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The Mother Road is a true thrill ride. America’s most iconic highway meanders from downtown Chicago all the way to the Santa Monica Pier in California offering dozens of scenic vistas, kitschy roadside nostalgia and intimate encounters with small town America along the way. But having driven every inch of this scenic stretch of pavement, we can promise youthat at the end of each long day you’ll want a good place to rest your head. Small motels still abound, but if you’re looking for something spiffier, here are the best Route 66 hotels.

Also: The most kitschy attractions on Route 66.

Chicago Athletic Association: Chicago, IL
You’ll want a good night’s sleep before your first day on the road and this recently restored Gothic masterpiece is a true Windy City icon. Located just a literal stone’s throw from the Route 66 starting point on Adams Street between Wabash and Michigan Avenues, the Chicago Athletic Association  oozes vintage clubby cool including a lobby where you’ll want to spend hours chilling, a rowdy fun rec room featuring pool tables and shuffleboard and gorgeous city views from City’s Rooftop. Did we mention there’s a Shake Shack in the lobby?

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Magnolia Hotel: Saint Louis, MO
Much of the Gateway City has long since torn down or bulldozed over its original Route 66 diners, motels and vintage signage, but the Magnolia Hotel is in a historic building right off the route that in previous incarnations was famous for employing St. Louie’s first female general manager and also originating the concept of chocolates on pillows. Today it’s a genuine beauty where the lobby is aflutter with activity on weekends and whose rooms exude a style that is chic and minimal but also warm and inviting.

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The Mayo Hotel: Tulsa, OK
The Sooner State takes its role in Route 66 history quite seriously and this includes all kinds of treasures including museums devoted to the Mother Road, quirky diners like ballyhooed POPS and the grand and opulent Mayo Hotel, a downtown treasure located a mere five blocks from where 66 cuts a beeline through the heart of the city. We love the historic facade, opulent lobby and the affordable suites which resemble lavish one-bedroom apartments. Do yourself a favor and hit up onsite cafe Topeca Coffee before hitting the road.

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El Rey Inn: Santa Fe, NM
We love this sprawling Southwest-style charmer built smack on an original stretch of old Route 66. Its five acres of land features fountains, pathways and spacious parking, but the El Rey Inn is also affordable, unfussy and unpretentious, while still cozy, comfy and especially enjoyable during those chilly mountain nights thanks to fireplaces in several of the hotel’s 86 rooms and an onsite hot tub cabana for all. Rooms are simple and charming and the ample continental breakfast provides the necessary fuel for a long day on the road.

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Little America: Flagstaff, AZ
Flagstaff is a funky cool Mother Road stopping point and the perfect gateway for further explorations such as the Grand Canyon or the Petrified National Forest. If you’re looking for something different, consider the rustic charms of Little America, a woodsy haven set among 500 acres of Ponderosa Pine Forest not far from the interstate. While room decor tilts toward the antiquated, a night’s stay is easy on the wallet and if little ones are in tow they’ll love the outdoor swimming pool and ample elbow room for twirling themselves silly.

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Shore Hotel: Los Angeles, CA
Trust us when we tell you that by the time you reach the historic Route 66 end point at the Santa Monica Pier in Los Angeles you’ll have been on the road for at least one week—maybe even longer—and in desperate need of luxury and relaxation. You’ll find both at the gorgeous Shore Hotel, a seaside retreat and upscale boutique hotel that is offers stunning ocean views and brightly colored eco-chic guestrooms. The hotel is just steps from the Third Street Promenade which means zillions of shops and restaurants right at your doorstep.

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Tagged: California, Hotels, Uncategorized

Note: Orbitz compensates authors for their writings appearing on this site.

Jason Heidemann

Jason Heidemann

Jason is a Lead Content Specialist for Expedia Group, and manages content initiatives across numerous Expedia-owned brands. His work has been featured in the Chicago Tribune, Time Out, the Huffington Post, Chicago Magazine, Passport and many others.

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