Experiences
Route 66 road trip: Chicago to Santa Monica
Neon signs, motels and diner coffee across eight states. How to drive Route 66, what to stop for and where to stay along the way.
The diner coffee is weak and topped up before you ask. Outside, a 1950s neon sign flickers, and in the car park sits a rusty pickup nobody has moved for decades. Route 66 is not the fastest way west, but it is the one with the most stories.
Route 66 opened in 1926 and ran from Chicago to Santa Monica, around 2,400 miles through eight states. It was removed from the US highway system in 1985, but much of it can still be driven, and the motels, petrol stations and museums along the way live on.
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How to do it
Allow at least two weeks. Three weeks gives you time for detours to the Grand Canyon and Santa Fe.
Hire a car in Chicago and drop it in Los Angeles. Expect a one-way fee.
Follow the brown Historic Route 66 signs. A dedicated Route 66 guidebook or app makes the old sections easier to find.
Drive westbound if you can, so you finish at the Pacific.
The best stops along the way
Chicago, Illinois: start at the Begin Route 66 sign downtown.
St. Louis, Missouri: the Gateway Arch and the old Chain of Rocks Bridge over the Mississippi.
Oklahoma and Texas: interwar petrol stations and Cadillac Ranch outside Amarillo, where cars stand nose-down in the dirt.
New Mexico: Santa Fe and Albuquerque, with adobe buildings, chilli and red mountains.
Arizona: Petrified Forest, Winslow, Flagstaff, Seligman and the burros of the old mining town of Oatman.
California: the Mojave Desert and the end-of-the-trail sign on Santa Monica Pier.
The long road
Much of Route 66 can still be driven. Photo: Rocio Abrego / Unsplash
How to get the most out of Route 66
Eat where the locals eat. Diners, barbecue joints and small cafés tell you more about the road than the chains by the interstate. Spend at least one night in a proper Route 66 motel with a neon sign, and mix it with better hotels in the cities.
Treat the stretch between Flagstaff and Las Vegas as a chance for detours: the Grand Canyon lies north of Williams, and Las Vegas is only a couple of hours from Kingman.
Book experiences: See tours and activities in Chicago
Book experiences: See tours and activities in Los Angeles
Where to stay along Route 66
Mix simple motels along the way with a few good hotels where you stay several nights.
Palmer House
A historic Chicago hotel where the trip begins. Photo: Hotels.com (Expedia Group)
Palmer House: start in style in Chicago
Palmer House a Hilton Hotel is in the Loop, a short walk from the Route 66 start sign and Grant Park. It is one of Chicago's classic historic hotels, a fine place to gather yourself before the long drive.
Book your stay: See rooms at Palmer House a Hilton Hotel
La Fonda on the Plaza
Adobe and art on the plaza in Santa Fe. Photo: Hotels.com (Expedia Group)
La Fonda on the Plaza: adobe in Santa Fe
La Fonda sits on the plaza in Santa Fe, which lay on the earliest alignment of Route 66. The hotel is full of art, with a restaurant and bar, and the old town is right outside.
Book your stay: See rooms at La Fonda on the Plaza
Little America Flagstaff: rest before the Grand Canyon
Flagstaff sits in the middle of Route 66 in Arizona and is the gateway to the Grand Canyon. Little America is in pine forest on the edge of town, with plenty of space after hours in the car.
Book your stay: See rooms at Little America Flagstaff
Fairmont Miramar: the finish line in Santa Monica
Fairmont Miramar is in Santa Monica, within walking distance of the pier where Route 66 ends. A spa and pool are a fine reward after thousands of miles.
Book your stay: See rooms at Fairmont Miramar Bungalows
When is the best time to drive Route 66?
May, June, September and October are best. You avoid the worst of the summer desert heat and the winter snow at altitude around Flagstaff. July and August are hot, especially in the Mojave.
When should you book?
One-way car hire: several months ahead.
Hotels in Chicago and Santa Monica: a few months ahead.
Motels along the way: a few days ahead, or on the day outside peak season.
Frequently asked questions about Route 66
Where should I stay on Route 66?
Stay at Palmer House in Chicago before you set off and at Fairmont Miramar in Santa Monica at the finish. Along the way, La Fonda in Santa Fe and Little America in Flagstaff are good stops, mixed with classic motels.
How long is Route 66?
Route 66 is around 2,400 miles from Chicago to Santa Monica, through eight states.
How long does it take to drive Route 66?
Allow at least two weeks. Three weeks gives time for detours such as the Grand Canyon, Santa Fe and Las Vegas.
Can you still drive the whole of Route 66?
Much of the old road can still be driven, but some sections have gone or been replaced by interstate. Follow the Historic Route 66 signs and use a dedicated guidebook or app.
Which direction should you drive Route 66?
Most people drive west from Chicago to Santa Monica, so the trip ends at the Pacific and the most dramatic landscapes come towards the end.