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Home > Planning & Reservations > Trip Ideas > Family Road Trips > Route 66

Route 66 Road Trip

Discover Our Heritage in the Nation’s Heartland

Before a web of interstate highways cris-crossed the country, Route 66 was known as the Main Street of America. It earned this title due to the millions of migrants who traveled its many miles, seeking a better life out West. And it was along this route that modern America sprang up—motels, fast-food restaurants, and one-of-a-kind roadside attractions. Retrace the path of so many before, and take a nostalgic journey through pure Americana.

Total Length: 2,248 miles

States Included: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, California

To plan your road trip, use our search along the route tool to find hotels on Route 66—just enter your starting and ending points to get started.

Want suggestions for things to do and see on the way? Here are some of the most popular points of interest:

Chicago - IL

Whether you begin or end in the Windy City, spending several days in Chicago is a must. Autumn is lovely season to visit, as the glittering waters of Lake Michigan warm the air. The city offers some of the best art, science, and cultural museums in the world, sure to engage the entire family. It also boasts fascinating architectural landmarks and plenty of delicious (and inexpensive) local cuisine.

St. Louis - MO

World-famous for its soaring Arch, St. Louis and its surrounding region have plenty to offer. The city itself is filled with distinctive neighborhoods, as well as ample parks and museums. Cahokia Mounds State Park, the largest pre-Columbian city north of Mexico, is just minutes away across the river in Illinois, and Mark Twain’s birthplace of Hannibal is only a short drive north.

Cadillac Ranch and Amarillo - TX

A public art installation created in 1974, Cadillac Ranch is a collection of Cadillacs that have been plunged nose-first into the ground below. Visitors are encouraged to participate in the ongoing evolution of the sculpture by adding their own graffiti to the exteriors of the cars. The striking desert landmark has appeared in many films and music videos over the years, and is possibly the most iconic roadside attraction in the country.

Grand Canyon and Flagstaff - AZ

Arizona is fortunate enough to have two famous holes in the ground. The Grand Canyon is of course the most famous, but Meteor Crater is nearly as breathtaking. Formed 50,000 years ago by a space rock the size of a house, the crater is almost a mile across and over 500 feet deep. Though you can’t climb into it, a tour along the rim will give your family some truly spectacular views.

Los Angeles and Santa Monica - CA

In the original days of Route 66, families migrating west ended their journey in the promised land of California—and today, Santa Monica Pier marks the official end of Route 66. The city of Santa Monica is a charming neighborhood of mom and pop shops, and is walking distance from Venice Beach and Marina del Rey. Los Angeles, of course, has endless attractions—and your car is the best way to discover it all!

Complete your road trip with a rental car from Avis, Budget or Hertz. You will enjoy discounts of up to 35% and double, triple or quadruple bonus points towards your next Reward Night stay.

Book online or call:
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(1 888 465 4329)

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Route 66 Road Trip

Discover Our Heritage in the Nation’s Heartland

Chicago - IL

St. Louis - MO

Cadillac Ranch and Amarillo - TX

Grand Canyon and Flagstaff - AZ

Los Angeles and Santa Monica - CA

Book online or call:

1 888 HOLIDAY

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