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 Route 66: Ultimate Trip

21 night self drive holiday on Route 66 and 10 States!

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!

Includes flights from UK, car hire and accommodation
Fly into Chicago and out of Los Angeles
You’ll drive approximately 2750 miles in total
 Includes Monument Valley, Grand Canyon & Las Vegas
Your trip can be tailored to suit your needs. Extra days can easily be added or we can shorten the trip if preferred
Your full road trip pack and itinerary will be sent to you
Your entire holiday package is ATOL protected


  • Tailor Made USA Holidays

    Let us create your dream bespoke holiday. Speak to us today.

route 66 itinerary holiday

Your Itinerary

route 66 chicago

Days 1 - 3:
Chicago (3 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

route 66 holiday package

Day 4:
Springfield, Illinois

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

route 66 uk

Day 5:
St Louis

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

route 66 usa

Day 6:
Springfield, Missouri

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

route 66 blue whale

Day 7:
Tulsa

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

route 66 oklahoma

Day 8:
Oklahoma

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 texas

Day 9:
Amarillo, Texas

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

route 66 trip

Day 10:
Tucumcari

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

route 66 road trip

Day 11:
Santa Fe

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

route 66 santa fe

Day 12:
Gallup

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

route 66 painted desert

Day 13:
Petrified Forest

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

route 66 grand canyon

Day 14:
Grand Canyon

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

monument valley route 66

Day 15:
Monument Valley

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

route 66 uk

Day 16:
Williams

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

las vegas holiday

Days 17 - 19:
Las Vegas (3 nights)

Whilst Las Vegas is not actually on Route 66, it is a great detour during your road trip. Enjoy the fun and entertainment this city has to offer.
If you prefer, you can miss Las Vegas and keep to Route 66 or you can visit Sin City and return to Route 66. Your choice!

220
miles

Las Vegas,
NV

4 Star
Hotel

la route 66 holiday

Day 20 & 21:
Santa Monica (2 nights)

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

hollywood route 66

Day 22 & 23:
LA & Fly Home

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

ez66 guide for travelers

Route 66 Guides

When you book your Route 66 holiday with us, you will receive the EZ66 Guide (left) in your road trip pack.

Click the button below for more information on three of our favourite Route 66 guides to help you along your way. There’s also a link to buy them if you wish!

MORE INFO
helicopter flight grand canyon

Helicopter Flight

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.

meet jim hinckley

A local guide in Arizona

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.

santa fe route 66

Extra night in Santa Fe

You’ll stay in Santa Fe on our standard itinerary, but we definately recommend an extra day here.

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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. **Subject to availability. ***On request, subject to availability and refundable deposit required. Client monies for flight inclusive bookings taken on or after 1st April 2021 are protected by a trust scheme provided by Protected Trust Services, any bookings before this date remain protected under our ATOL license  and insurances.