
Sep 8, 20202 min read
Rent a tiny home and a Mini car from $1 per night on this open-road fall getaway
The Classen Inn, a retro-mod motel in Oklahoma City. Visit OKC
One of the world’s best-known road trips, Route 66 stretches nearly 2500 miles between Chicago and California on an epic journey through eight states that perfectly bottles up the American experience, from towering skyscrapers to swaths of empty prairie. In 2026, the "Main Street of America" is marking major mileage on its odometer, as it clocks a century since its creation in 1926.
Road tripping on Route 66 is the best way to get to the heart and spirit of the USA. It means cruising through big cities, stopping at kooky roadside attractions and oddball small towns, and gorging yourself on burgers and shakes at vinyl-clad diners. But an underappreciated aspect of this drive is staying at the charming motels and historic hotels along the way. These unique properties aren’t just cool places to lie your head after a big day of driving – they make the journey even more memorable and might just encourage you to linger a little longer. Here are the best places to bed down on Route 66.
Route 66 starts its westbound journey in Chicago and winds southwest through quirky towns and attractions hemmed in by forest and farmland. After about 300 miles in Illinois, it crosses the state line into Missouri at the mighty Mississippi River.
An opulent 1925 hotel still shines brightly
Price rating: $$$
Saunter into history in Chicago’s downtown Loop at Palmer House, one of the country’s longest continually operating hotels. Its story long predates Route 66, and the original structure was actually lost in the Great Chicago Fire of 1871. The current iteration opened in 1925. Hotel lobbies don’t get much more decadent than Palmer House, dripping with gold-dipped chandeliers designed by Louis Comfort Tiffany and capped with 21 colorfully painted ceiling frescoes in a style meant to evoke a European drawing room.
Outside, the Route 66: Begin sign – a required selfie before you start your road trip – is just a block away, beyond which lie some of the Windy City’s best things to do, including the Art Institute of Chicago and Millennium Park, lapped by the shores of Lake Michigan. The brownie was invented at Palmer House for the 1893 Chicago World's Fair, and one of these decadent treats, still made using the original recipe, makes a good snack for the road ahead.
After bridging the Mississippi, Route 66 in Missouri sets off from St Louis, heading southwest toward Kansas along the edge of the hilly Ozarks. Sadly, some vintage Missouri motels have closed recently, including the famous Munger Moss in Lebanon (it’s still worth stopping for a photo with the neon sign), but there are rumors of its return.
The indoor swimming pool at 21c Museum Hotel in St Louis. 21c Museum Hotels
History turns hip in these art-filled digs
Price rating: $$$$
Built in the 1920s as a YMCA, this downtown St Louis building reopened its doors a century later as the glam 21c Museum Hotel. It takes the museum part of its name seriously – a 24/7 art gallery on the 2nd floor, partly in the gym’s old basketball court encircled by a mezzanine jogging track, is hung with dozens of pieces from rotating exhibitions and takes up more than 14,000 sq ft. The creativity expands to every part of the property, including the hotel’s 173 plush rooms, which are decorated with works by artists with ties to Missouri.
Retro motor court goes modern
Price rating: $$
"Elvis stayed here!" blazes on the sign of the Best Western Route 66 Rail Haven in Springfield, which calls itself the "birthplace of Route 66" because it’s where the highway’s name was officially decided. This motel opened in 1938 and has been well-maintained ever since. The bones of the building – a one-story structure where you can drive right up to your door – remain in place, but the interiors have been thoughtfully updated.
It’s worth shelling out a little extra for one of the themed suites, such as the Elvis Suite, with a pink Cadillac bumper as the bed’s footboard, or the "Wild Bill" Hickok Room, with a pressed-tin ceiling, oversized copper tub and a mural depicting an 1865 shootout between Hickok and a local gambler on Springfield’s downtown square. Now at that location is the engaging History Museum on the Square, which houses the Rail Haven’s original neon sign and the telegram that named Route 66.
Vintage vibes in a 1930s architectural gem
Price rating: $$
One of Missouri’s most atmospheric Route 66 motels is in the small town of Carthage, a short jaunt from the Kansas border. Boots Court opened in 1939 and was built in the gorgeous Streamline Moderne style, a variation of art deco with rounded corners and long horizontal lines. At night, the place glows with green and red neon reflecting off the whitewashed facade. A sign out front still advertises "a radio in every room," and staff make sure it’s turned on when you squeeze your vehicle into your personal historic covered carport.
After a brief 13 miles in Kansas, the road hits Oklahoma, which in many ways feels like the heart of Route 66, with gloriously long stretches of original pavement along its 400 miles. Author John Steinbeck wrote about Oklahomans escaping the Dust Bowl along Route 66 in The Grapes of Wrath, giving it the nickname the Mother Road.
