The Ultimate Route 66 Road Trip: From Illinois to California

The Ultimate Route 66 Road Trip: From Illinois to California

The Ultimate Route 66 Road Trip: From Illinois to California

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Affectionately known as “The Mother Road”, Route 66 offers the quintessential American road trip experience. Stretching from Chicago to the Santa Monica Pier, the legendary Route 66 road trip is arguably one of the most famous in the world, crossing eight states and three time zones. The trip will take you past some of the country’s most iconic roadside scenes, from neon signage and middle-of-nowhere truck stops to kitschy Americana.

The Ultimate Route 66 Road Trip: From Illinois to California

Photo| Route 66 map| GETTYIMAGES – DRMAKKOY

With around 4,000 kilometres of road to cover, planning a Route 66 road trip requires research and travel planning. With over 400 million annual visitors to HotelsCombined, we’ve done the hard work for you and highlighted the top Route 66 sights and pit stops in each state as well as the best places to stay.

High Angle View Of River Amidst Buildings In City

Photo| Chicago river with high rise building on a background| GETTYIMAGES – RAZVAN SERA – EYEEM

Chicago river skyline and Michigan avenue

Photo| Chicago river skyline and Michigan avenue| GETTYIMAGES – LIGHTKEY

Illinois

The symbolic start of a Route 66 road trip is the Buckingham Fountain in Chicago’s Millennium Park. Get orientated at the Route 66 Welcome Center at the Joliet Area Historical Museum, then head out to explore some of the best pit stops in Illinois. Most notably several historic gas stations in Dwight, Odell and Mt. Olive. Also, don’t miss the world’s largest catsup bottle in Collinsville and colourful outdoor murals in Pontiac.

Top Route 66 Sights in Illinois

  • Route 66 Eastern Terminus Sign, Chicago – A historic sign marking the start of the iconic highway.
  • Lauterbach Muffler Man, Springfield – A giant holding an American flag, this popular piece of kitschy Americana has remained mostly unchanged since 1962.
  • Illinois Route 66 Hall of Fame and Museum, Pontiac – A museum filled with Route 66 artefacts and historic memorabilia such as photos and license plates.
Retro Style Scene of old gas station in Arizona Desert

Photo| Retro Style Scene of old gas station| GETTYIMAGES – CHARLES HARKER

Where to Stay in Illinois

Chicago Athletic Association

Chicago Athletic Association Hotel, top hote for route 66 road trip

Photo| Chicago Athletic Association Hotel| Provided by ICE PORTAL

Start your road trip at the luxe Chicago Athletic Association, which is set in a prime location across from Millennium Park. It’s home to seven of the city’s best-loved dining establishments, from the seasonal menu at Cindy’s to American farm-to-table dishes in the Cherry Circle Room. Alternatively, let loose in the Game Room with cocktails and billiards, shuffleboard and bocce ball.

Elegant rooms and suites offer traces of their athletic heritage along with contemporary amenities, including complimentary Wi-Fi, gourmet mini bars and 24-hour in-room dining. Upgrade to one of the Holy Cow Suites for cosy fireplaces, separate seating areas and extra bedrooms.

Star Rating: 4*
Price: USD 234 – USD 658
Guest Rating: 8.9
Address: 12 South Michigan Avenue, Chicago, IL 60603, United States

Night Aerial View of Downtown Branson, Missouri and Lake Tanycomo

Photo| View of Downtown Branson, Missouri and Lake Tanycomo| GETTYIMAGES – JEREMYMASONMCGRAW.COM

Gateway Arch

Photo| Gateway Arch in Mississippi River in Saint Louis| GETTYIMAGES – DENISTANGNEYJR

Missouri

From St. Louis to Joplin, the Route 66 road trip takes you through many fascinating towns in Missouri, including quirky-named towns such as Bourbon, Cuba and Doolittle. The pedestrian and bike-friendly Chain of Rocks Bridge is a highlight in Springfield, famed for its 22-degree bend in the middle, while the Route 66 Car Museum with its classic cars is beloved with Route 66 fans.

