Holiday Overview
Travel one of the world's most famous roads and get your kicks on Route 66, spanning 2400 miles, eight states and three time zones. Nostalgia lovers treasure Route 66's long, colourful history and small town ambiance. Getting there isn't half the fun, it's all the fun!
Duration: 16 days / 15 nights
Start: Chicago
Finish: Los Angeles
US States you will visit: Illinois, Missouri, Oklahoma, Texas, New Mexico, Arizona, Nevada, California.
Highlights of this holiday are:
- The big city buzz of Chicago
- The Cadillac Ranch
- Historic Santa Fe
- The Grand Canyon
- Las Vegas
- Los Angeles
Route 66 Fly Drive Holiday includes:
- Return flights from the UK
- Car Hire - Intermediate Car
- Intermediate Car with Gold Cover - Unlimited mileage, Full tank of fuel, 3 additional drivers, Collision Damage Waiver (CDW), $1 million liability coverage, Zero excess in the USA
- 2 nights accommodation in Chicago
- 1 night accommodation in St Louis
- 1 night accommodation in Springfield
- 1 night accommodation in Oklahoma
- 1 night accommodation in Amarillo
- 3 nights Accommodation in Albuquerque
- 1 night accommodation in Holbrook
- 1 night accommodation in Williams
- 2 nights accommodation in Las Vegas
- 2 nights accommodation in Los Angeles
Day 1 - Arrive in Chicago
Arrive in Chicago and independently transfer to hotel
Day 2 - Chicago - Explore the Windy City
Day at leisure to explore Chicago, perhaps grab breakfast at Lou Mitchells, a route 66 Icon, or stroll along the lakefront. In the evening visit one of Chicago's Blues Bars.
Day 3 - Chicago - St Louis 297 miles
Pick up your chosen car and embark on Route 66
Day 4 - St Louis - Springfield 216 miles
Continue through the Ozark Highlands to Springfield, En Route stop at Meramec Caverns, an extensive set of Limestone caves once used as a hiding place by the outlaw Jessie James.
Day 5 - Springfield - Oklahoma 286 miles
Travel onwards to Oklahoma, via Tulsa and the Cyrus Avery Route 66 Memorial Bridge. Once in Oklahoma check out the old Route 66 motels gas stations and vintage buildings.
Day 6 - Oklahoma - Amarillo 260 miles
Continue to Amarillo, located in the flat plains of Texas, stop at the Route 66 museum in Clinton and the resorted Phillips 66 gas stations in McLean and Groom
Day 7 - Amarillo - Albuquerque 289 miles
Head onwards past the famous Cadillac Ranch onto the Midpoint Café, in Adrian perhaps sampling one of their famous "ugly crust" pies.
Day 8 - Albuquerque
Spend the day exploring Albuquerque, a treasure trove of Route 66 landmarks. The Old Town offers a taste of New Mexico's Spanish colonial past and the Indian Pueblo Cultural Centre traces the history of the regions Native Americans.
Staying at Fairfield Inn Marriott
Day 9 - Albuquerque
Take a side trip to the charming and picturesque city of Santa Fe, Santa Fe is the nations oldest State Capital and full of history, take in one of the cities art galleries and enjoy a meal in one of Santa Fe's many restaurants.
Staying at Fairfield Inn Marriott
Day 10 - Albuquerque - Holbrook 233 miles
Head onwards to Arizona, stop off at the Petrified Forest National Park, the only National Park on Route 66, enjoy a sunset over the Painted Desert from Kachina Point before arriving in Holbrook.
Day 11 - Holbrook - Wiiliams 123 miles
Continue onwards to Meteor City, pass through Flagstaff and Williams onto the awe inspiring Grand Canyon, spend the day at the South Rim, walk part of the Rim Trail and visit a photo hot spot, before returning to Williams for the night.
