Begin sign. Stay 2 nights at Raffaello.
Day 3: Springfield (Illinois) Explore the hometown of President Lincoln. Stay at Crowne Plaza Springfield.
Day 4: St Louis See the iconic Gateway Arch in the biggest Route 66 city between Chicago and LA. Stay 2 nights at Holiday Inn Downtown Convention Center.
Day 6: Springfield (Missouri) Discover original parts of the 1930s road and drive past historic motels. Stay at Best Western Rail Haven.
Day 7: Tulsa Pass into the Sooner State and get a picture of the Route 66 Rising sculpture. Stay at Holiday Inn Tulsa City Centre.
Day 8: Oklahoma City Stop for the night in the state capital of Oklahoma and get some comfort food at the historic Cheever’s Café. Stay at Best Western Plus Saddleback Inn.
Day 9: Amarillo Route 66 passes through the north of Texas and you’ll stay a night in heritage-packed Amarillo. Stay at Holiday Inn Express.
Day 10: Albuquerque Cross over the state line into New Mexico and learn about native culture in Albuquerque. Stay 2 nights at Best Western Plus Rio Grande Inn.
Day 12: Flagstaff Spend a couple of days exploring northern Arizona, perhaps taking a detour to the Grand Canyon and the town of Williams. Stay 2 nights at Little America Hotel.
Day 14: Las Vegas Enjoy round-the-clock entertainment in Las Vegas. Stay 2 nights at Tropicana Las Vegas.
Day 16: Santa Monica Finish your incredible journey at Santa Monica Pier. Stay 2 nights at Gateway Hotel Santa Monica.
Anish Kapoor’s Cloud Gate sculpture is an icon of Chicago and known by locals as ‘the bean’
Hall of Fame
Visit the Route 66 Hall of Fame in Pontiac, Illinois which is packed with Mother Road memorabilia
Head out to the edge of Albuquerque and take the Sandia Peak Tramway up into the hills
Watch the sun set over the Pacific Ocean from Santa Monica’s famous pier
Tailor your tour
Make it your own
We’ve crafted this self-drive based on our own experiences and customers’ feedback. It’s fully flexible, so talk to us and we can create your perfect trip.
Where to stay
Away from the big cities, you’ll stay in simple chain hotels but as this trip is all about the drive, they’ll just be a place to spend the night. We’ve picked a couple of gems along the way, such as the Little America Hotel in Flagstaff. You can upgrade your hotels in Chicago, Las Vegas and Santa Monica.
Driving Route 66 is all about finding cool and quirky Americana along the way. You’ll have to leave the Interstates to find some of the best places like Pontiac in Illinois, where murals line the main street, the U-Drop Inn in Shamrock, Texas and the iconic Cadillac Ranch.
This is a long drive so two and a half weeks should be the minimum duration. We’ve added two-night stays in cities along the route so you don’t have to spend day after day behind the wheel. A couple more nights in Chicago or Santa Monica is also recommended.
This trip has plenty of stops but you can add stays in other towns and cities on the way. Between Vegas and Santa Monica, take a slight detour to Palm Springs for some resort relaxation in the desert. To relax after, head to Hawaii or return home via Florida’s Gulf Coast beaches.