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Original Route 66

Chicago, Springfield il, St. Louis, Springfield mo, Tulsa, Oklahoma City, Amarillo, Santa Fe, Winslow, Meteor Crater NM, Barstow, Los Angeles & more

This version of the old Route 66 road trip is one for the purists! It stays true to original or the old Route 66 route for the entire drive. This old school road trip along the “MotherRoad” will not disappoint.


Original Route 66 14 nights

All of our American road trips can be tailored to meet your requirements. Do you have more or less than 14 days for your road trip? No problem, we can bolt on extra nights to allow more time to explore or shorten the number of destinations as required. Just let us know when requesting your quote.

It was amazing! Every day was a REAL adventure. 


Chicago shoreline

Day 1

Arrive in Chicago

After touching down at Chicago O'Hare, you'll jump in a cab and head downtown towards one of the world's greatest skylines. After settling into the hotel that we have carefully selected for you, you'll have three nights and two full days to really get to grips with this wonderful city which sits on the shore of beautiful Lake Michigan. Should you want longer to explore Chicago, then just let us know when you call for a quote.

  • Key location: Chicago, IL
  • Chicago, IL

Chicago River

Day 2

Explore Chicagoland

Most visitors to Chicago head straight to 'Magnificent Mile', a vibrant, bustling area which is home to upscale shops, trendy restaurants and posh hotels. Landmarks include the historic Chicago Water Tower, the neo-Gothic Tribune Tower and the 100-story Hancock Center, which has a rooftop observation deck called 360 Chicago. Spend the rest of the day exploring some of the other attractions found north of the Chicago River. These include Navy Pier, Wrigley Field and the beaches found along the shoreline of Lake Michigan.

  • Key location: Chicago, IL
  • Chicago, IL

Millennium Park

Day 3

Explore the Windy City

On your final full day in Chicago, we recommend that you spend time visiting the cities attractions that are located south of the Chicago River. Some of America's very best museums are found here, these include the Art Institute, the Alder Planetarium and the Field Museum of Natural History. Be sure to stroll around Millennium Park too, you'll find world famous outdoor artworks like Cloud Gate and Crown Fountain for those all important Social Media snaps. Lastly, before leaving town, make sure you spend at least one evening partying at Buddy Guy’s Legends Nightclub.

  • Key location: Chicago, IL
  • Chicago, IL

Pontiac, IL

Day 4

Set off down Route 66

Start your engines, historic Route 66 awaits. After collecting your holiday wheels from a downtown location, we recommend you head to Jackson Blvd where you can pass the small Route 66 sign that marks the beginning of your road trip adventure. Driving Route 66 through Illinois is super easy, as it's really well signposted and surprisingly rural once you've left the city of Chicago. Along the way to Springfield, you'll enjoy highlights such as Route 66 obsessed Pontiac and the historic Standard Oil Gas Station in Odell. Once you arrive in historic Springfield, history enthusiasts will want to visit Abraham Lincoln’s Tomb, the Lincoln Presidential Museum and the Lincoln Home.

  • Key location: Pontiac, IL
  • Springfield, IL
  • 202 Miles

Famous St Louis Arch

Day 5

Cruise over to St Louis

Onto St. Louis today which sits on the banks of Mississippi River. Highlights include the Missouri Botanical Gardens, Citygarden and the iconic Gateway Arch National Park. If you have time be sure to try and catch a baseball game here at the Cardinal's stadium which is right in the heart of the city. Remember, that you'll be provided with a detailed Road Trip Pack which will guide you through all the Route 66 roadside attractions and much more.

  • Key location: St Louis, MO
  • St Louis, MO
  • 97 Miles

Meramec Caverns

Day 6

Iconic Route 66 stop - Meramec Caverns

Today, you'll continue south through the State of Missouri. En route, we recommend you stop by Meramec Caverns which are located in the Ozarks region, the caverns are an extensive set of limestone caves offering memorable underground tours. You’ll finish the day in Springfield, Missouri which is officially recognised as the birthplace of Route 66.

  • Key location: Meramec Caverns
  • Springfield, MO
  • 216 Miles

Philbrook Museum

Day 7

Tulsa Today

Continue west along the Mother Road, you'll pass through Joplin before skimming through a corner of the state of Kansas and into Oklahoma. Once you're in the city of Tulsa, we highly recommend a visit to the Philbrook Museum, home to a vast art collection, all housed in an Italian style villa surrounded by large idyllic gardens.

