15-Nights Historic Route 66 Road Trip: Chicago to Santa Monica - Road Trips from $3,061

Itinerary Details

Day 1: Chicago

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Arrive at Chicago's O'Hare International Airport and transfer independently to your hotel. Depending on your time of arrival you might have time to see a little bit of the city. Chicago has the nickname "The Windy City" but if you know the story behind its moniker, it has little to do with wind. The city is rightly renowned for its dramatic architecture and the 'Chicago Loop' is the famous and vibrant area where you see great architecture with delightful eateries, chic shops, and boutiques to boot. Apart from boasting some of the tallest buildings in the world, Chicago is proud of many excellent museums, delightful Lincoln and Millennium Park, and its world-famous deep-dish pizza. Overnight Chicago.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Step outside today and experience mile after magnificent mile of a truly great cosmopolitan city. Stand on the corner of Michigan and Adams, marked as the starting point of Historic Route 66. Enjoy coffee and a big breakfast at Lou Mitchell's, a Chicago institution since 1923 and a must for Route 66 travelers. Stroll the lakefront, peruse the shops, bike the parks, grab a Chicago Dog, or explore the city's incredible sights and architectural treasures including Willis Tower, one of the tallest buildings in North America. Overnight Chicago.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Get ready, because today starts an unforgettable journey into the then and now of America along Historic Route 66. This legendary old road passes through a variety of pure Americana landscapes and takes in some of the country's biggest, oldest, and most peculiar sites along the way. Begin your journey by following the traditional east-to-west path of Route 66 from Chicago to St. Louis, Missouri, cruising through endless cornfields and flat prairies. En route, don't miss Wilmington's most photographed 'citizen', the larger-than-life green Gemini Giant, and Atlanta's Bunyan Giant, a 19-foot statue of Paul Bunyan holding a giant hot dog. In Springfield, stop at the Cozy Dog Drive-In, the birthplace of the corn dog, and explore the legacy of Abraham Lincoln with a visit to the Lincoln Home National Historic Site. Once in St. Louis, the largest city along Route 66, you can follow in the footsteps of legendary explorers Lewis & Clark by visiting the historic sites found throughout the city, including the Gateway Arch, the nation's tallest monument. Overnight St. Louis.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Continue through the Ozark Highlands of southern Missouri to Springfield, recognized as the birthplace of Route 66. En route, stop at Meramec Caverns, an extensive set of natural limestone caves whose formations and colors are as unique as they are beautiful. Adding to the pleasure of exploring the caves is learning that Jesse James used them as a hideout and took advantage of the underground river to escape through the 'back door.' Overnight Springfield.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Cut through the southeastern corner of Kansas on your way to Oklahoma City this morning. The Oklahoma section of Route 66 contains more drivable miles than any other state, as well as several miles of the original 9-foot road segment that served Oklahoman families, headed west in search of better opportunities during the 1930s. Make sure to stop to view the beloved 20-foot tall cement Blue Whale in Catoosa, a landmark along Route 66, and the Cyrus Avery Route 66 Memorial Bridge in Tulsa honoring the "Father of Route 66's" memory and connection to the historic highway. Once in Oklahoma City, the state's capital, be sure to check out the old Route 66 motels, gas stations, and numerous vintage buildings. Overnight Oklahoma City.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Continue to Amarillo, located in the pancake-flat plains of the Texas Panhandle. This area of Texas was once the buffalo-rich grasslands of the Great Plains, inhabited by bands of Kiowa and Comanche Indians. Stop at the Route 66 Museum in Clinton and experience six decades of Route 66 history. See Shamrock's Tower Station and the U-Drop Inn Cafe whose towering spire is still a reminder of the booming business it once saw. See the first restored Phillips 66 gas station in McLean and in Groom, the leaning water tower, and a 150-foot-tall stainless-steel cross. Once in Amarillo, you might want to stop at Big Texas Steak Ranch where you can attempt their 72oz. steak challenge. Overnight Amarillo.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Before leaving Amarillo, you need to visit Cadillac Ranch for a memorable photo opportunity. It was invented and built by a group of art hippies from San Francisco and their silent partner, Amarillo billionaire Stanley Marsh 3. He wanted a piece of public art that would baffle the locals, and the hippies came up with a tribute to the evolution of the Cadillac tail fin. In 1974, ten Caddies were driven into one of Stanley Marsh 3's fields, then half-buried, nose-down, in the dirt. They are still an iconic view today. This is the land of tumbleweeds, cattle, cotton, and oil. Later in the day, you cross another state border into New Mexico, driving through what once was the hunting ground of the Comanche Indians. Overnight Albuquerque.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Enjoy a relaxing day in Albuquerque, New Mexico's largest city sitting in the high desert. Founded in 1706 as a Spanish colony its modern downtown core is in stark contrast to Old Town Albuquerque with its artist's community and historic adobe buildings such as the San Felipe de Neri Church, five museums, and many shops and boutiques. Every October, the city hosts the International Balloon Fiesta, the world's largest gathering of hot-air balloons at the Balloon Fiesta Park, with its 47-acre launch field. Overnight Albuquerque.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

