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Hollywood’s Road Trip: Where to Stay Along America’s Most Cinematic Highway
As Route 66 rings in its 100th anniversary, we’re rounding up the best places to lodge from Santa Monica to Chicago.
By Erin Lassner
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Erin Lassner
E-Commerce Writer
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June 10, 2026 1:32pm
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Hilton Santa Fe Historic Plaza. Courtesy of Hilton
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It’s official: The U.S. is entering a road trip renaissance. According to a recent study, 71 percent of Americans plan to drive on their next vacation, and nearly two-thirds say they won’t go more than five hours without stopping at a hotel.
To ring in the return of the road trip and, coincidentally, the 100th anniversary of Route 66, we’re breaking down five key stops from Chicago — just steps from the highway’s official Adams Street start sign — to Santa Monica, the western terminus of Route 66. Since all the listed hotels are Hilton properties, guests can rack up points — and perks — at each stop through the free-to-join Honors Program (more on this below). New members can join now to earn 3,000 Bonus Points on their first three stays.
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American Road Trip: Best Hotels on Route 66
Chicago, Illinois: Hilton Chicago
Courtesy of Hilton
Kick off (or wrap up) your road trip at Hilton Chicago, steps away from the official starting point of Historic Route 66. The 1,544-room hotel sits in the Windy City’s most prime location, with sweeping views of Grant Park, Lake Michigan and Museum Campus.
When we think of this property, its rich history immediately comes to mind. In fact, the building was constructed in 1927, just one year after Route 66 was established. Since Hilton Chicago (originally the Stevens Hotel) first opened its doors as the largest hotel in the world, the landmark has been meticulously redesigned and restored to preserve its early 20th Century identity while also offering bright, modern rooms, exceptional dining options and a full menu of amenities.
Visit the Hilton Chicago’s website for current pricing, offers and a full amenity breakdown.
Tulsa, Oklahoma: Tulsa Club Hotel, Curio Collection by Hilton
Courtesy of Hilton
Keeping on theme with an equally storied property, Hilton’s 96-room downtown escape is in the ultra-chic Tulsa Club Building, an Art Deco landmark built in 1927. Reimagined as a boutique hotel in 2019, the Tulsa Club Hotel maintains its old-school charm and Art Deco identity with a glamorous design and speakeasy-style lounge. Amenities include a fitness center, on-site restaurant, room service and meeting rooms.
Visit the hotel’s website for current pricing, offers and a full amenity breakdown.
Santa Fe, New Mexico: Hilton Santa Fe Historic Plaza
Courtesy of Hilton
Getting more historic by the moment, Hilton’s Santa Fe oasis is housed in a 350-year-old hacienda. Mirroring all the magic of New Mexico’s capital city, the hotel features traditional Southwest details throughout, from an outdoor kiva fireplace to warm wood beams and rich patterned rugs. It serves as a beautiful contrast to the Tulsa Club Hotel.
Visit Hilton Santa Fe’s website for current pricing, offers and a full amenity breakdown.
Flagstaff, Arizona: DoubleTree by Hilton Flagstaff
Courtesy of Hilton
Sitting directly on Old Route 66, DoubleTree by Hilton Flagstaff is located just 10 miles from Arizona Snowbowl and within an hour and a half of Grand Canyon National Park. The hotel offers a 24-hour fitness center, outdoor pool area for warmer months, jacuzzi and indoor whirlpool for year-round usage and seasonally-inspired dining options — from southwestern cuisine to American fusion favorites. As always, Hilton’s signature plush bedding is to be expected.
Visit the hotel’s website for current pricing, offers and a full amenity breakdown.
Santa Monica, California: Hilton Santa Monica Hotel & Suites
Courtesy of Hilton
Bring it on home with the Hilton Santa Monica, located just three blocks from the ocean and world-famous Santa Monica Pier. The full-service hotel embraces the city’s breezy atmosphere, with its bright and beachy decor, outdoor cabanas, farm-to-table food and signature craft cocktails. Rooms are spacious and inviting with fresh white linens, light wood accents and California-cool furniture and accessories.
Visit the Hilton Santa Monica’s website for current pricing, offers and a full amenity breakdown.
Finally, to get the most out of your stay (and future stays), Hilton’s free-to-join Honors Program is a no-brainer. As a tiered membership model, perks range from digital keys, free Wi-Fi and late checkout to room upgrades, food and beverage credits, discounted rates and free nights — the more you stay, the more you earn. (Join now to earn 3,000 Bonus Points on your first three stays.) Membership status aside, customers can count on Hilton’s premium service at each stop. Nightly rates vary by season and room type; visit Hilton.com for the latest.
Related: Hilton Fills Hotel Gap in L.A.’s Stadium District With New Boutique Property Steps From SoFi
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