Route 66 – Two Week Trip - 15 Days

Starting in: Chicago, Illinois

Ending in: Santa Monica, California

Total driving distance approximately 2,434 miles: with suggest side-trips approximately 2,650 miles


Route 66 is many things to many people. Each person tends to experience the road differently. There is a spirit, a feeling that resides along this highway. The spirit of Route 66 lives in the people and their stories, the views and structures, and travelers’ perceptions of them along the route. To gain a true understanding of Route 66 and the spirit of Route 66, there is no substitute for driving the highway. In the years following World War II, Route 66 made the transition from being simply a road connecting Chicago and Los Angeles to a place in and of itself, as much the focus of travel as the final destination. The close of the war marked the end of gasoline rationing and the scarcity of rubber tires, making car travel affordable again. Magazines such as Life, Time and the Saturday Evening Post did feature articles on national highways, locating good places to eat, spend the night, and visit along the way. The highways of America, no longer solely a means of going from one place to the next, became a new space for excitement, interaction, and experience. No one song captured the widespread desire to be a part of this new, emerging highway culture more than Bobby Troup’s “Route 66.” Traveling west along 66 in 1946, Bobby Troup had already written the first two stanzas of “Get Your kicks on Route 66” upon his road map before he reached Los Angeles. Nat King Cole later recorded the song, and it quickly found a central place in America’s musical history. The catchy lyrics were the perfect accompaniment on the car radio as thousands of Americans took to the new highways in search of new homes, visiting friends, or just to cruise about. We invite you to follow the dreams of many Historic Route 66 travelers before you and become a part of an American legend!

Trip Highlights

  • Chicago
  • Route 66
  • Grand Canyon
  • Santa Monica


Day 1

Arrival: Chicago, Illinois

Welcome to the Windy City! The beginning of Route 66, which originates in Chicago, has moved a few times. Currently Adams Street at Michigan Avenue is the starting point! Upon arrival, discover Chicago’s famous sights and sounds. Once the home of gangster Al Capone, the Windy City still provides endless excitement. By day Chicago’s high rising architecture and North America’s tallest building, the Sear’s Tower, provide a perfect backdrop for this cosmopolitan city. At night, the city is transformed by jazz clubs, lounges, fine dining, and excellent theaters. You may wish to extend your stay to explore more that Chicago has to offer – from shopping on the “Magnificent Mile” to renowned museums including the Art Institute, Museum of Science and Industry, and the Field Museum of Natural History.

Overnight: Hilton Garden Inn Chicago Downtown South Loop in Chicago, Illinois

Day 2
CHICAGO TO ST. LOUIS, MISSOURI (approx. 4.5 hours/299 miles)

Head south through Chicago to the town of McLean, famous for its Dixie Truck Stop which opened only a couple of years after the Route 66 had been inaugurated in 1926, and which has only been closed for only one day since. Continue through the coal mining area of Illinois along the Pontiac Trail. Here and there you can visit” the old road”; just pieces of pavement that still exist along the newer version. Don’t miss the “Our Lady of the Highway Statue” or Litchfield and the Paris Stop Cafe. Visit Meramec Caverns the oldest tourist attraction on the Mother Road. The site has been welcoming Route 66 wanderers since 1933 for a fascinating underground look at the region’s history and geology.

Missouri legends say frontier outlaw Jesse James hid men, loot, and horses in the massive cave. Before Jesse’s arrival, French colonial miners and Civil War soldiers used the cavern’s natural minerals to manufacture gunpowder. During the attraction’s early days, owners took American roadside art to new heights by turning painted barn roofs into billboards promoting the Meramec Caverns across the country. North of downtown St. Louis, the Old Chain of Rocks Bridge was Route 66’s original crossing over the Mississippi River. Follow the Riverfront Trail a hiking and biking path – from the Old Chain of Rocks Bridge to the Gateway Arch, St. Louis ultimate monument to the great American West. Wagon train pioneers paved the way for Route 66 by establishing dusty frontier trails to the west from St. Louis in the 1800s. Today the Arch sits at the head of I-44, pointing modern travelers to the west.

Stop in the Arch’s fascinating Museum of Westward Expansion to marvel at the rugged covered wagons and say a silent “thanks” for the invention of shock absorbers and pavement. On any given day you might find wedding parties, British television crews, Japanese tour groups, classic car clubs, German journalists, and Americans from all 50 states waiting in line at Route 66’s most famous refreshment stop – Ted Drewes Frozen Custard.

