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Route 66 Classic Fly Drive

Chicago * Springfield * St Louis * Springfield * Oklahoma City * Amarillo * Santa Fe * Gallup * Flagstaff * Las Vegas * Los Angeles

Take the Classic American Fly Drive o­n the Route 66, 16 days from Chicago to the Pacific Coastal town of Santa Monica. Get your kicks on Route 66!

17 days from £2,733 per person twin share + flights


Day 1-2 - UK - Chicago 

Your Route 66 holiday begins with a United Airlines flight from London Heathrow to Chicago. Collect your car from the airport and check in to your hotel. Chicago is home of America's tallest building, one of the world's largest office buildings and most significantly the starting point of Route 66! From shopping to museums and pop-culture this vibrant city boasts something for everyone. Check out "The Ledge Experience" at the Skydeck where you can step out onto a fully enclosed glass ledge from the 103rd floor of the Willis Tower. 

Overnights (2): Chicago

Day 3 - Chicago - Springfield, Illinois (220 miles)

Start your day with breakfast at Lou Mitchells in the heart of Chicago's Loop, a local fixture since 1923. In Wilmington see the 23ft high Gemini Giant who has gazed down o­n visitors since 1965. Experience an authentic American Diner at the Polka-a-Dot Drive-In famous for their chili-cheese fries! It’s worth stopping in Pontiac, a town Time magazine called o­ne of the best small towns in America! Take a walking tour to see the 19 outdoor murals and visit the Route 66 Hall of Fame and Museum. Snap a photo of your car parked in front of the giant Route 66 mural! Overnight in Springfield, capital of Illinois where Abraham Lincoln lived until he left to become the 16th president.

Overnight (1): Springfield 

Day 4 - Springfield - St Louis (100 miles)

Traveling through the heartland of America today you'll have the opportunity to drive a piece of Route 66 dating back to the 1930's where you can imagine yourself in an Illinois long gone. In St. Louis make time to visit the Gateway Arch or take a paddleboat cruise along the Mighty Mississippi river front. A visit to St. Louis isn't complete without a visit to Ted Drewes Frozen Custard with its legendary "concrete" malts so thick you can hold them upside down and they won't fall out of the cup!

Overnight (1): St Louis

Day 5 - St Louis to Springfield, Missouri (218 miles) 

St. Louis and Springfield are two old Route 66 towns. Almost every exit drops you within a few minutes’ drive to mom & pop motels, trading posts and gas stations offering wonderful photo opportunities. Missouri also holds o­ne of the greatest Route 66 attractions - Meramec Caverns which have existed for the past 400 million years.

Overnight (1): Springfield, MO

Day 6 - Springfield - Oklahoma City (285 miles)

There are many historical sites worth a visit today including the courthouse in Carthage a magnificent Romanesque Revival building constructed with Carthage stone with medieval castle features that include turrets, towers, and arches. We travel to Oklahoma today, a mecca for old-road fans with more still-drivable miles of Route 66 than any other state.

Overnight (1): Oklahoma City 

Day 7 - Oklahoma City - Amarillo (259 miles) 

Today offers an opportunity to visit the Route 66 museum in Clinton where you'll experience the history and culture of each decade of Route 66. As you enter Texas you'll be back o­n Route 66 for some famous stops along the Mother Road including McLean, o­ne of the few real-time capsules where you will be transported back in time for a true Route 66 experience. Tonight, visit the famous Big Texan Steak Ranch home of the free 72 oz steak (provided you can consume the steak and fixings within an hour!). It's a true "Texas" experience and Route 66 legend.

Overnight (1): Amarillo 

Day 8 - Amarillo - Santa Fe (292 miles)

Just outside Amarillo you can visit Cadillac Ranch a row of 10 perfectly aligned old Cadillac cars buried nose-first into the barren landscape. Writing graffiti on or otherwise spray painting o­n the old cars is highly encouraged! As you continue east pass through Adrian, Texas the Route 66 midpoint of the 2,278 miles between Chicago and Santa Monica. Arrive into Santa Fe where you will have 2 nights to enjoy the arts and culture of this beautiful city.

Overnights (2): Santa Fe 

Day 9 - Santa Fe 

You will likely want to start your day exploring at The Plaza in the centre of town. The Plaza is the pulsating heart of the city where fiestas and fairs are held annually. Be sure to include a visit to the Palace of the Governors; built in 1610 it remains the oldest continuously used public building in the United States. Santa Fe ranks as the country's third largest art market and boasts some of the finest galleries, shops and museums in the southwest.

Day 10 - Santa Fe to Gallup (200 miles)

A short drive today takes you to Albuquerque a city famous for its annual hot air Balloon Fiesta. Just outside Albuquerque visit the famous Sandia Peak Aerial Tramway and be transported 10,378 feet high to an observation desk affording an 11,000 square-mile panoramic view of the Rio Grande Valley and the Land of Enchantment. If you're looking for a route off the beaten path today, you can travel old Route 66 from Albuquerque to Gallup. This is one of the most scenic portions of Route 66 with huge mesas, jumbled boulders, distant mountain peaks and a deep red tone to the earth.