To get a true sense of the Old Route 66, detour today to New Mexico's state capital, Santa Fe. Founded on the ruins of an abandoned Indian village and steeped in history, Santa Fe is the oldest capital in the U.S., and although it lost its place on Route 66 in 1938, it remains one of the most picturesque cities in the state. At one time this was the end of the old Santa Fe Trail, the earliest trade route linking the American frontier back east with the far west. Plan to visit one of Santa Fe's famous art galleries, art markets, or museums full of traditional and contemporary art, including works by their own Georgia O'Keeffe, or shop for authentic creations you just won't find anywhere else.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

This morning, the state of Arizona welcomes Route 66 travelers with an overwhelming display of trading posts. View huge concrete tepees that stand at the foot of brilliant red-rock mesas en route to Petrified Forest National Park, the only park in the National Park System containing a section of Historic Route 66. Here you will come face-to-face with over 13,000 years of human history and one of the world's largest and most colorful assemblies of petrified wood, historic structures, and archeological sites. Catch a sunset over the Painted Desert from the park's Kachina Point before heading to Holbrook. Once in Holbrook, stop at the Wigwam Motel whose steel and concrete teepees featuring modern conveniences have welcomed guests since the 1950s. Overnight Holbrook.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Continue to Meteor City, a true vintage trading post whose distinctive dome can be seen for miles along this stretch of Route 66. Traveling towards Grand Canyon National Park, you pass through Flagstaff until you reach the quaint mountain town of Williams where you can experience the personality of an authentic Western village. The Grand Canyon is a world-famous natural wonder that defies description until you see it with your own eyes. Spend as much time as possible discovering the distinct South Rim of the canyon. Stop at one of the dramatic lookouts, walk part of the Rim Trail or along the historic Hermit Road, visit a Photo Hot Spot, or climb to the top of a stone Watchtower for panoramic views that extend over one hundred miles on a cloudless day. Overnight Williams.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Today, you are heading west to Seligman, a small town located along Historic Route 66. Evidence of the old road is all along Seligman's main street where motels, cafes, and Route 66 gift shops beg to be explored. From here you'll join Route 66 and travel along the longest remaining stretch of this historic route which runs through the downtown of one of Arizona's hidden treasures, Kingman. At the Arizona-Nevada border, Hoover Dam makes for an awe-inspiring stop. Considered the largest single public works project in the history of the U.S. and an Arizona landmark, Hoover Dam is full of history and offers a mesmerizing view of the Colorado River and Lake Mead. Continue to Las Vegas, a desert oasis of neon lights and a city that, surely, needs no introduction. Overnight Las Vegas.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Enjoy a full-day Las Vegas style. Walk the famous Strip lined with mega-resorts and flashing neon lights, place a bet at one of the many casinos, dine at world-class restaurants, catch the latest must-see show, shop designer boutiques, ride a rollercoaster, lie by the pool... the list goes on. With so much to do, 24 hours in a day hardly seems like enough.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

When leaving this morning, take the last opportunity to photograph the iconic Welcome to Las Vegas sign. Spectacular scenery surrounds you as you travel through the Mojave Desert. Make sure to visit Calico Ghost Town, an authentic Old West silver mining town, which offers visitors the opportunity to share in its rich history and enjoy the natural beauty of the surrounding desert environment. Rejoin Route 66 in Barstow where a collection of historic photographs and artifacts related to Route 66 and the Mojave Desert communities are on display at the Route 66 Mother Road Museum. Continue through Pasadena, Los Angeles, West Hollywood, and Beverly Hills to Santa Monica for a true Hollywood ending to your cross-country journey. Park and venture the last few blocks on foot to view the "End of the Trail" sign on Santa Monica's Pier. This sign officially marks the western end of Historic Route 66.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Spend the day strolling along the beaches of Santa Monica or browse the adjacent indoor and outdoor shops at Third Street Promenade. Alternatively, explore L.A.'s one-of-a-kind destinations, playgrounds of the rich and famous, and architectural gems. Universal Studios Hollywood and Anaheim's original Disneyland Park are also located within easy driving distance.

Rental Car: Hertz - Chicago Ohare Apto Los Angeles Airport

Make your way to Los Angeles International Airport for your flight home unless you plan to extend your stay in California.