Iconic Route 66, the worlds most famous road trip :
Trip Highlights

Day One

Resort: Chicago »
Hotel: Hotel Versey Days Inn by Wyndham Chicago »

Arrive at Chicago’s O’Hare International Airport (ORD) and proceed to your hotel after picking up your car rental at the airport, for a 2 night stay to explore Chicago, at your own pace. Chicago is a city with a rich history and a musical soul

Day Two

Resort: Chicago »
Hotel: Hotel Versey Days Inn by Wyndham Chicago »

Spend the day in Chicago at your leisure

Day Three

Resort: Springfield IL »
Hotel: Best Western Clearlake Plaza »

Today you will drive toward Springfield for an overnight stay. Along the way you will encounter the town of Bloomington home of the Historic Route 66 Memory Lane. Continue to Springfield for an overnight stay. Springfield became the Illinois state capital in 1837 with the help of a young lawyer and politician named Abraham Lincoln.

Day Four

Resort: St Louis »
Hotel: Red Roof Plus+ St Louis Forest Park »

Today, drive toward Missouri. Saint Louis is the largest city on Route 66 between Chicago and Los Angeles. It was founded on the banks of the Mississippi River in 1762 and became the ‘Gateway to the West’. Lewis and Clark left St. Louis on their famous journey across an unfamiliar land to the Pacific Ocean.

Day Five

Resort: Springfield MO »
Hotel: Sleep Inn Springfield - MO »

Depart St. Louis and continue on the trail of this historic road. Your next stop will be Rolla, home of the Totem Pole Trading Post, built in 1933. Note the curbs on the roadside, these were intended to make sure traffic stayed on the road, only to tip cars over in practice. Continue to Springfield which is recognized as the birthplace of Route 66 since on April 30, 1926, officials in Springfield proposed the name for the new Chicago-to-Los Angeles Highway.


Day Six

Resort: Oklahoma »
Hotel: Best Western Plus Tulsa Inn & Suites »

Leave Missouri behind today and drive toward historic Oklahoma. On the way there, visit Dale’s Ole ‘66’ Barber Shop on the corner of Utica St. and Euclid Ave in Joplin for a real bit of nostalgia. Continue your journey to Tulsa. By the 1920’s, Tulsa was a boomtown and dubbed by many as the ‘Oil Capital of the World’. Business is still booming with a thriving aerospace industry and several major corporations situated here.


Day Seven

Resort: Oklahoma »
Hotel: Fifth Season Inn & Suites »

Depart Tulsa this morning and drive toward the Oklahoma’s state capital, Oklahoma City. It is at heart a cowboy town and this can be seen at Stockyards City. It was founded in 1910 and is popular for its restaurants and shops specializing in Western wear, custom-made boots, and saddles.

Day Eight

Resort: Amarillo »
Hotel: Fifth Season Inn & Suites »

Leave Oklahoma City behind and drive toward the Lone Star State today. As you head into Amarillo make a stop in the town of Shamrock to visit the U-Drop-Inn Restaurant and Service Station dating from 1936 and the Pioneer West Museum, located in the historic Reynolds Hotel, for a glimpse on how life was in these parts when Route 66 was indeed the Mother Road. Continue to Amarillo. The combination of the railroad and ranch land has made Amarillo a cattle-shipping capital.


Day Nine

Resort: Albuquerque »
Hotel: Navito Lodge »

Leave Big Texas behind as you drive into the southwestern charm of New Mexico. First on this road you will encounter the town of Tucumcari. Continue to Albuquerque for a two-night stay. Albuquerque is New Mexico’s largest city and a study in contrasts: old and new, natural beauty and man-made wonders, frontier town and sophisticated metropolis.

Day Ten

Resort: Albuquerque »
Hotel: Navito Lodge »

On your second day take a short drive to neighbouring Santa Fe, the oldest capital city in the United States. Flanked by crooked streets and Pueblo style buildings, Santa Fe has an old world feel with a central plaza where you will find many shops, restaurants, and art galleries. Santa Fe is known as the ‘City Different’ because of the blending of cultures which is reflected in the harmonious inhabitants and different architectural styles.

Day Eleven

Resort: Flagstaff »
Hotel: Howard Johnson by Wyndham Holbrook »

Depart Albuquerque via Gallup. This small town’s two known Route 66 landmarks were lost to fire in past years; all that remains is the actual road. Press on into Arizona. Holbrook, Arizona became a frontier town in 1881 and it has remained so ever since, only the theme has changed. Historic Route 66 provided a means for those seeking better futures after World War II. Close by are the ancient Native American lands of the Navajo and Hopi Indian Nations.

Day Twelve

Resort: Flagstaff »
Hotel: GreenTree Inn Flagstaff »

This morning depart for Grand Canyon National Park which is located close to this route on the way to Flagstaff. On the way, the town of Winslow offers the Old Trails Museum and the Minnetonka Trading Post whose façade is made of petrified wood. Continue to the Grand Canyon. The overwhelming size and brilliant colours of the Grand Canyon easily make it one of the natural wonders of the world.

Day Thirteen

Resort: Las Vegas »
Hotel: The Mardi Gras Hotel & Casino »

Leave the natural wonder of the Grand Canyon behind as you drive toward Las Vegas this morning. Even though, Las Vegas and the state of Nevada do not form part of this historic route, it is such an impressive highlight that is worth the deviation. Las Vegas has something to offer everyone. From the outrageous live shows to the excitement of casinos, the action never stops from morning to night. Stroll down Las Vegas Boulevard, also known as ‘the strip’.

Day Fourteen

Resort: Los Angeles »
Hotel: Hotel Carmel Santa Monica »

Leave the glitz of Las Vegas behind and drive toward Santa Monica where you will enjoy a two-night stay. To continue following Route 66 you have to drive via Barstow for a visit to Casa Del Desierto (Desert House). This restored Harvey House houses the Route 66 Museum. After a brief stop, continue to Santa Monica.

Day Fifteen

Resort: Los Angeles »
Hotel: Hotel Carmel Santa Monica »

On your second day, spend some time at the beach; with 3.5 miles of Southern California beaches and over 300 days of sunshine, the Santa Monica Beach is a welcome retreat for vacationers and locals alike with a range of activities for everyone. Swimming, surfing, volleyball, skating, and biking are among the favourite beach-side pastimes of this area.

Day Sixteen

Resort: Los Angeles »

Depart at leisure to Los Angeles International Airport (LAX).

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