Top 5 Destinations on Route 66 between Los Angeles and Chicago

Aug 22, 2021


Riding Route 66 on a Harley-Davidson motorcycle.

Historic Route 66 is the classic American highway. During the Dust Bowl, it served as a passage to California for those moving west to explore fresh opportunities. Now travelers from across the world make the pilgrimage down Route 66, encountering everything from ghost towns to beautiful national parks. 

Route 66’s length and stops make it incredibly popular with motorcycle enthusiasts, especially those looking to explore the terrain of the southwest. Touring Route 66 on a motorcycle is not just a bucket list item; it’s a rite of passage. 

From the Gateway Arch to the Grand Canyon, here are five of Route 66’s greatest highlights if you’re taking a road trip from Chicago to Los Angeles. You’re also welcome to start with a motorcycle rental in Los Angeles and reverse your route. 

1. The Gateway Arch — St. Louis, Missouri

Start your motorcycle trip by stopping in St. Louis, Missouri, where the famed Gateway Arch stands, otherwise known as the gateway to the west. Registering in at a staggering 630 feet, it’s considered the tallest monument in all of the United States. This monument celebrates the westward expansion of the United States, marking the spot where Lewis and Clark began their historic expedition to the American West in 1803. 

Visitors can take the tram system to the top to view this gorgeous monument and the city of St. Louis. 

St. Louis is actually the largest city between Los Angeles and Chicago on Route 66, so it’s a great place to settle for dining and an overnight stay. St. Louis also offers visitors many brochures about Route 66, including directions to the famous Route 66 State Park in Missouri. 

2. Santa Fe Plaza and La Fonda Hotel — Santa Fe, New Mexico

Hundreds of miles past the Gateway Arch is another jaw-dropping piece of American architecture, Santa Fe Plaza. A showpiece of traditional New Mexican architecture, the Plaza is home to the equally impressive La Fonda Hotel. Last year this 17th-century hotel was rated the No. 2 Hotel in the American Southwest and West by Condé Nast Traveller magazine. 

The Plaza features a central park and is surrounded by restaurants, museums, and shops. It has been the commercial and social center of Santa Fe since 1610, when Don Pedro de Peralta established the city. 

The Plaza formerly served as the endpoint of the Santa Fe Trail and El Camino Real (the Spanish royal road beginning in Mexico City, Mexico). The buildings around the Plaza are constructed in Pueblo, Spanish, and Territorial styles, reflecting the background and history of Santa Fe.

Be sure to stop here on your Route 66 road trip and enjoy some delicious Tex-Mex meals before getting back on the road. 

3. The Cadillac Ranch — Amarillo, Texas

The Cadillac Ranch in Amarillo, Texas, is arguably the most famous work of art on Route 66. Created in 1974 by artists under the instruction of Stanley Marsh 3, this art installation is composed of 10 Cadillacs driven nose-first into the ground at the same orientation as the Pyramids in Egypt! 

The Ranch is situated directly on Route 66; visitors only have to open a gate leading to the desert field where the cars are displayed. The installation is accessible free of charge.

This is an interactive art installation: visitors are encouraged to tag the cars with spray cans. (Your mark won’t last forever, as the cars are regularly repainted.) 

Along Route 66, there are also several replicas and tributes to the Cadillac Ranch. In Staunton, Illinois, Henry’s Rabbit Ranch features a similar display but with Volkswagen Golfs instead of Cadillacs. In Conway, Texas, near Amarillo, there’s a similarly-themed Volkswagen Beetles display. Stop by at least one of these classic pieces of Americana during your Route 66 road trip.

4. Grand Canyon National Park — Flagstaff and Williams, Arizona

Arizona’s Grand Canyon is an obligatory stop for Route 66 travelers. This must-see destination isn’t located directly on the route; it’s a few miles away from the towns of Flagstaff and Williams, where you can find plenty of restaurants, hotels, and tourist shops. If you’re traveling west along Route 66, entering the park through Flagstaff and Williams is simple enough.

The canyon is located within Grand Canyon National Park, which was established in February 1919. When President Theodore Roosevelt visited the Grand Canyon in 1903, he described it in glowing terms: 

“Beyond comparison—beyond description; absolutely unparalleled throughout the wide world.” “Let this great wonder of nature,” he continued, “remain as it now is.”

In 1908, Roosevelt declared the Grand Canyon a national monument. Today the park spans over 1.2 million acres and preserves some of the most striking natural beauty in the United States. No visitor will leave disappointed.

5. The Bottle Tree Ranch — Helendale, California

Last but not least, the Bottle Tree Ranch affords a fascinating stop for those interested in folk art. Located east of Helendale, California, this art installation is the personal project of an artist whose father collected bottles along Route 66. It comprises hundreds of bottles and road signs and is impossible to miss traveling down the California portion of Route 66. 

Unfortunately, the Bottle Tree Ranch is closed to visitors year-round, so you’ll have to view it from the roadside. 

With so many unique and varied destinations, it’s little wonder why Route 66 has occupied a prominent place in the national consciousness since its completion in 1928.

Once you complete your road trip from Chicago to Los Angeles, be sure to tour these amazing motorcycle rides around Los Angeles to continue your adventure.