Few things encapsulate the spirit of freedom, adventure, and independence more than Route 66, which has seized the imaginations of road trippers and romantics around the world.
The Mother Road is known for its distinctly Americana vibe, characterized by neon-lit motels, retro signage, and old-school diners. But, cutting through eight states, it also passes some of the most stunning scenery in the U.S.
This year, the iconic American highway is celebrating its 100th anniversary with events, festivals, concerts, and art installations such as the Centennial National Kick-Off in Springfield, Missouri (April 29 to May 3, 2026), and the Route 66 Road Fest in Tulsa, Oklahoma (June 27 to 28, 2026).
Planning to get your kicks on Route 66 and join the festivities this year? Luckily, the 2,448-mile route boasts plenty of stylish stays along the way. Here are some of our favorites, from Chicago to Santa Monica.
Chicago Athletic Association
The hubris of male politicians and leaders at the turn of the century is to thank for this architecturally striking hotel filled with intricate woodwork, arched windows, and mosaic-tiled floors. Inspired by the Doge’s Palace in Venice and designed in the Venetian Gothic style, Chicago Athletic Association opened in 1893 as a private club for the city’s head honchos. It remained members-only until 2007, was added to Chicago’s endangered buildings list that same year, and was turned into a 240-room hotel (part of The Unbound Collection by Hyatt) in 2015. Rooms hearken back to the hotel’s history, many with fireplaces, wrought-iron bathtubs, and original stained glass accents. There’s also an eight-seat omakase counter, a popular rooftop bar with views of Millennium Park and Lake Michigan, a game room, indoor golf simulators, and a gym. It’s been awarded one Michelin Key.
21c Museum Hotel St Louis
Housed in a 95-year-old former YMCA, 21c Museum Hotel St Louis, as the name implies, is part hotel and part contemporary art museum. In fact, its 14,000-square-foot exhibition space is partially composed of the YMCA’s original facilities, like its double-height basketball court and the running track that circles above it. The artsy theme continues in the 173 rooms, where guests can expect gallery-like high ceilings and large windows with art-covered walls, as well as custom-designed furniture and Malin+Goetz bath products. There’s also a café serving coffee, pastries, juices, and lunch and breakfast, an intimate dinner restaurant featuring Spanish fusion cuisine, a spa, a gym, and a massive (original YMCA) pool with windowed saunas that overlook it.
The Bradford House
The Bradford House, which sits on a quiet, residential street, doesn’t look like much from the outside. But on the inside, it’s an eclectic, technicolor dreamscape with bold animal prints, floral wallpaper, bright green velvet accents, pink bathtubs, and rooms painted in every shade of the rainbow. The 1912 Victorian mansion is now a 12-room hotel in which no two are the same, decorated in vintage furnishings and décor hand-collectsed by the owners in local markets and in France and Italy, with high ceilings and original tile, mirrors, and millwork. There’s also a chic little cocktail bar, a stylish restaurant serving brunch, dinner, and afternoon tea, a large wraparound porch for alfresco drinks, and an on-site pâtisserie with coffee and freshly baked pastries.
Los Poblanos Historic Inn & Organic Farm
This two-Key Michelin stay outside Albuquerque is a breath of fresh air, literally. It’s the definition of whimsical—a family-run 25-acre working lavender ranch where peacocks roam freely under centuries-old cottonwoods, and guests are encouraged to ditch their cars for complimentary cruiser bikes. Los Poblanos Historic Inn & Organic Farm was designed in the 1930s by the “father of Santa Fe style” and still radiates old-fashioned Southwestern grandeur with hand-carved ceilings, decorative Spanish tile, adobe walls, and kiva fireplaces. However, clean lines, neutral hues, and minimalist artwork modernize the space. A saltwater pool, gym, spa (with lavender-infused products aplenty), and a popular farm-to-fork restaurant that uses seasonal produce from the on-site garden make this a high-end but unfussy stay.
El Rey Court
El Rey Court perfectly toes the line between classic Southwest design and modern minimalism. Originally built in 1936, the adobe roadside motor court, set on five acres of sprawling old-growth gardens, was fully redesigned and now offers 86 bright and airy rooms with geometric art and Navajo fabrics. Common spaces ooze cool, like the vinyl library-boasting lobby, the mezcal and tequila-focused bar, and the retro striped-umbrella-lined pool with a swim-up bar.
Americana Motor Hotel
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Kitschy in the best possible way, the Americana Motor Hotel is a playfully nostalgic motel originally built in 1962 and reimagined in 2023. Describings itself as “The Jetsons meets Easy Rider,” the 88-room property sits right on Route 66 and in the world’s first Dark Sky City, meaning it offers unparalleled stargazing. Rooms are cheerful, with disco balls, faux wood-paneled walls, and retro orange and blue rugs and headboards in vibrant geometric graphics. There’s also a walk-up window serving burgers and fries, cocktails crafted by a “space-age cocktail machine,” a year-round heated pool, and a backyard with firepits, hammocks, and yard games.
Under Canvas Grand Canyon
While not exactly on Route 66, no road trip along it would be complete without a quick detour to the Grand Canyon. Under Canvas, which operates 13 properties at national parks across the country, is famous for having taken glamping to stylish new heights. Set on 160 acres of secluded piñon and juniper forest, its Grand Canyon location boasts chic safari-style tents in all sizes outfitted with plush king beds, en-suite bathrooms with organic bath products, and wood-burning stoves. Each has an airy, almost beachy-chic vibe with rattan, cognac-hued leather, and light wood accents. A restaurant tent serves up seasonal and locally sourced produce, like grilled shrimp tacos, and there’s nightly s’mores roasted over communal firepits. As a certified Dark Sky Resort, the property also offers celestial-themed meals, star parties, and astronomer-led stargazing and astrophotography experiences.
The Georgian
The teal-colored, Wes Anderson-giving Art Deco mini-skyscraper steps from the beach in Santa Monica is hard to miss. Having first opened in 1933, the hotel was the place to see and be seen: Marilyn Monroe, Clark Gable, and Charlie Chaplin all used to hang out here. During Prohibition, it was home to a lively speakeasy allegedly frequented by Al Capone and his cohorts. Despite its haughty history, The Georgian fell into disrepair (and was briefly a retirement home) until 2020, when it was purchased by the people behind various Ace and Hoxton hotels. Today, “Santa Monica’s First Lady” is back to its former glory and then some, paying homage to its former Golden Age opulence. Arched ceilings, custom Art Deco-inspired furniture, bold-hued velvet accents, and geometric-patterned wallpaper give the place a dramatic flourish, and the panache continues in common spaces like the seductive cocktail bar, the playful terrace overlooking the ocean, and the well-stocked library.