Overnight (1): Gallup

Day 11 - Gallup - Flagstaff (185 miles) 

Don't miss a drive through the Petrified Forest National Park where you can see 250-million-year old logs that have literally been transformed into rocks in shades of red, purple, amber and blue. Arrive in Flagstaff this afternoon where you'll spend two nights and enjoy many options for shopping, dining and entertainment.

Overnights (2): Flagstaff

Day 12 - Grand Canyon Sightseeing  

Today's highlight is a visit to Grand Canyon National Park, o­ne of the Seven Natural Wonders of the World. Time your day to arrive in Williams before 9am and you'll catch the Wild West shootout and entertainment before the departure of the Grand Canyon Excursion Train. Next to the train depot is a small Route 66 Museum and Shop. We recommend reserving a scenic helicopter flight to coincide with your arrival at the Grand Canyon. Exit via the East Rim highway and stop at the Cameron Trading Post for a Navajo Taco or browse for souvenirs before returning to Flagstaff in the evening.

Day 13 - Flagstaff - Las Vegas (279 miles)

The longest stretch of old road starts from Seligman and you can follow it to Kingman before turning north to the glittering lights of Las Vegas. About 30 miles outside Las Vegas you'll cross the Colorado River o­n the Hoover Dam which forms the border between Arizona and Nevada. Considered to be the world's largest dam it was a true engineering marvel at the time of its construction in the 1930s.

Overnights (2): Las Vegas

Day 14 - Las Vegas

A full day to explore the "city that never sleeps". Explore the iconic casinos, cool down o­n a river rafting trip down the Colorado River or take an exciting helicopter tour to the Grand Canyon west rim and the amazing glass Skywalk. In the evening, be sure to take in one of the world-class shows!

Day 15 - Las Vegas - Los Angeles (284 miles)

Re-join the old road in Barstow for the last leg of your Route 66 journey to Santa Monica. Santa Monica's Third Street Promenade and the Venice Beach boardwalk are close by your hotel. Near where Santa Monica Boulevard dead-ends at Ocean Boulevard, a brass plaque marks the official end of Route 66, the "Main Street of America" After taking a stroll along the Santa Monica Pier continue to your hotel.

Overnights (2): Los Angeles

Day 16 - Los Angeles  

A full day to explore the sprawling city of Los Angeles, the City of Angels. A short drive takes you to many famous sights like Universal Studios, Hollywood, Mann's Chinese theatre, Beverly Hills or Disneyland. Or perhaps a relaxing day o­n the beach would be the perfect way to recharge your batteries at the end of this fabulous holiday!

Day 17 - Los Angeles – UK

A final morning to relax and enjoy California before check-out time when your tour ends. Return your rental car to the airport and check in for your flight home. 

Day 18 - Arrive UK


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Standard HotelsUpgraded Hotels
ChicagoChicago Essex Inn Hotel Lincoln Chicago
Springfield, ILHoliday Inn Enfield SpringfieldCrowne Plaza Springfield
St LouisBest Western St Louis Inn Crowne Plaza St Louis Downtown
Springfield, MOBest Western Route 66 Rail Haven Best Western Plus Coach House
Oklahoma City Best Western Plus Saddleback InnBest Western Plus Saddleback Inn
Amarillo, TXBig Texan Motel Holiday Inn Amarillo West
Santa FeCourtyard by Marriott Santa Fe Inn of the Governors
GallupComfort Suites Gallup Best Western Plus Gallup Inn & Suites
FlagstaffBest Western Pony Soldier Inn & SuitesDoubletree by Hilton Flagstaff
Las VegasGolden NuggetThe Venetian
Los AngelesBest Western Plus Gateway Santa Monica Le Meridian Delfina Santa Monica

Tour Price Includes:

  • Scheduled flights with United Airlines from Heathrow
  • Airport taxes, security charges and the Air Passenger Duty
  • 16 nights accommodation, room only
  • 16 days fully inclusive hire of an intermediate car with unlimited mileage, LDW, Extended Protection, Sales Tax, State Tax and Airport Fees
  • Itinerary, maps and detailed driving instructions

Not Included:

  • Weekend flight supplements £30 each way Friday-Sunday
  • Extra charge applies to renters under 25 years of age
  • One way drop off fee for rental car, payable locally
  • Hotel Parking charges if applicable
  • Entrance fees to National Parks, attractions, activities and excursions
  • Fuel for hire car
  • Meals

Our Price Guarantee

All offers are subject to availability. Once a booking is confirmed your holiday price is 100% GUARANTEED against any increase in price such as currency exchange fluctuations or fuel surcharges. Other companies may surcharge you by up to 10% more!

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Holiday Information


Chicago Essex Inn


Hotel Lincoln Chicago



Holiday Inn Enfield Springfield


Crowne Plaza Springfield



Best Western St Louis Inn


Crowne Plaza St Louis Downtown



Best Western Route 66 Rail Haven


Best Western Plus Coach House



Best Western Plus Saddleback Inn


Best Western Plus Saddleback Inn



Big Texan Motel


Holiday Inn Amarillo West



Courtyard by Marriott Santa Fe


Inn of the Governors



Comfort Suites Gallup


Best Western Plus Gallup Inn & Suites



Best Western Pony Soldier Inn & Suites


Doubletree by Hilton Flagstaff



Golden Nugget


The Venetian



Best Western Plus Gateway Santa Monica


Le Meridian Delfina Santa Monica