Unique Places to Stay Along Route 66

Part of the fun of road tripping Route 66 is figuring out where to stay. Just imagine driving all day and pulling up to a cool motel with a bright neon sign advertising a room vacancy. Or maybe it’s a historic inn with stories that predate Mother Road herself. Either way, as a big fan of unique hotels (if you know, you know ;)), I very much loved learning about the cool places to stay from Chicago, IL all the way down to Santa Monica, CA.

Check below for where you can stay!

Where to Stay on Route 66

Illinois

Palmer House in Chicago

Begin your trip on the fancier end with a stay at the Palmer House right near the start of Route 66 in Chicago. The hotel goes back to 1870 and was built as a wedding gift from wealthy businessman Potter Palmer for his wife, Bertha Honoré! As one of the longest running hotels in the US, it’s seen everyone from Charles Dickens to The Supremes, and just recently underwent a massive renovation to bring it back to its historic glory. Even if you don’t wind up staying here, take a moment to step into the lobby and marvel at its opulent interior! Also ask about trying one of their brownies. They did, after all, invent them!

Arcadia in Mclean

Further down Route 66 in Illinois is a town that feels like a step back into the 1980s. When it comes to McLean, the focus is all about arcade games! Every single building has some sort of game you can play, and, of course, there are multiple arcade-themed places to stay. Hotel Arcadia is a fun apartment that includes four arcade games, a pinball machine, and more. And then for bigger groups, Vectorman’s Luxury Arcade Palace and Hotel Arcadia Suites have more space and arcade games!

Missouri

Union Station Hotel in St. Louis

Another historic hotel to add to your list! Like the name suggests, Union Station was once a massive train station for St. Louis with grand designs like its Romanesque Grand Hall and stained-glass windows. Even now as a hotel it retains its beautiful decor! When you check in, ask about the Grand Hall Light Show.

The Wagon Wheel Motel in Cuba

The oldest continuously operating motel along Route 66 and alleged inspiration for the Wheel Well Motel in Cars, The Wagon Wheel has been welcoming roadtrippers since 1936! The stone buildings come from Ozark stone and to this day they still have their same wood doors, hardwood floors, and neon sign.

Shamrock Court in Sullivan

Between St. Louis and Springfield, Shamrock Court is a newly opened and renovated motel that goes back to the 1940s. It lay closed for the better part of the last decade until couple Roamin and Christina Dinkela purchased it in 2021 and completely revitalized it right down to its gorgeous neon design! Make your stay extra fun and book their Neon Room!

Rockwood Motor Court in Springfield

As the birthplace of Route 66, Springfield, MO has no shortage of iconic hotels whether you want something more boutique like Hotel Vandivort or you want to fully lean into the kitsch at Best Western Route 66 Rail Haven. I personally love the design of Rockwood Motor Court, which is considered the oldest operating court on the highway. It was built back in 1929 and includes six cabins, a filling station, and a nice outdoor space to grill and relax.

Boots Court in Carthage

Down in Carthage, you can’t miss the neon green glow of Boots Court come night time. This is yet another roadside motel that was built during the heyday of Route 66, and has managed to survive to see its centennial! Its original owner, Arthur Boots, designed it in the Steamline Moderne style and apparently charged quite a large amount to keep away “unsavory guests.” The price? $2.50 a night!

Oklahoma

The Campbell Hotel in Tulsa

Where to stay in one of the coolest cities on Route 66? The Campbell Hotel, of course! Built back in 1927 as the Casa Loma Hotel, it was nicely located outside of Tulsa’s more expensive downtown but at the end of a trolley line that could take them right into the thick of things. Its design is Spanish Colonial Revival and each of the 26 rooms have their own themes like Art Deco or Leon Russell.

Classen Inn in Oklahoma City

Over in Oklahoma City, stay in a hotel known for its Googie architecture, The Classen Inn. Once you’ve seen one of these midcentury futuristic designs, you’ll know exactly what I mean when I say “Googie”! Built in 1963, the inn is a huge pop of color and patterns and is located just a few blocks from midtown. They also have a very fun Superette onsite, aka their take on a convenience store.