Day 12 - Williams - Las Vegas 220 miles
Next stop the bright lights of Las Vegas, drive through Seligman and Kingman where old Route 66 cafes and motels still flourish. Visit the Hoover Dam beforearriving in Las Vegas
Day 13 - Las Vegas
Enjoy a full day of leisure in Las Vegas, walk along the famous strip, dine in world class restaurants, take in the latest show and perhaps try your luck in one of the many casinos that are synonymous with Las Vegas
Staying at Luxor
Day 14 - Las Vegas - Los Angeles 270 miles
Drive through the Mojave Desert and stop at Calico, an old silver mine Ghost Town continue through Pasadena, Hollywood and Beverley Hills, before arriving at the "end of the trail" sign at Santa Monica Pier
Day 15 - Los Angeles
A full day of leisure in L.A. Visit Hollywood and the walk of fame perhaps do some Star spotting in Beverly Hills, or visit one of L.A.s famous theme parks
Staying at Hilton Anaheim
Day 16 - Depart from Los Angeles
Return your rental car at Los Angeles Airport prior to departure
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Image Gallery
Route 66 Road
Cadillac Ranch
Grand Canyon
Las Vegas
Route 66 Road Sign
Santa Fe
Chicago
St Louis Arch
Route 66 Mural - view on our route 66 fly drive holiday
Oklahoma City
Flagstaff
Williams
Grand Canyon
Las Vegas
Hollywood
Los Angeles Beach
USA Holiday Stopovers
Why not add in the 'Land of Fire and Ice' - Iceland -on your way to your holiday in the USA. We have put together a great stopover in Iceland for 2 or 3 nights which includes accommodation and the Golden Circle Trip which includes visits to the Gullfoss Waterfall, the geo thermal area of Geysir and Thingvellir National Park.
If you are travelling to the west coast of America, why not add a couple of nights stay in New York which includes accommodation and tickets for the 'Top of the Rock' observation platform for an iconic view of the city skyline. This can be done either on your way out or on the way back.
Alternative Holidays That May Interest You
Below you will find a small selection of 2026, 2027 holidays that may interest you. Remember, we tailor-make each holiday to your exact needs, so please call us on 0800 917 5742 and let one of our Holiday experts design the perfect trip for you
Canyon Adventure Fly Drive Holiday
- Las Vegas
- Bryce Canyon
- Moab
- Mesa Verde
- Grand Canyon
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Buzzing Las Vegas
- Stunning National Parks
7 Nights from £2260pp
Pacific Coast Highway Road Trip
- Los Angeles
- Pismo Beach
- Monterey / Carmel
- Yosemite National Park
- San Francisco
- Receive a free case of wine
- Save £300 per booking book by 31 October
- The exciting buzz of Los Angeles & Hollywood
- California's beautiful coastline
- The stunning natural beauty of Yosemite
- San Francisco with its delightful sightseeing
7 Nights from £2300pp
Best of New England Fly Drive
- Boston
- Portland Maine
- Bar Harbor
- White Mountains
- Killington
- The Berkshires
- Mystic
- Yarmouth MA
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Visit beautiful maritime towns
- See the beautiful mountains of New Hampshire & Vermont
- Experience historic Boston
14 Nights from £2985pp
California Fly Drive
- San Francisco
- Sonoma
- Lake Tahoe
- Yosemite National Park
- Death Valley
- Los Angeles
- San Diego
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Wonderful San Francisco
- Awesome Yosemite
- The heat of Death Valley
- Cool Pacific Breezes
11 Nights from £3100pp
Talkin' Texan Self Drive Holiday
- Dallas
- Austin
- Fredericksburg
- Bandera
- San Antonio
- Corpus Christi
- Houston
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Iconic Texan Cities
- Working Cattle Ranch
- The Alamo
12 Nights from £3145pp
The Wild West Fly Drive Holiday
- Denver
- Cheyenne
- Rapid City
- Cody
- Jackson
- Salt Lake City
- Moab
- Durango
- Colorado Springs
- Receive a free case of wine
- Save £300 per booking book by 31 October
- Wild West Cowboy Country
- Iconic scenery & Wildlife
- National Parks
15 Nights from £3175pp