Luxe revival of Tulsa’s art deco downtown
Price rating: $$$
When the Mayo Hotel, once Oklahoma's tallest building, opened in 1925, it was the height of luxury, and it's one of Tulsa's top stays after being saved from demolition and revitalized to its former glory. Tulsa had millions of dollars pumped into the city in the early 1900s after oil was discovered nearby, resulting in a strikingly beautiful downtown filled with art deco jewels as newly minted millionaires tried to out-build one another. Route 66 runs along the southern edge of downtown, so hop out of the car to stretch your legs on a guided art deco adventure with Tulsa Tours, which has the keys to otherwise inaccessible 1920s interiors.
Good-value motel with a big personality
Price rating: $
The well-priced mid-century Classen Inn near downtown OKC has had a mod makeover and now shows off its groovy 1960s attitude through bold palm tree wallpaper and custom murals painted in navy blue, burnt orange and olive. Though the motel doesn’t have many amenities, rooms can be under $100 a night, a brilliant find for a major metropolis.
Feel like a million bucks at this bank-turned-hotel
Price rating: $$$$
A jaw-dropping historic stay in OKC is The National, a 1930s bank that reopened as a luxury hotel in 2022. Have a drink in the gasp-worthy lobby bar in the former banking hall with nearly 100-year-old marble floors, columns and huge murals. If darkened drinking dens are more your thing, the hotel also runs a bar downstairs in the old bank vault. The rooms are sleek and modern, and the windows in some corridors open onto the Great Hall from a height. The National is set in downtown, at the heart of the Oklahoma capital, so it’s easy to get to local attractions and Route 66.
Route 66 runs through a lesser-visited part of Texas, covering about 200 miles through the dusty Panhandle Plains.
Overnight in a Conestoga wagon in cowboy country
Price rating: $$
The days of wagon trains and cattle drives were history by the time Route 66 rolled around, but you can still make like a traveler of yore by staying the night in a Conestoga wagon in Amarillo, about halfway between Chicago and Los Angeles on Route 66 and the biggest urban expanse since Oklahoma City. The Big Texan is a kitschy institution in this cowtown, advertising free 72oz steaks (if you can eat the ginormous portion plus a bunch of sides in under an hour; otherwise, it’s $72). Besides the restaurant, it runs several accommodation options. You don’t need your own rig to stay the night at its RV park if you opt for one of the Old West wagons, and unlike the pre-66 pioneers, you can enjoy heating and AC, plus your own keypad-accessible bathroom a few steps away.
Route 66 through New Mexico dials up the scenery big time, with 535 miles of road through scrub-speckled deserts, steep mountain passes and beautifully layered mesas. A branch of Route 66 bypassing Santa Fe opened in 1937, and even though it makes the journey shorter, don’t you dare take it – the charming adobe capital city is one of the best places to visit in New Mexico.
The standard bearer of vintage Route 66 motels
Price rating: $
Perhaps the most legendary historic motor court on Route 66, the Blue Swallow Motel retains every bit of charm that it was originally built with. Opened in 1940, this motel has changed little since, in the best way possible. Its still-glowing neon sign promises 100% refrigerated air, and each room has its own garage, which you can pull your car into – as long as it’s the same size as a 1939 Ford Deluxe. It’s cared for by friendly owners who show you around the 14-room property when you check in.
Hip heritage in a historic building
Price rating: $$
Opened in 1936, El Rey Court is a classic property right on the Route 66 roadside southwest of downtown Santa Fe. It’s done up in Southwestern mid-mod decor, with adobe walls, terra cotta floor tiles and art unique to each of its 86 rooms, some of which even have kitchens and kiva-style fireplaces. Ask for a room in the historic building for maximum charm. The motel’s program of live music, queer nights and tarot card readings draws in locals in addition to Route 66 road trippers and other travelers, and the food truck parked outside the bar ensures everyone lingers a while.
Roadside motel redone for modern travelers
Price rating: $$
Thoroughly reimagined but still retaining its vintage magic, El Vado Motel is a gem of ABQ’s Route 66 motels. Revamped in 2018, some of the rooms of this 1930s motel have been converted into boutique shops and small-scale eateries, visitable even if you end up staying elsewhere. The motel also has an on-site brewery and a swimming pool in the central courtyard, perfect for whiling the evening away.
Stay like a star of the Old West
Price rating: $$
Established in 1881 with the arrival of the railroad, Gallup still sees miles-long freight trains chugging past Route 66, which parallels the tracks and is lined with trading posts selling Navajo-made silver jewelry and other souvenirs. This sleepy town doesn’t feel like it’s changed much in decades, and that’s even reflected in the best place to stay in Gallup, El Rancho. Movie stars acting in locally shot westerns and early Route 66 drivers were the first to stay in this 1937 hotel. Its maximalist lobby feels like a Southwestern-style hunting lodge, oriented toward a fireplace with two curving sets of stairs. The rooms are named after Hollywood legends and are atmospherically outfitted with Western decor.