Overnight: Hampton Inn St. Louis Downtown at the Gateway Arch in St. Louis, Missouri (Complimentary Continental Breakfast)

Day 3
ST. LOUIS - SPRINGFIELD, MISSOURI (approx. 3.5 hours/214 miles)

Leaving St. Louis, Route 66 continues south and west through the beautiful Ozark Mountains alongside I-44 all the way to Springfield in southwest Missouri. On the way, brown and white Route 66 road signs point toward stops that range from historic to kitschy and everywhere in between. Walnut bowl factories, wineries, cow pastures and knock-’em-dead scenery dot the mythic American roadside. Amidst the gentle mountains, lush forests, deep blue lakes, and swift streams of the Ozarks sits Missouri’s third largest city.

Overnight: Best Western Route 66 Rail Haven, Springfield, Missouri (Complimentary Continental Breakfast)

Day 4
SPRINGFIELD - TULSA, OKLAHOMA (approx. 3 hours/189 miles)

Travel through the famous towns of Lebanon and Conway and the old beautiful courthouse in Carthage on the way into the last main town of Missouri, Joplin. Be sure to stay on the old Route 66, as it will enter the Sunflower State of Kansas for fourteen miles. Here, in the town of Baxter Springs, a restaurant now occupies a bank, which was once robbed by none other than Jesse James. The safe is still there, although it now serves as a restroom. And then, the Sunflower state of Kansas for fourteen miles before heading down to check out Miami, Oklahoma with its beautiful Art Deco Coleman Theatre where Will Rogers performed regularly. This evening stroll the sidewalks of Cherry Street, the historic shopping district in the heart of Tulsa.

Overnight: Holiday Inn Tulsa City Center, Tulsa, Oklahoma

Day 5
TULSA - OKLAHOMA CITY (approx. 1.5 hours/110 miles)

Along the way discover the mom-and-pop roadside diners, old-fashioned service stations, and motor courts. Arcadia is best known for its famous Round Barn, built in 1898 and recently restored to its former glory. On the ground floor is the gift shop with a Route 66 satellite exhibit. Chandler features authentic ghost signs on the sides of buildings, a huge WPA era native stone Armory, an old brick Phillips 66 cottage-style gas station and many buildings downtown are on the National Historic Register. Stroud is the home of the Rock Café, a famous Route 66 landmark, first opened in 1939. Built in giraffe stone, the building has the ghost sign of a vintage Coca-Cola advertisement that is well placed for picture taking. The Oklahoma City Stockyards is the largest stocker/feeder cattle market in the world. Attend live auctions on Monday and Tuesday mornings. Take a stroll through Cowtown, which offers a variety of shops from old time general stores and tack shops to western duds and jewelry. Travel to the National Cowboy and Western Heritage Museum that portrays the rugged individualism and romantic spirit of the frontier. It features a superlative collection of classic and contemporary Western Art plus thousands of artifacts and objects. Explore a life-size western town, interactive exhibits, The American Cowboy Gallery, The American Rodeo Gallery, The Native American Gallery, and the Western Entertainers Gallery.

Overnight: Best Western PLUS Saddleback Inn, Oklahoma City, Oklahoma (Complimentary Full-Service Hot Breakfast)

Day 6
OKLAHOMA CITY - AMARILLO, TEXAS (approx. 4 hours/269 miles)

Head west through El Reno, crossing the mile-long bridge near Bridgeport. In Clinton, the heart and soul of Route 66 country, visit the Route 66 Museum. The journey takes us into the ” Texas Panhandle” continuing through the oil town of Shamrock to Amarillo, the place where you can “Step into the Real Texas®”. From canyons to cowboys, big steaks to big spaces, everything Texas is famous for is right here. Amarillo is the largest Texas city on Route 66. Now, a stretch of the old highway, along Sixth Ave. between Georgia and Western Streets, has been revived into a stretch of antique shops, restaurants, and cafes.

