Route 66’s Major Cities and Where to Stay in Them

Route 66 begins in Chicago, but the exact spot has changed over the years. Today you’ll find the markers on East Adams Street, to the west of South Michigan Avenue, but the original starting point was the intersection of Jackson Boulevard and Michigan Avenue. For a historic stay in town, consider the Alise Chicago, housed in a landmark 1895 building. The hotel’s decor reflects its roots with wood paneling, wrought iron, mosaic tiling, and marble stairs. Be aware that since this building is over 120 years old, the rooms are small. It’s conveniently located only five blocks away from the current Route 66 starting point.

Louis and Clark famously embarked upon their voyage west from St. Louis, with the start of their trail marked by the Gateway Arch. They paved the way for thousands to travel west along Route 66 more than 100 years before the highway was built. Stay at the Hotel Majestic St. Louis to get your fill of history. Built in 1913, the hotel still retains a classic atmosphere, most notably in its Mahogany Grille, which is, of course, clad in mahogany. Road trippers should note there’s a fee for valet parking. Those looking for a driving break while they’re sightseeing in the area might appreciate the free hotel shuttle that takes you anywhere within a three-mile radius.

After crossing Oklahoma and Texas, drivers will find themselves in the scenic deserts of New Mexico. For art lovers, there’s no better destination than Santa Fe -- it’s been a hot spot for artists for decades, including, most notably, Georgia O’Keeffe. Travelers can check into the oldest hotel in Santa Fe, La Fonda on the Plaza, built in 1922 (though there’s been an inn on the property since the 16th century). Drivers can use a stay at La Fonda to stretch their legs -- many of the city’s main attractions are within walking distance. If you do make a stop here, make sure not to miss our culture vulture’s guide to Santa Fe.

If you’d prefer to check out another city in New Mexico, Route 66 runs through Albuquerque as well. Perhaps most recently famous for being the setting of the TV show “Breaking Bad,” the city offers visitors attractions like the New Mexico Museum of Natural History and the Indian Pueblo Cultural Center, not to mention great hiking just outside the city. Travelers should make the Hotel Andaluz their home base for a historic stay. Conrad Hilton -- yes, THAT Hilton -- built the hotel in the 1930s, and today it has Gold LEED-certification.

The next state in the lineup is Arizona, and Route 66 passes through the city of Flagstaff, which many travelers use as a jumping off point to visit the Grand Canyon, only a 1.5-hour drive away. A must-see in the city itself is the Lowell Observatory, where Clyde Tombaugh discovered pluto in 1930. Though not nearly as old as the other properties on our list, the Little America Hotel offers guests old-fashioned rustic charm at its 500-acre wooded property. There’s a two-mile hiking trail on-site, which is great for fresh air and exercise on a long road trip.

Route 66 officially ends at the iconic Santa Monica Pier, so where better to stay in the seaside city than on the beach? The Hotel Casa del Mar is only one of two hotels that actually has beachfront property. The landmark lodging was originally built as a beach club in 1907 and went through several changes in ownership before being converted into a hotel in the 1990s. Its most recent renovation was completed in 2015 under legendary designer Michael S. Smith.


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