Route 66 in Arizona is a road trip into the natural – and the supernatural. It’s worth dedicating a good chunk of time to this state to stop and explore two national parks (Grand Canyon and Petrified Forest), even more national monuments and cosmic wonders like a massive meteor crater and the world’s first International Dark Sky City.
Historic Harvey House still welcoming train riders and Route 66 drivers
Price rating: $$$
History runs deep at the beautiful La Posada, the final grand railway hotel from the Fred Harvey Company, which opened hotels and eateries along the Santa Fe Railway and is credited with being the first restaurant chain in the country. Opened in 1930 and rescued from demolition six decades later, this hotel is right on Route 66 and also still serves as the town’s Amtrak station, with Adirondack chairs set up near the platform for train spotters to watch them go by.
Explore the historic structure and among the elegant tilework, glass chandeliers and Navajo rugs, you’ll uncover an art gallery with works by one of the preservation-minded artist-owners and a museum detailing the history of the building, its female architect – a rarity at the time – and Fred Harvey’s legacy. A meal at the Turquoise Room, the hotel’s on-site restaurant, might be the best thing you’ve eaten in several hundred miles. Don’t miss the stuffed squash blossoms or the lamb sampler, with meat raised on Navajo Nation land served three ways.
Where Route 66 meets the Space Age
Price rating: $$
Is there a groovier place on Route 66 than the Americana Motor Hotel? The 1960s and ‘70s are alive at this glammed-up motel with in-room disco balls that start spinning with the push of a button, faux wood-paneled walls, and on-point navy blue and burnt orange carpet. Keep the fun spirit going with outdoor lawn games and a swim in the heated pool. Other amenities include rentable telescopes for stargazing and bicycles if you want to cruise the couple of miles into downtown Flagstaff.
Trailborn Grand Canyon.
Recently opened Route 66 motel near an iconic national park
Price rating: $$
Route 66 runs right through tiny Williams, a gateway town to the South Rim of the Grand Canyon. Its accommodation scene got a major boost this year with the opening of Trailborn Grand Canyon, a boutique spot in a revamped two-story 1960s Route 66 lodge. The cozy Southwestern decor roots travelers in place, and amenities like s’mores kits and an outdoor fireplace might make you stay up past your bedtime. The on-site Miss Kitty’s restaurant is a dinner-only steakhouse and one of the finest dining options in town. Pull up a stool at the bar backed by turquoise tiles and sip on an All-American Old Fashioned, mixed with bourbon and Dr Pepper. The hotel is a short distance from the Grand Canyon Railway, which delivers you right to the South Rim.
The last 315 miles of Route 66 squeeze in a final stretch of lonely desert in California before crashing into the ever-expanding suburbs of Los Angeles. Before you know it, you’re at the end of the continent and the end of the drive.
Overnight in a cozy cone
Price rating: $
In the 1930s, a chain of "wigwam" motels with rooms inside 32ft-tall concrete tipis started opening across the country. Today, only three survive, and two are on Route 66 – they are the inspiration for the Cozy Cone Motel in Cars. The last of the bunch, opened in 1949, was the Wigwam Motel in San Bernardino, whose 19 structures form a horseshoe shape around a central kidney-shaped pool. The furnishings don’t look like they’ve been updated much since the property opened, but they are clean, and it’s a kitschy, friendly place to stay.
Chilled-out spot just before LA proper
Price rating: $$$
Pasadena Hotel & Pool was built the same year as Route 66, but reopened in 2022 after extensive upgrades, and road-weary travelers still kick back in the oversized rooms and the rooftop pool with views of the San Gabriel Mountains. The lobby feels like a cool coworking space that transitions from a chat-filled breakfast nook by day to a sleek post-work bar by night. It’s a great place to stay if you crave the urban vibe but don’t want to deal with LA traffic.
Celebrate in style at the Route 66 finish line
Price rating: $$$$
Cap off your Route 66 road trip with a luxe stay at the Fairmont Miramar, built on the site of the private estate of US Senator John Jones, who founded Santa Monica. It’s a short distance from the beach and the Route 66: End of the Trail sign on Santa Monica Pier. Some of the plush hotel rooms have beach views, but the bungalows near the pool feel much more homey – if you didn’t have a suitcase, you might think you live here. Before you start the drive back home after your Route 66 road trip, grab breakfast at Fig, the hotel’s poolside restaurant that sources many of its ingredients from local farmers markets.