Texas

The Big Texan in Amarillo

What’s better than a massive restaurant that has a 72oz Steak Challenge? A restaurant that offers you accommodation in case you indulge a little too much. The Big Texan in Amarillo has multiple lodging options – including wagons!

Dove Rest Canyons in Amarillo

After you’ve had a chance to join the Cowgirls and Cowboys in the West and ride a horse around Palo Duro Canyon, book a stay in one of their Dove Rest Cabins. Each cabin is private and will have some absolutely breathtaking views of the canyon!

New Mexico

Inn of Five Graces in Santa Fe

One of my absolutely favorite hotels, the Inn of Five Graces is still one of the most unique places I’ve ever been. Every single part of this hotel is completely handmade right down to the wooden doors and mosaic designs. It’s also located in the Barrio de Analco of Santa Fe, aka the oldest neighborhood in the United States.

Motel Safari in Tucumari

When you enter New Mexico, stop off in Tucumari, somewhat of a desert oasis along Route 66. Stay at Motel Safari for more of that cool, Googie style. The motel has been around since 1959 and still has many of those retro futuristic designs.

ARRIVE Alburquerque

If Wes Anderson designed a hotel, I have to imagine it would look pretty similar to ARRIVE Alburquerque. Right on Central Ave, it first opened as The Downtowner in 1965 then turned into Hotel Blue before sitting empty until it was renovated and reopened in 2025. The rooms are also beautifully designed like a cross between Midcentury Southwestern and your grandma’s coziest room!

Arizona

La Posada Hotel in Winslow

La Posada Hotel packs multiple historic punches for a hotel located in such a tiny town on Route 66! The first is that it’s one of the last of the Fred Harvey railroad hotels. Back in the day Harvey hotels were some of the finest places you could stay in while traveling by train. La Posada still has a station for Amtrak passengers right in its backyard. The second punch is that the hotel was designed by renowned American architect, Mary E.J. Colter, one of the few female architects in the 1920s and 30s. And the third punch is that it was bought and completely renovated by Allan Affeldt and artist Tina Mion, who has an entire gallery on the second floor. When staying, grab a bite at The Turquoise Room, their beautiful onsite restaurant.

Wigwam Motel in Holbrook

The Wigwam Motel is the first of two that you can stay in on Route 66. This one is in Holbrook and lets you stay in one of the teepee rooms (because, yes, they’re teepees not wigwams!).

Aztec Motel in Seligman

Seligman is known as the inspiration for Cars, and it’s home to, quite literally, the angel of Route 66, Angel Delgadillo! Stay overnight in the cozy Aztec Motel right across the street from his store. They’ve got a great creative space where you can meet other guests or unwind after a day of driving. Be sure to say hello to their resident cat, Ms. Frankie Chica Cheekers while you’re there.

Americana Motor Hotel in Flagstaff

Over in Flagstaff, The Americana Motor Hotel feels like a modern take on the retro motor court designs! Think retro futurism but with astronomy artwork mixed in. Disco balls in your room and multicolored lights to greet you as you pull in. Let me just say, my crew and I took our rest day at this hotel, and we all left absolutely loving it!

California

Pasadena Hotel & Pool in Pasadena

Nearing the end of your Route 66 journey! Pasadena Hotel & Pool was built all the way back in 1926 by local businesswoman (yes, woman), Constance V.L. Perry. It has that Mediterranean exterior SoCal is known for, and the interiors have been renovated to pay homage to its Roaring Twenties origin.

Wigwam Hotel in San Bernardino

The next teepee you can stay in is at the Wigwam Hotel in San Bernardino. All the teepees sit in a semicircle right off Route 66, and there’s even a little kidney bean pool you can cool off in at the center!

Regent Santa Monica in Santa Monica

If you really want to end your Route 66 journey with a bang, splurge on a night at the very luxurious Regent Santa Monica. Located right on the beach within walking distance of the boardwalk, it really might be one of the fanciest hotels I’ve ever stayed in! Rooms are elegantly decorated, and, really, the whole goal of the hotel’s design is to let you take in all the gorgeous views of Santa Monica. The coolest way to end your entire Route 66 journey is to watch the sunset right from one of their balconies!

And there you have it – unique places to stay on Route 66 from Illinois to California. Have you stayed in any of these hotels and motels? Let me know below!