Top Route 66 Sights in Missouri

  • 66 Drive-In Theater, Carthage – On warmer months, catch a flick at this historic drive-in theatre that dates back to 1949.
  • Giant Rocking Chair, Cuba – Built for the purpose of breaking the Guinness World Record for large rocking chairs, this nearly 13-metre-tall chair sits in front of Fanning Outpost General Store.
  • Wagon Wheel Motel, Cafe and Gas Station, Cuba – Dating back to 1936, this mom and pop food, fuel, and lodging establishment boasts a flickering neon sign that still welcomes visitors from all over the world.
Horses and riders crossing the river on a foggy autumn morning

Photo| Horses and riders crossing the river on a foggy morning in the Ozarks| GETTYIMAGES – BETH WATSON

Where to Stay in Missouri

Hyatt Regency St. Louis At The Arch

Hyatt Regency St. Louis At The Arch, top hotel for route 66 road trip

Photo|Hyatt Regency St. Louis at the Arch|Provided by ICE PORTAL

Take a break from your road trip and unwind at Hyatt Regency St. Louis At The Arch, which overlooks the iconic Gateway Arch. In addition to easy access to downtown’s top attractions, you can enjoy locally sourced farm-to-table cuisine at RED Kitchen or sizzling steaks at Ruth’s Chris Steak House. For craft beers and homemade BBQ, visit Brewhouse Historical Sports Bar.

Wake up to iconic Gateway Arch views from one of the stylish rooms, which feature oversized workstations and cosy lounge areas. Suites add extra living space, with the spacious Family Suite King ideal for those travelling with little ones. Go all out with a stay in the posh Executive Suite King, which offers sweeping downtown St. Louis views, a separate living room and 70 square metres of space.

Star Rating: 4*
Price: USD 93 – USD 193
Guest Rating: 8.8
Address: 315 Chestnut Street, St. Louis, MO 63102, United States

Country Club Plaza at the blue hour

Photo| Country Club Plaza| GETTYIMAGES – DEREK SLAGLE

Downtown Kansas City and Union Station

Photo| Downtown Kansas City and Union Station| GETTYIMAGES – DEREK SLAGLE

Kansas

Crossing the southeastern corner of Kansas, a Route 66 road trip in The Sunflower State is only 20 kilometres, the shortest segment of any state. There are only three towns on the route: Galena, Riverton and Baxter Springs, but there are still a few noteworthy landmarks. History enthusiasts will love the exhibits at Galena Mining and Historical Museum, while the Old Riverton Store has been a road trip staple since 1925 with its classic deli sandwiches.

Top Route 66 Sights in Kansas

  • Kan-O-Tex Service Station, Galena – This roadside filling station originally served Route 66 motorists in 1934, and also helped inspire the character “Tow Mater” in the movie Cars.
  • Old Riverton Store, Riverton – Visit the oldest continuously operated store on Route 66, which serves as a market, deli, general store, and Route 66 souvenir shop.
  • Rainbow Bridge, Baxter Springs – The only Marsh arch bridge left on Route 66.

Where to Stay in Kansas

The Old Riverton Post B&B

HotelsCombined visitors love the excellent value for money you get when staying at The Old Riverton Post B&B, which features bright and whimsical decor in the welcoming second-story inn. With only two rooms, you’re guaranteed personalized service, as well as a hearty continental breakfast with pastries, fruit, coffee and juice.

The pet-friendly rooms offer access to everything you need for a memorable stay, including a full kitchen, dining room, coffee nook and small sofa bed. The hosts recommend grabbing a cold beverage, propping your feet on the covered balcony and enjoying the front-row seat to small-town USA.

