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 Route 66: Classic Trail

14 night Route 66 holiday including the Grand Canyon and Las Vegas

Drive Route 66 from Chicago to Los Angeles via Las Vegas in just 2 weeks with a side trip to The Grand Canyon.

This self drive holiday takes you along Route 66 at a reasonably fast pace. You’ll spend a couple of nights in Chicago giving you enough time to see the main sites before embarking on your approx 2450 mile journey to Santa Monica in California. This holiday itinerary includes side trips to 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, 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.

If you have an extra night or more, we can modify the trip to slow the pace down a little if desired.

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

2450 miles

Includes flights, car & accommodation

route 66 holiday

Our 14 Night Route 66 Classic Trail holiday starts in Chicago and ends in Los Angeles: Chicago (2 nights), Springfield IL (1 night), St Louis (1 night), Springfield, MO ( 1 night), Oklahoma City (1 night), Amarillo (1 night), Santa Fe (1 night), Holbrook for Petrified Forest & Painted Desert (1 night), The Grand Canyon (1 night), Las Vegas (2 nights) and Santa Monica / Los Angeles (2 nights)

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Call our Route 66 Travel Experts on:

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Your Itinerary

route 66 chicago holiday

Days 1 & 2:
Chicago (2 nights)

Arrive in the Windy City, pick up your hire car and spend your first two nights in Chicago. Our recommendations include the Willis Tower, the second tallest building in the USA and the “magnificent mile”.



4 Star

route 66 road trip

Day 3:
Springfield, Illinois

Today you’ll begin your “Mother Road” adventure. Retrace old 66 through Illinois to the State Capital, Springfield. This city is famously associated with Abraham Lincoln who lived here and is buried in Oak Ridge Cemetery



3 Star

route 66 package

Day 4:
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.


St Louis,

3 Star

route 66 holiday usa

Day 5:
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




route 66 holiday package

Day 6:

There's three US states to drive through today! Leaving Missouri, there is just 13 miles of Route 66 in Kansas before arriving in Oklahoma. You’ll also drive the famous 9 foot wide “sidewalk highway” section of 66


Oklahoma City, OK

3 Star

route 66 cadillac ranch

Day 7:
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




route 66 blue swallow

Day 8:
Santa Fe

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 before Tucumcari which has a real 1950s feel to it. Your overnight stop is in Santa Fe, the New Mexico capital.


Santa Fe,


route 66 petrified forest

Day 9:
Petrified Forest

Continuing West through New Mexico you’ll pass many vintage motels, especially in Grants and Gallup. Be sure to have your camera handy. As you cross into Arizona you will want to spend an hour or so at the Petrified Forest and Painted Desert before arriving at Holbrook




route 66 grand canyon

Day 10:
The Grand Canyon

Highlights today include the Jack Rabbit Trading Post and Standin’ on the Corner in Winslow, famously mentioned in the Eagles song “Take It Easy”. Get an early night, you’ll want to catch sunrise at the Grand Canyon. Conveniently your hotel is only minutes from the South Rim.


Grand Canyon, AZ

3 Star

route 66 las vegas holiday

Days 11 & 12:
Las Vegas (2 nights)

Get an early start to catch sunrise at the Grand Canyon before spending a few hours enjoying the breathtaking views. Then you'll drive to Las Vegas via Hoover Dam for two nights. If you don’t fancy Las Vegas, we can easily alter your trip itinerary.


Las Vegas,

4 Star

route 66 california holiday

Days 13 & 14:
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.


Los Angeles,

3 Star

route 66 hollywood

Days 15 & 16:
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.



 Get road trip ready with our road trip pack and app!

A few weeks before you depart on your epic Route 66 trip, you can expect to receive an exclusive pack in the post containing the amazing EZ66 Guide, information on downloading your personalised itinerary on our app and a few other goodies!

Easily scroll through your itinerary and use the buttons at the bottom of each day to view your accommodation, any tour vouchers, latest weather forecast and flight info. See our recommended attractions, museums and places to eat on the live map and use the messaging feature if you need to contact us during your trip.

Click on the image to have a sneak peak of our app.
grand canyon helicopter tour
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.

local tour guide
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.

pacific coast route 66
Pacific Coast Highway

Take a drive up Highway 1, known as the Pacific Coast Highway. If you fancy driving as far as San Francisco, take a look at our Route 66+1 road trip

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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. **On most full packages subject to availability. ***On request, subject to availability and refundable deposit required.