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Historic Route 66: From Chicago to Santa Monica

16 Days
Prices From:
US$ 2,572

FIRST-CLASS |SELF DRIVE: Still a bucket list item for many, Route 66 has an allure that suggests freedom, America’s wide-open spaces, supported by a rollcall of cities immortalized in the song (Get your Kicks) On Route 66. Chicago kicks it off in style before you, ideally, walk the last few blocks towards Santa Monica Pier where it ends. The Grand Canyon provides a moment of drama, but Route 66 purists will delight in all the old Route 66 motels, gas stations and vintage buildings that are featured along the entire trip. A road trip like no other

This 16-day Route 66 self-drive tour takes you from coast to coast, Chicago to Los Angeles, and features attractions both historic and quirky, as you might expect from America’s famous “Mother Road.” The route holds a special place in American hearts and history, evoking a simpler time when the automobile brought freedom to millions of travellers and tourists.
Your journey takes you from Chicago to Kansas, Texas to New Mexico and then Las Vegas, and onward to the California coast. Along the way, visit Amarillo’s Cadillac Ranch, stroll UNESCO-designated Santa Fe, experience Arizona’s Petrified Forest, visit two natural wonders – the Grand Canyon and the Hoover Dam – let loose in Las Vegas, and photograph the Route 66 “End of the Trail” sign in Santa Monica. Finish up by claiming your commemorative Route 66 certificate.

Arrive in Chicago on Day 1 and check in to your hotel. Wake early to explore the magnificent Windy City, beginning with the corner of Michigan and Adams, the official start of Route 66. Order some silver dollar pancakes at Lou Mitchell’s diner, a perennial route favourite since 1926. Stroll the lakefront, do some shopping, visit Navy Pier, or book a tour of the city’s justly-famous architectural treasures, including Willis Tower. End the night at a hopping live music venue.

It’s time to head off for St. Louis, Missouri, so pick up your rental car and head east, travelling through golden cornfields and prairies. Stop for a photo of the larger-than-life green Gemini Giant, or Atlanta’s Bunyan Giant. In Springfield, Illinois, try a Cozy Dog Drive-In corn dog and visit the Lincoln Home National Historic Site. Once in St. Louis, visit a historic site such as the 630-foot tall Gateway Arch.

Southern Missouri takes you through the rolling hills of the Ozark Highlands to Springfield, heralded as the birthplace of Route 66. En route, take a cue from bandit Jesse James and visit Meramec Caverns, one of the rarest and largest cave formations in the world: Jesse once hid out here.

The 380-mile Oklahoma section of Route 66 features such endearing attractions as a 20-foot tall cement Blue Whale in Catoosa and the Cyrus Avery Route 66 Memorial Bridge. In Oklahoma City, look for more Route 66 tributes in the form of classic motels, gas stations and vintage theatres. Head out later for some classic American BBQ or a juicy steak.
Crossing the prairie, rolling hills, and canyons of the Texas Panhandle, your next destination is the Oklahoma Route 66 Museum in Clinton. View the re-created diner, gleaming vintage cars, and replica vintage gas station. The 1930s Tower Station and U-Drop Inn Café are next, in all their pink Art Deco glory. Like your steaks on the big side? Consider the 72-ounce steak challenge at Big Texas Steak Ranch upon arrival in Amarillo.

Day 7 takes you from Amarillo to Albuquerque, New Mexico with a pit stop at the quirky Cadillac Ranch. Lovely Albuquerque sits on the River Grande and its Central Avenue is considered a treasure trove of Route 66 landmarks. Visit historic Old Town and the Indian Pueblo Cultural Center. Then spend your eighth day on a side trip to beautiful Santa Fe, famous for its Pueblo-style architecture, art galleries, markets, and the 17th-century Palace of the Governors museums. Santa Fe is a food lover’s dream: try a spicy New Mexican chile, buffalo tenderloin, or a silky tortilla soup for dinner.

Arizona welcomes you next. Be sure to visit the Petrified Forest National Park, assemblies of petrified wood, historic structures, and archaeological sites. Relish the peace and beauty of the grassland as you hike from scenic Tawa Point to the Painted Desert Visitor Center, or walk around the remains of a 100-room pueblo occupied by the ancestral Puebloan people over 600 years ago.

In historic Wild West Holbrook, Arizona – “the town too tough for women and churches” – stop at the postcard-worthy Wigwam Motel, with its steel and concrete 1950’s teepees. Yes, you can actually stay at this classic piece of American road trip culture. Pass by Meteor City, Flagstaff, and Williams en route to Grand Canyon National Park where you will spend the afternoon exploring the South Rim of the canyon, walking part of the Rim Trail or creating memories at a Photo Hot Spot.

The imposing Hoover Dam is next, before continuing on to Las Vegas for a bit of culture, Nevada style. Spend your thirteenth day sunning by the pool, throwing some dice, shopping, strolling The Strip, or experiencing the exhilarating immersive attraction, FlyOver. Visit a distillery or cocktail bar or dine at one of Vegas’ almost 3,000+ restaurants (800 of them, fine dining).

