(Updated itinerary: 29th April 2024)
Drive Route 66 from Chicago to Los Angeles with some great side trips thrown in.
This self drive holiday takes you along Route 66 at a very manageable pace. You’ll have enough time in Chicago to see the main sites before embarking on your approx 2500 mile journey to Santa Monica in California. You’ll also enjoy side trips to the absolutely breathtaking Monument Valley, Grand Canyon and Las Vegas.
The hotels, motels and inns are hand-picked to give value for money, but also great quality in ideal locations. We use a mix of well known brands and independents, some will be in downtown areas, others right on Route 66 and will be a variety of modern and historic. However all will be absolutely perfect for your trip.
You’ll stay just steps away from Magnificent Mile in Chicago, overlooking the Gateway Arch in St Louis, actually inside Monument Valley, near the south entrance to the Grand Canyon and right in the middle of the Las Vegas Strip. Of course, if you have any preferred hotels, please let us know.
You’ll receive a full road trip pack with information on to stay on Route 66, how to make the most of your trip, information on roadside attraction and trivia. We’ll also give you some useful recommendations for cafes, restaurants and things to do along the way.
Remember - All our holidays can be shortened or extra nights added or modified with upgraded hotels, car etc. We love building tailor made road trip holidays!
Fly into Chicago and
out of Los Angeles
2750 miles
approx
Includes flights, car & accommodation
Our 21 Night Route 66 Ultimate Trip holiday starts in Chicago and ends in Los Angeles: Chicago (3 nights), Springfield IL (1 night), St Louis (1 night), Springfield, MO ( 1 night), Tulsa (1 night), Oklahoma City (1 night), Amarillo (1 night), Tucumcari (1 night), Santa Fe (1 night), Gallup (1 night), Winslow for Petrified Forest & Painted Desert (1 night), The Grand Canyon (1 night), Monument Valley (1 night), Williams (1 night), Las Vegas (2 nights) including helicopter tour over the famous strip, Santa Monica / Los Angeles (2 nights)
Arrive in the Windy City, pick up your hire car and spend the next 3 nights in Chicago. Our recommendations include the Willis Tower, the second tallest building in the USA and the “magnificent mile”.
Collect
Car
Chicago,
IL
4 Star
Hotel
Today you’ll begin your “Mother Road” adventure. Retrace old 66 through Chicago, through rural Illinois into Springfield where Abraham Lincoln lived prior to his presidency. You can visit his home and burial places.
200
miles
Springfield,
IL
3 Star
Hotel
There's just 100 miles to drive to St Louis, known as the Gateway to the West. You’ll be able to drive a short section of the original brick road in Auburn, Illinois before walking the “Chain of Rocks” bridge, opened in 1929 to take traffic over the Mississippi River.
100
miles
St Louis,
MO
3 Star
Hotel
You’re heading through the Ozark Mountains today towards Springfield in Missouri where, in 1926 a road linking Chicago and Los Angeles was agreed. Originally planned as Route 60, but was finally designated as Route 66. Springfield is known as the birthplace of Route 66.
215
miles
Springfield,
MO
Historic
Hotel
Today, you’ll visit three States! Just after Joplin you’ll leave Missouri and head into Kansas. Don’t blink though - there’s just 13 miles of Route 66 in Kansas - but they’re a good 13 miles! Next up is Oklahoma, and don’t miss the famous Blue Whale of Catoosa!
180
miles
Tulsa,
OK
3 Star
Hotel
Just a short drive today at a mere 115 miles. You’re continuing your journey through Oklahoma - don’t miss the famous “Sidewalk Highway” section of Route 66 between Miami and Afton. So called because it was a single lane, just 9 foot wide section of the original Route 66.
115
miles
Oklahoma City, OK
3 Star
Hotel
Route 66 cuts through the Texas panhandle - On the list of must-see places today is the Provine Service Station, Route 66 Museum in Clinton, U-Drop Inn and of course the Cadillac Ranch in Amarillo
260
miles
Amarillo,
TX
3 Star
Hotel
Adrian, Texas is the midway point of Route 66 - a great photo opportunity. You’ll pass the ghost town of Glenrio on the Texas and New Mexico border. Tucumcari feels like an old 1950s classic American town.