Overnight: The Big Texan Motel, Amarillo, Texas

Day 7
AMARILLO - TUCUMCARI, NEW MEXICO (approx. 2 hours/170 miles)

After passing through Cadillac Ranch, which is home to one of the quirkiest attractions along the old route, the Cadillac Ranch, where ten Cadillac, by now covered in colorful graffiti, left by the thousands that visit this bizarre monument, stick out of the dirt of a roadside field, head south to the magnificent Panhandle Plains Museum with its outstanding Indian collections and visit the stunningly beautiful Palo Duro Canyon, once a hideout for the Comanche. How about the ghost town of Glen Rio where you can stand with one foot in New Mexico and the other in Texas? New Mexico presented an exotic and nearly foreign travel experience to early motorists on Route 66. Not only did the landscape transform dramatically as the miles flew by, from the flat expanses of the eastern llano to the climactic red bluffs of Gallup, but place names and historical scars on the land also spoke with Castilian, Pueblo or Navajo accents. Continue to Tucumcari. Don’t miss the neon sign of the Blue Swallow Motel, a classic Route 66 highlight. In true motor-hotel tradition, this motel used to have garages next to the rooms.

Overnight: Blue Swallows Motel, Tucumcari, New Mexico

Day 8
TUCUMCARI - ALBUQUERQUE (approx. 2.5 hours/170 miles)

In 1926, Route 66 entered eastern New Mexico, following the tracks of the Southern Pacific Railroad. West of Santa Rosa, it left the tracks, turned north, and became even more of a historical roadway by joining with the Santa Fe Trail and El Camino Real. Leaving Santa Rosa, the road followed the Pecos River Valley – a route used by Native American tribes for years to reach the Pueblo lands of the Rio Grande. Just south of Las Vegas, New Mexico, it picked up the Santa Fe Trail and followed it to the capital city. Like very few places, present day Santa Fe is a living link to its past. Tracing the city’s history is as easy as walking the picturesque streets of this 400-year-old village. The area’s Native American culture goes back thousands of years and is alive in the city’s art and traditions just as the Hispanic heritage lives in Santa Fe’s customs. At Santa Fe, the Original Road would retrace El Camino Real south over La Bajada, through several of the Pueblo communities on the Rio Grande and into Albuquerque. It entered New Mexico’s largest city from the north and crossed the Rio Grande on the Barrelas Bridge. The city began to develop a north-south growth pattern along 4th Street as auto repair shops, gas stations, motels and restaurants began to spring up next to the Mother Road. Visit Historic Old Town, where the Villa of Albuquerque was founded in 1706, Stop at the Indian Pueblo Cultural Center, and discover arts and crafts from New Mexico’s 19 pueblos; Indian dances are held on weekends year-round. At nearby Petroglyph National Monument over thousands of years, hunting parties chipped an estimated 17,000 petroglyphs into a dramatic lava rock escarpment.

Overnight: Best Western PLUS Rio Grande, Albuquerque, New Mexico

Day 9
ALBUQUERQUE – GALLUP (approx. 2 hours /170 miles)

West of Albuquerque, travelers curved along Route 66 through red mesa lands and stone cliffs straight out of western movie scenery. Through Laguna and Ácoma Pueblo lands, the winding, two-lane highway worked its way on past Budville Trading Company. Built in 1928 and run by Bud Rice and his wife, it was one of the top auto service companies in the Southwest.

Here motorists could get water bags, a quick tune-up, and a thorough tire check. Then on to the Villa de Cubero, built by a family of Indian traders in 1937, a modern auto court available for overnight or extended stays. Here, far from water, novelist Ernest Hemingway wrote most of The Old Man and the Sea, and Lucille Ball stayed during her divorce from Desi Arnaz. A highpoint of today is Ácoma Sky City. the oldest continuously inhabited settlement in the United States. Sky City rests on a rock mesa top 357 feet above the surrounding valley floor.

Inaccessible except by steep footpath until modern times, Ácoma is one of history’s more ingenious fortified cities. The crown jewel of Ácoma is San Esteban Del Rey Mission, with one of the most beautiful and architecturally creative Catholic mission interiors to be found in North America. Travel on “Route 66” through the railroad and uranium mining town of Grants, down Santa Fe Avenue with its Southwestern Art Deco atmosphere. Today’s final destination is Gallup, the city’s many trading posts, galleries and shops project an utterly unique blend of Native-American culture, with genuine Indian and Southwest Hispanic arts & crafts in rich abundance. The greatest concentration of interesting turn-of-the-century architecture is located along Route 66.

