First declared a federal highway in 1926, Route 66 extends 2,448 miles from Chicago to Los Angeles, serving as a 100-year-old reminder of the golden age of U.S. road trips. As the “Mother Road” celebrates her centennial in 2026, historic hotels along the route are saluting her, too.
According to Hilton's 2026 Trends Report, 71% of Americans plan to drive on their next vacation, making this the perfect time to travel the country’s storied highway and visit historic properties along the way. And while clients can obviously traverse the iconic highway in either direction, most early travelers headed from east to west, so Chicago is considered the “starting point" and Santa Monica, California, is the "End of the Trail."
The Santa Monica Pier in Los Angeles is the "End of the Trail."
Credit: 2025 Santa Monica Travel & Tourism
“The 'Mother Road' connected our city to the western United States at a time of explosive growth and development nationally,” said Rob Fojtik, vice president of Choose Chicago. “It remains an emblem of uniquely American ideals of opportunity, self-determination and exploration, which, along with the enduring appeal of the great American road trip experience, draw millions of global visitors to Route 66 every year."
Here are six historic hotels along Route 66, organized from east to west, to recommend to clients.
The Drake Hotel in Chicago
Designated a National Historic Landmark, The Drake Hotel opened in 1920 as a luxurious urban resort on Chicago’s Magnificent Mile, and has maintained that status for more than 100 years.
“The Drake Hotel has a historic connection to Route 66 through its founder's family,” said Damien McArdle, the hotel’s general manager. “John B. Drake, the hotel's namesake, was the manager of the Grand Pacific Hotel, a key establishment on the pre-Route 66 path in Chicago and part of the lineage that would eventually lead to the creation of the famous highway.”
Marilyn Monroe and Joe DiMaggio visited The Drake Hotel during their honeymoon.
Credit: 2025 The Drake HotelThe hotel’s notable spaces include the elegant Palm Court (which has hosted Queen Elizabeth and Princess Diana for afternoon tea); the Coq d’Or lounge and bar, known for its signature Bookbinders soup; and Cafe on Oak, a breakfast spot overlooking Lake Michigan where clients can order the MM+JD eggs benedict (a tribute to Marilyn Monroe and Joe DiMaggio, who carved their initials in the space during their honeymoon).
Magnolia Hotel in St. Louis
Initially opened in 1924 as the Mayfair Hotel, the 182-room Magnolia Hotel St. Louis, a Tribute Portfolio Hotel, is credited with introducing "chocolates on a pillow," thanks to Cary Grant, who requested the sweet romantic gesture. The Hollywood legend is also the inspiration for the boutique hotel’s Art Deco-style Cary Grant Suite.
The Cary Grant Suite at Magnolia Hotel St. Louis is named for the star who first requested chocolates on a pillow.
Credit: 2025 Magnolia Hotel St. LouisBarfield, Autograph Collection in Amarillo, Texas
Just 50 miles from Route 66’s official midpoint in Adrian, Texas, The Barfield, Autograph Collection is housed in the historic Barfield Building, which opened in 1927 at the intersection of Polk Street and Route 66.
The Paramount Recreation Club, the building’s original prohibition-era speakeasy, is hidden in the Barfield Hotel’s basement.
Credit: 2025 Visit AmarilloAfter being vacant for three decades — and following a $35 million renovation — the 112-room boutique hotel reopened in 2021, complete with the original 1927 revolving door and elevators. The Barfield also features The Legacy Library, a tribute to Melissa Dora Oliver-Eakle, the founder of Amarillo's first library and the building’s original developer. Oliver-Eakle’s prohibition-era speakeasy, the Paramount Recreation Club, is still hidden in the basement
Hotel St. Francis in Santa Fe
The oldest hotel in Santa Fe originally opened in 1924 as the upscale De Vargas. In 2009, the Hotel St. Francis was acquired by Heritage Hotels & Resorts, which renovated the building to pay tribute to Santa Fe’s patron saint with decor inspired by the city’s early Franciscan missionaries, including traditional sacred art, New Mexico artifacts and historical black and white photographs of the city’s early history.
The decor in Santa Fe's oldest hotel was inspired by the city's early Franciscan missionaries.
Credit: 2025 Visit Santa FeHotel St. Francis is also home to the award-winning Secreto Lounge, where clients can learn about ancient wine-making traditions introduced by Franciscan monks, or sip award-winning, hand-crafted cocktails created by Santa Fe’s top mixologist, Chris Milligan.
Arizona Biltmore
First welcoming guests soon after Route 66 began transporting travelers across the country, the Arizona Biltmore quickly became known as a glamorous stop off the Mother Road, attracting Hollywood legends such as Marilyn Monroe and Clark Gable, as well as nearly every U.S. President.
The Arizona Biltmore opened just three years after Route 66 travelers first passed through the state on their way to California.
Credit: 2025 Arizona BiltmoreFollowing a 2021 reimagination, Arizona Biltmore's Frank Lloyd Wright-influenced architecture is complemented by modern sophistication, with refreshed luxury cottages, a world-class spa and seven pools, including a family pool with a 65-foot triple water slide.
“Since 1929, Arizona Biltmore has been a touchstone of American hospitality and desert design, standing at the crossroads of storied road trips and timeless architecture,” said Michael Hoffmann, vice president and managing director for the resort. “Our restored spaces offer Route 66 travelers a meaningful connection to Arizona’s past, paired with contemporary comforts.”
Hotel Casa Del Mar in Santa Monica
Built in 1926 as a private beach club for Hollywood’s elite, Hotel Casa del Mar, one of the most glamorous luxury hotels in Los Angeles, will mark its 100th anniversary in 2026 with a full calendar of centennial moments, complementing Santa Monica’s commemoration of the Route 66 Centennial and offering advisors the rare opportunity to recommend a destination celebrating two historic milestones in one year.
Casa Del Mar is one of only two hotels located directly on Santa Monica Beach.
Credit: 2025 Hotel Casa Del Mar“As Casa del Mar approaches this historic year, we honor its legacy on the shore of the Pacific,” said Max Jonas, general manager. “Our team is creating experiences and surprises that feel both nostalgic and new, each one a celebration of the sense of timelessness that Casa evokes.”
One of only two hotels located directly on Santa Monica Beach (the other is Shutters on the Beach next door), Casa Del Mar is less than 1 mile from Route 66’s “End of the Trail” sign.
“Santa Monica is proud to be part of the legacy of Americana road-trip culture and welcomes travelers to experience a taste of this era at a landmark property that has stood throughout the Route’s history,” said Misti Kerns, president of Santa Monica Travel & Tourism. “As the city prepares to celebrate the once-in-a-lifetime milestone of this beloved piece of American history and culture, the destination is truly a breath of fresh ocean air at the end (or beginning) of the ‘Mother Road.’”