115
miles
Tucumcari,
NM
Historic
Motel
Santa Fe, the New Mexico state capital was on the original Route 66 from 1926 until realignment in 1937. The Santa Fe loop can be missed out if you prefer to follow the later alignment - in this case, you can drive directly from Tucumcari to Albuquerque.
115
miles
Santa Fe,
NM
Historic
Motel
Drive west through Albuquerque and various small towns with some great old cafes, motels and gas stations and pass the Continental Divide before arriving in Gallup where you’ll stay in a historic hotel frequented by stars of the silver screen.
200
miles
Gallup,
NM
Historic
Hotel
As you cross into Arizona you will want to spend a couple of hours at the Petrified Forest and Painted Desert before you arrive in Winslow where you can take a photo “Standin' on the Corner” made famous from the Eagles song Take It Easy.
130
miles
Winslow,
AZ
4 Star
Hotel
At Flagstaff you’ll leave Route 66 temporarily to head north to the Grand Canyon. Your hotel will be near the south rim and you’ll want to make sure you get to see sunset in this wonderful National Park.
140
miles
Grand Canyon,
AZ
3 Star
Hotel
It’s worth an early alarm call today to watch sunrise over the Grand Canyon. Then you’ll drive along the rim and up to Monument Valley where you’re in for another breathtaking sunset. You’ll stay in a private cabin in Monument Valley itself and this is the view from your bedroom window!
175
miles
Monument
Valley, UT
Private
Cabin
Today you’ll head back down to Route 66 and Williams, a wonderful old town known as the Gateway to the Grand Canyon. It has real wild west feel to it with some great shops, restaurants and bars. You can also see the Grand Canyon railway trains here.
215
miles
Williams,
AZ
Historic
Hotel
Whilst Las Vegas is not actually on Route 66, it is an enjoyable detour during your road trip. Enjoy the fun and entertainment this city has to offer.
If you prefer to miss Las Vegas and stick to original Route 66 let us know.
220
miles
Las Vegas,
NV
4 Star
Hotel
Your trip includes a flight in a luxury Airbus helicopter featuring leather theater-style seating. You’ll soar high above the world-famous neon landscapes including Bellagio, Allegiant Stadium, Caesars Palace, historic downtown and more! If you prefer not to take this helicopter tour, please let us know.
Helicopter
Tour
Las Vegas,
NV
You’ll leave the huge resorts and neons in your rear view mirror and begin your final run to Santa Monica Pier today. You will pass through some great Route 66 towns such as Barstow and Victorville before arriving in LA and the end of your epic Route 66 road trip.
270
miles
Los Angeles,
CA
3 Star
Hotel
Make the most of your final morning in Los Angeles today. Perhaps you’d like to see the famous Hollywood sign or walk down Rodeo Drive. This evening you’ll catch your overnight flight back to the UK.
Return
Car
Fly
Home
Take a helicopter flight over the Las Vegas Strip's bright lights, capture a new perspective of the Vegas Valley plus see Red Rock Canyon, or journey out to the natural wonder that is the Grand Canyon. We have a selection of different trips and durations available which can be incorporated into your trip or purchased separately.
Based in Kingman, Arizona, our Route 66 Destination Consultant can be available for guided or walking tours in the region for groups of all sizes. Renowned road trip author Jim Hinckley has an extensive knowledge of Route 66. Please let us know if you would like to meet Jim for an afternoon or evening on your road trip.
You’ll stay in Santa Fe on our standard itinerary, but we definately recommend an extra day here.
All per person prices (pp) shown on this website are based on two adults sharing. Where hotel ratings are shown, these are US ratings, half stars are rounded up to the next full star. RouteTrip USA and RouteTrip are registered trademarks of RouteTrip USA Ltd. *T&Cs Apply. **On most full packages subject to availability. ***Free mobile data is included for most packages during your USA or Canada holiday and subject to usage limits.