Overnight: Historic El Rancho Hotel, Gallup, New Mexico

Day 10
GALLUP - FLAGSTAFF, ARIZONA (approx. 3 hours/209 miles)

There’s no forest quite like the Petrified Forest anywhere else on earth. Giant petrified logs litter this 93,533-acre landscape, uniquely preserved (“petrified”) through the happy circumstance of time, climate, chemistry, and place. Also included in the park’s 93,533 acres are the multi-hued badlands of the Chinle Formation known as the Painted Desert. Late afternoon will find you in Holbrook, where the 1898 courthouse, now on the National Register of Historic Places, is the centerpiece of town.
Imagine a giant meteor, weighing several hundred thousand tons, zipping toward Earth at nearly 40,000 miles per hour! Visit Meteor Crater and view the results of its impact, a gaping chasm 550 feet deep and more than 4,000 feet in diameter. Exhibits, movies, and lectures vividly show and tell about the awesome event. See where the astronauts trained, by taking a guided rim tour. Flagstaff’s Route 66 has “Mom and Pop” restaurants, cafes, and roadhouses, motor courts, and unusual attractions. Among them is the Museum Club, Flagstaff’s official Route 66 roadhouse. For fifty years, this legendary Flagstaff landmark has hosted such country music legends as Willie Nelson and Waylon Jennings.

Overnight: Best Western PLUS Pony Soldier (Complimentary Continental Breakfast), Flagstaff, Arizona (2 nights)

Day 11
FLAGSTAFF - GRAND CANYON - FLAGSTAFF (approx. 3.5 hours/199 miles)

Depart Flagstaff on Highway 89 north past Sunset Crater Volcano and descend onto the vast Marble Plateau of the Navajo reservation. Stop at the trading posts and enjoy an interesting blend of history and authentic Native American art-and-craft items. At the intersection of Highway 89 and 64, travel west on 64 to Grand Canyon National Park. Your first stop within the canyon will be the Desert View Overlook, where visitors can climb the stately Watch Tower to enjoy the sweeping views of the magnificent Grand Canyon. The canyon offers many lookout points. While in Grand Canyon Village, stop to enjoy the historic Bright Angel and El Tovar lodges and the Hopi House, a National Historic Building. Return to Flagstaff via scenic Highway 180 and experience the beauty of the ponderosa-pine and aspen forests.

Day 12
FLAGSTAFF – KINGMAN (2.5 hours/170 miles)

Take I-40 west of Flagstaff, and you’ll arrive at Williams, which has maintained many of its original Route 66 businesses; continue on I-40 to Ash Fork and exit at Crookton Road, the longest stretch (150 miles/240km) of the original Route 66. Continue along old Route 66 to Seligman, home of the Sno-Cap Drive-in, a genuine 1950s fast-food stop and ice-cream parlor, and on down the road to Grand Canyon Caverns, one of the largest dry caverns in the United States. The scenic drive winds through a succession of small communities named Hackberry, Valentine, Truxton, and Peach Springs, where time seems to have stopped in the ’50s and ’60s.

From Valle Vista, the newest community on old Route 66, you ‘ll take a seven-mile turn, the longest continuous curve on any U.S. highway. The next stop is Kingman, “Heart of Historic Route 66.” While in Kingman visit the Powerhouse Route 66 Museum.

Overnight: Best Western PLUS Kingman (Complimentary Continental Breakfast)

Day 13
KINGMAN - BARSTOW, CALIFORNIA (approx. 3.5 hours/259 miles)

Be prepared for steep grades and sharp curves (favored by switchback loving motorcycle riders) for the remainder of the journey along the longest stretch of Route 66 still in existence between Chicago and Los Angeles. It will take you to Oatman. Oatman, a genuine western ghost town, is famous as the honeymoon hideaway for Clark Gable and Carol Lombard.

Finally, head west and turn south toward Topock-Golden Shores and spend some time in Needles on the Colorado River. The town has several historic buildings, including ‘El Garces’, the Harvey House built in 1906, the Women’s Clubhouse and the Old Trails Inn, a 1930s vintage cabin court, once widely known as the Palms Motel. Afterwards you will be coming to the end of Route 66 and rejoining I-40. A few miles down the Interstate the Hwy 95 exit brings you back to Route 66. This portion of the old road was the pre 1931 alignment of Route 66 and led to the little desert community of Goffs, California. To many Route 66 enthusiasts the Mojave Desert stretch of the road represents nothing more than a desolate wasteland. This is in part because the traveler making his way along the old route today is confronted by long empty stretches of nothing. But what today’s traveler sees as emptiness is often the site of a once booming community. While most of the towns along National Trails Highway are small and while much of what has been is no longer, there is still a tremendous amount history to be found.

