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The Ultimate Road Trip Itinerary on Route 66 From Chicago to Los Angeles

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The construction of the major interstate should have been the end of Route 66, but the historic roadway still attracts travelers from around the world who want to experience the unique small towns and quirky roadside attractions that have made the route so famous. Covering more than 2,400 miles, the journey will take visitors the long way round from Chicago to Santa Monica. If it is nostalgia and a window into classic Americana that you are after, Route 66 is the perfect choice.

Day One - Explore Chicago

View from the Chicago River

Route 66 famously begins in the Windy City. Before you set out on the long drive through the heartland of America toward Los Angeles, you should spend some time exploring Chicago itself. Located on the shore of Lake Michigan, Chicago is the largest city in the mid-west, and features many exciting attractions.

No visit to Chicago would be complete without taking a walk through Millennium Park. Be sure to snap an Instagram-worthy photo at the unique Cloud Gate Sculpture. If you've got the time, take a walk down Navy Pier and ride the Centennial Wheel for a great view of the city.

Day Two - Visit the museums of Route 66

Abraham Lincoln House in Springfield

Leave the interstate and start following Historic Route 66 through some of the small towns of Illinois. You'll come across some interesting roadside attractions like Ambler's Texaco Gas Station en route to Pontiac. When you arrive in Pontiac, you'll be able to see a huge collection of Route 66 memorabilia and visit the local auto museums.

Continue south toward Springfield along Route 66. Break up your trip with a stop in the small town of Atlanta, where you will be able to visit the local Arcade Museum. That's not the only quirky attraction you'll see either. In nearby Lincoln, get a photo of the world's largest covered wagon. Before you end your day in Springfield, visit the sites dedicated to Abraham Lincoln in the city where he once lived and worked.

Day Three - Cross the famous Rainbow Bridge

Rainbow Bridge Route 66

There are plenty more unique attractions in store on day three along the way to Tulsa, Oklahoma. Pull in at carthage and see the famous 6 Drive In, which still shows films today. Pass through Galena and cross the historic Rainbow Bridge in Baxter Springs as you continue into Kansas.

If you're looking for a lunch spot, you'll find it in Vinita. It may have lost the title, but the local McDonald's was once the largest in the world. Stop in for a meal before continuing on to Chelsea, where you'll find Ed Galloway's Totem Pole Park. Your final destination for the day is just a short drive away.

Day Four - Visit the unique Cadillac Ranch in Texas

Cadillac Ranch Amarillo

Get ready for a long drive across Oklahoma and into Texas. If you need a refreshment along the way, stop in at Pops in Arcadia for a drink. You shouldn't really miss the store, as there is a 66ft tall soda bottle out the front. As you pass by Oklahoma City, make sure you pull in to Elk City and visit the National Route 66 and Transportation Museum.

There will be plenty of sights to explore in Amarillo. The city features some unique attractions - the strangest being the Cadillac Ranch. The site is made of cars decorated with grafitti and partially buried in a field. If you'd like to take in some of the natural scenery, head south of Amarillo to Palo Duro Canyon.

Day Five - Drive through New Mexico

Albuquerque Old Town

Leave Texas and head west into New Mexico. Along Route 66, you'll discover plenty of fascinating towns and Native American sacred sites in the state. Your first stop of the day should be Tucumcari, a town with its own Route 66 Museum and a large collection of fossils in the Mesalands Dinosaur Museum.

See more classic cars at the Route 66 Auto Museum in Santa Rosa, and visit the vibrant Blue Hole, a popular diving location in the middle of the desert! When you arrive in Albuquerque, spend some time exploring the city's Old Town. See the remnants of the old Spanish settlement and learn about the Native American connection to the area.

Day Six - Experience the Wild West

Petrified Forest National Park, Arizona

Before you leave New Mexico for Arizona, visit the Sky City Cultural Center and Haak'u Museum for a guided tour and a window into the Native American culture. Upon crossing the Arizona border, you'll soon arrive at the stunning Petrified Forest National Park. This is the only national park on Route 66, and it is well-worth a visit.

Spend the night in Holbrook, where your choice of accommodation includes a teepee-shaped motel room. You'll find many classic American sights in the town including saloons and old trading posts. This is the perfect spot to learn more about the Wild West.

Day Seven - Cross from Arizona to California

Winslow Arizona

Spend the day exploring some of the unique wonders of Arizona. If you are a fan of the Eagles, you may want to pay a visit to the Standing on the Corner Park, which commemorates the famous line from "Take it Easy". Any photographers should also stop by the Twin Arrows Trading Post Ruins.

You can break up your drive with a stop in Flagstaff, where you'll find plenty of cafes and restaurants. If you're traveling with family, the Route 66 Zipline in nearby Williams is a fun activity. Don't miss the small town of Oatman, where the surroundings will make you think you've stepped back in time to an old western mining town. Stop for the night just across the Californian border in Needles.

Day Eight - Head to Santa Monica

Santa Monica sunset street

Travel through rural California and enjoy the remote, desert scenery. Stop in at Elmer's Bottle Tree Ranch, a unique attraction that has become a staple of Route 66. The unique artwork features hundreds of trees made of glass bottles. Another exciting stop along California's stretch of Route 66 is San Bernardino, where you can visit the site of the original McDonalds.

To reach the end of Route 66, you'll need to cross Los Angeles. Spend a bit of time exploring the city, and see famous sights like Hollywood Boulevard, Universal Studios and Beverly Hills. Santa Monica Pier marks the official end of Route 66, providing you with fantastic views of the Pacific Ocean.

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