Head across the Mojave Desert for the California coast today, stopping at Calico Ghost Town, a historic silver mining town for a trip on the Calico Odessa Railroad, or a gold panning experience. Rejoin Route 66 in historic Barstow and visit the Route 66 Mother Road Museum. Continue through Pasadena, Los Angeles, West Hollywood, and Beverly Hills to Santa Monica to proudly view the “End of the Trail” Route 66 sign on Santa Monica’s Pier.

Enjoy a final day of minimal driving. Stroll the beaches of Santa Monica or shop at Third Street Promenade, or head into L.A. for a Universal Studios tour or try out the thrilling new Star Wars ride at Disneyland Park. The next day, return your rental car and head out for home, knowing you successfully drove historic Route 66.

At Goway we are experts at designing personalized itineraries to suit your special interests, tastes and budget. Let us arrange your ultimate travel experience today.
16 Days
Prices From:
US$ 2,572

Itinerary View Trip Map

Day 1


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

Duration2 nights
Day 2


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

Day 3

Chicago - St. Louis

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. Enroute, 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

Duration1 night
Day 4

St. Louis - Springfield

Continue through the Ozark Highlands of southern Missouri to Springfield, recognized as the birthplace of Route 66. Enroute, 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

Duration1 night
Day 5

Springfield - Tulsa - Oklahoma City

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 1930's. 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

Duration1 night
Day 6

Oklahoma City - Amarillo

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

Duration1 night
Day 7

Amarillo - Albuquerque

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

Duration3 nights
Day 8


Enjoy a relaxing day in Albuquerque, New Mexico’s largest city sat 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

Day 9

Albuquerque - Santa Fe - Albuquerque

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.

Overnight Albuquerque

Day 10

Albuquerque - Holbrook

This morning, the state of Arizona welcomes Route 66 travellers with an overwhelming display of trading posts. View huge concrete tepees that stand at the foot of brilliant red-rock mesas enroute 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 colourful 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 1950's.

Overnight Holbrook

Duration1 night
Day 11

Holbrook - Grand Canyon/Williams

Continue to Meteor City, a true vintage trading post whose distinctive dome can be seen for miles along this stretch of Route 66. Travelling 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 the 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

Duration1 night
Day 12

Grand Canyon/Williams - Las Vegas

Today, you are heading west to Seligman, a small town located along Historic Route 66. Evidence of the old road are 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


Duration2 nights
Day 13

Las Vegas

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

Overnight Las Vegas

Day 14

Las Vegas - Santa Monica - Los Angeles Area

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.

Overnight Los Angeles

Duration2 nights
Day 15

Los Angeles Area

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.

 Overnight Los Angeles

Day 16

Los Angeles

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

Other Information


Daily departures:  April 1 - October 31, 2023


  • 16 days Intermediate Car Rental with unlimited mileage (Mazda 3 or similar)
  • Detailed day by day itinerary
  • 2 nights first class accommodations in Chicago 
  • 1 night first class accommodations in St. Louis 
  • 1 night first class accommodations in Springfield
  • 1 night first class accommodations in Oklahoma City 
  • 1 night first class accommodations in Amarillo 
  • 3 nights first class accommodations in Albuquerque
  • 1 night first class accommodations in Holbrook
  • 1 night first class accommodations in Grand Canyon/Williams
  • 2 nights first class  accommodations in Las Vegas 
  • 2 nights first class accommodations in Los Angeles 


  • Car rental insurance
  • Travel insurance
  • International and domestic airfare & airfare taxes
  • Entrances fees to sites not explicitly listed as included
  • Meals and beverages not mentioned
  • Road tolls
  • Gratuities
  • Items of a personal nature
  • Visa fees if applicable


  • Gaze at Chicago’s Willis Tower, one of the tallest buildings in North America
  • Take a nostalgic ride along Historic Route 66
  • Get a bird’s eye view of the Gateway Arch in St. Louis
  • Lose yourself in the quiet beauty of Missouri’s Ozark Region
  • Experience the nation’s longest drivable stretch of Route 66 in Oklahoma
  • Pay an optional visit to Amarillo’s Cadillac Ranch, a ritual site on The Mother Road
  • Sample rich culture and the true Southwest in Albuquerque
  • Visit Santa Fe, a UNESCO designated City of Design, Crafts and Folk Art
  • Explore one of the best remnants of native Arizona grassland in Petrified Forest
  • View one of the 7 Natural Wonders of the World, the Grand Canyon
  • Pay an optional visit to Hoover Dam
  • Enjoy 24 Hour entertainment in glittering Las Vegas
  • Explore Calico Ghost Town
  • See the replica of the long-lost Route 66 “End of the Trail” sign at the Santa Monica Pier
  • Get closer to the stars at Grauman’s Chinese Theater, a Hollywood landmark


Prices are "from" per person based on twin/double share accommodation and for travel in low season. Seasonal surcharges and blackout dates may apply. Limited seat/spaces and all pricing is subject to change and availability. Rates for single or triple travellers are available on request. Additional terms and conditions apply for car rental - please inquire.

1 Oct 2023
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