Barstow, named after William Barstow Strong, was the president of the Santa Fe Railroad at that time. The beautiful Railroad Depot was built in 1910 and also served as a Harvey House. Today it has been restored by the city of Barstow and is the site of the Route 66 Mother Road Museum.

Barstow is another Route 66 town that takes pride in its heritage. There is still much of Old Route 66 to see in Barstow. The famous El Rancho Motel, built with railroad ties from the defunct Tonopah & Tidewater Railroad, and El Rancho Cafe are Mother Road landmarks. And who could forget the Route 66 Motel on Main Street (Route 66).

Overnight: Quality Inn on Historic Route 66, Barstow, California (Complimentary Continental Breakfast)

Day 14
BARSTOW - SANTA MONICA (approx. 2.5 hours/140 miles)

As you drive Route 66 out of Barstow you will come to Lenwood, another Route 66 town on the National Old Trails Highway. The old highway leaves Barstow and Interstate 40 to follow the Mojave River through the old Route 66 towns of Lenwood, Hodge, Helendale, and Oro Grande to rejoin the Interstate at Victorville. Along the way ghostly shadows of the Mother Road can still be seen, such as the ruins of an old store between Hodge and Helendale. After Oro Grande, Route 66 crosses the Mojave River at a great old steel-truss bridge, a vintage Route 66 structure built in 1930. Once across the bridge you are entering Victorville, another town that got its start from the demand for cement at the turn of the century. During the hey-day of Route 66 Victorville had the western flavor that Hollywood was looking for and many an old B western was filmed in the area. The Summit Inn on Cajon Pass is a Route 66 landmark.

It has been serving travelers since 1952, providing a welcome break before or after navigating the treacherous pass. Cajon Pass, the famous gateway to San Bernardino and Southern California has long been an important natural route. Desert Indians had come this way for centuries followed later by Mountain Men and early Spanish and Anglo explorers. In the early 1800’s it was the southern end of the Old Spanish Trail, which led to Santa Fe, New Mexico. In 1861 a 12-mile toll road through the pass was built. The road linked San Bernardino and the coastal cities to the booming mining communities of the high desert. Cajon Pass was a natural route for the railroad when it came in 1885. In the late 1920’s the old trails over Cajon Pass became Route 66. Portions of the old road can still be seen by taking the Cleghorn Exit off I-15. Route 66 in this area has the distinction of being the first divided highway in the United States. There is still much to see of old Route 66 along Foothills Boulevard. Go slow and be on the lookout for the relics of the road tucked here and there between newer buildings. There are quite a few old motels and cafes along this stretch of Route 66 in San Bernardino, Rialto and Fontana. The Wigwam Motel is one of the most interesting ones. San Bernardino was founded in 1851 by Mormon pioneers.
Later this area became an important junction point for railroads and transportation to and from Los Angeles. The area also proved to be ideal for citrus growers. By the early 1900’s orange groves spread across the landscape from the mountains to the coastal plains making up what became known as the Inland Empire. These orange groves became a welcome sight for the traveler on Route 66. From Figueroa Street to Sunset Boulevard then on to Santa Monica Boulevard you will be following the last alignment of Route 66 to the Pacific Ocean. Santa Monica Boulevard travels through Hollywood, West Hollywood, Beverly Hills and finally Route 66 ends in Santa Monica at Palisades Park and the famous Santa Monica Pier on the Pacific Ocean.

Overnight: Hotel Carmel by the Sea, Santa Monica, California (Complimentary Continental Breakfast)

Day 15
Tour Ends

Head back home or add additional nights in Santa Monica.

Trip Includes

  • 14 hotel nights at published hotels (or similar), local hotel taxes and resort fees (except where mentioned), travel tips, maps, and brochures. Complimentary Breakfast subject to change at the hotel’s discretion.

Trip Excludes

  • Rental car, gas, parking fees, porterage, flights, airport transfers,
  • meals, unless otherwise specified in the tour description, park & attractions entrance fees, unless otherwise specified in the tour description, ferry charges, travel insurance.

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From $ 50
per Child 17 years and under with 2 paying adults

Trip Info