  • Key location: Tulsa, OK
  • Tulsa, OK
  • 181 Miles

Oklahoma City Memorial

Day 8

Onto Oklahoma City

En route, we recommend that you fill up with gas and delicious soda at Pops which is an iconic stop located on Route 66 in the town of Acadia. Once you've arrived in Oklahoma City, we recommend a visit to the Bricktown District of the city for a bite to eat at one numerous diners and restaurants found here. Lastly, before leaving town, consider visiting the moving Oklahoma City National Memorial which remembers the victims and survivors of the 1995 Oklahoma City bombing. Again, remember your Road Trip Pack will inform you of all the alternative attractions that are located here.

  • Key location: Oklahoma City, OK
  • Oklahoma City, OK
  • 106 Miles

Amarillo...this way!

Day 9

Travel to Texas today!

Your Road Trip Pack will show you the way to Amarillo, it's found due west in the heart of the Texas Panhandle. You'll pass some awesome Route 66 museums along the way, which are packed with nostalgic Americana, classic cars and more. Once you hit Amarillo, there's only one place for any true road-tripper to go for dinner. The Big Texan Steak Ranch & Brewery is simply a must, just make sure you arrive hungry as the portions are HUGE.

  • Key location: Amarillo, TX
  • Amarillo, TX
  • 260 Miles

Cadillac Ranch

Day 10

Your 6th state in 7 days!

Hello New Mexico! On the way from Amarillo to Santa Fe, you’ll have the chance to visit some classic Route 66 holiday attractions. These include Cadillac Ranch, Midpoint Cafe and the Route 66 Auto Museum in Santa Rosa. You’ll finish the day off in Santa Fe, New Mexico which lies along the path of the original Route 66 route, today it's home to adobe style buildings, beautiful resorts and swanky spas.

  • Key location: Cadillac Ranch
  • Santa Fe, NM
  • 290 Miles

The Painted Desert

Day 11

Witness geological wonders

Included in your Road Trip Pack you'll find plenty of detailed suggestions about what to do and see en route. One of our favourites is the Meteor Crater near Winslow in Arizona. El Morro is a detour worth considering too, you'll see 'Inscription Rock', a large sandstone pueblo where travellers since the 17th century have left messages. Another highlight of the day is The Painted Desert, which offers up multicoloured rock formations to amaze. After a busy day, you'll arrive in the classic Route 66 stopover town of Flagstaff for a one night stay.

  • Key location: Meteor Crater
  • Flagstaff, AZ
  • 384 Miles

Hackberry General Store

Day 12

Desert roads and classic Route 66 towns

The iconic small towns of Route 66 keep on coming today, you'll pass through Seligman, Hackberry, Oatman and Amboy on your way west to Barstow. Be sure to have your camera ready, so that you can capture classic Mother Road snaps as you go. Today is the last lengthy drive of the holiday, the mileage is nothing to be overly concerned about. You'll soon eat up the miles as you cruise along the open roads of Arizona and California, listening to your road trip soundtrack as you go.

  • Key location: Barstow, CA
  • Barstow, CA
  • 368 Miles

Route 66 - Done !

Day 13

Mojave Desert and LA glamour

Last stop - Santa Monica! The Santa Monica Pier signals the final stop of your Route 66 holiday. To celebrate the conclusion of your 2,200 mile journey, we suggest you enjoy a rewarding meal at one of the Pier's many eateries that overlook the Pacific Ocean.

  • Key location: Santa Monica
  • Los Angeles, CA
  • 130 Miles

California Dreamin'

Day 14

Chill or explore, the choice is yours

Spend the day relaxing after your road trip or head out to explore Los Angeles. There's plenty to keep you busy, Hollywood is synonymous with glitz and glamour and is the most visited part of the city. Just a short drive northeast of here lies the Griffith Observatory, perched high on a hill overlooking the urban sprawl. This famous landmark is well worth a visit and it also offers great views of the legendary Hollywood sign too. Tomorrow, you'll have the morning to continue exploring LA before flying home overnight to the UK. Lastly, please remember that should you wish to add some pool or beach days at the end of the holiday then just let know when you call for a quote.

  • Key location: Los Angeles, CA
  • Los Angeles, CA

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