Star Rating: No Rating*
Price: USD 69 – USD 79
Guest Rating: 9.4
Address: 7378 SE 70th St, Riverton, KS 66770

Bricktown, Oklahoma City

Photo| Bricktown Canal in Oklahoma City| GETTYIMAGES – DENISTANGNEYJR

Buffalo

Photo| Buffalo| GETTYIMAGES – GARY KEMP PHOTOGRAPHY

Oklahoma

Boasting more kilometres of Route 66 than any other state, Oklahoma is the embodiment of America’s heartland. Before placing your bets on one of its classic casino hotels, make a pit stop at Clinton’s Oklahoma Route 66 Museum, which offers a look at the history of Route 66 and how it changed America. Don’t miss famous landmarks such as the world’s largest concrete totem pole in Chelsea, the giant blue whale in Catoosa and the photo-worthy Round Barn in Arcadia.

Top Route 66 Sights in Oklahoma

  • Pops 66 Soda Ranch, Arcadia – See the 20 meter-tall soda bottle made of LED lights and get a sugar rush with over 700 kinds of soda.
  • Will Rogers Memorial Museum, Claremore – Learn more about the life of Will Rogers, a famous performer and cowboy from Oklahoma.
  • Waylan’s Ku-Ku Burger, Miami – Drive through or sit down at this quirky eatery that looks like a cuckoo clock from the outside.

Where to Stay in Oklahoma

Hyatt Regency Tulsa

Hyatt Regency Tulsa, top hotel for route 66 road trip

Photo| Hyatt Regency Tulsa| Provided by ICE PORTAL

Located in the heart of the vibrant entertainment district, Hyatt Regency Tulsa is a top luxury hotel in downtown Tulsa. Overlooking the scenic gardens of the Williams Center Complex, the hotel offers sit down dinners at Daily Grill. Alternatively, opt for a coffee to-go at Topeca Coffee or sip wine and beer at Daily Grill Lounge.

Feel at home in the spacious rooms, all of which boast comfortable Hyatt Grand beds, work desks, HDTVs, coffee makers and mini fridges. If you need some extra space from your travelling companion, stay in one of the Luxury Suites with a separate living room.

Star Rating: 4*
Price: USD 91 – USD 119
Guest Rating: 8.4
Address: 100 East 2nd Street, Tulsa, OK 74103, United States

Capitol building, aerial skyline, sunset, Austin, TX, Texas State Capital

Photo| Capitol building in Austin| GETTYIMAGES – DSZC

Skyline - Dallas, Texas

Photo| Dallas business district| GETTYIMAGES – SPORTSTOCK

Texas

A classic Route 66 road trip through Texas goes through the Panhandle on Interstate 40, which starts with the giant neon state of Texas sign in McLean. Take the time to browse the Route 66 artefact-filled Devil’s Rope Museum in McLean. Alternatively, visit the must-see Cadillac Ranch in Amarillo to see half-buried classic Cadillacs that form an iconic piece of artwork, which was built by artists from San Francisco in 1974.

Top Route 66 Sights in Texas

  • Conoco Tower Station, Shamrock – Dating back to 1936, this Art Deco attraction operates as a museum and is particularly photogenic at night when lit up.
  • Midpoint Cafe, Adrian – Serving as the mid-point between Los Angeles and Chicago, this 50s-style pit stop serves classic diner favourites.
  • Sixth Street Historic District, Amarillo – The 13 blocks include art galleries, antique and collectable stores, restaurants, and bars in historic buildings.
oil pumpjacks

Photo| Oil pumpjacks at sunset| GETTYIMAGES – SHARPLY_DONE

Where to Stay in Texas

Courtyard by Marriott Amarillo Downtown

Courtyard by Marriott Amarillo Downtown, top hotel for route 66 road trip

Photo| Courtyard by Marriott Amarillo Downtown| Provided by BOOKING.COM

Courtyard by Marriott Amarillo Downtown is the perfect spot to unwind after a long day of driving. Catch up on the latest shows on your flat-screen TV, do some travel planning with the free Wi-Fi or sink into the plush pillow top mattress after a long day. Large windows offer spectacular views of downtown, while upgraded Suites add sitting areas and sofa beds.

The on-site restaurant The Bistro serves breakfast favourites and a variety of dinner choices, as well as beer and wine in the evening. Don’t forget a Starbucks coffee for a caffeine boost to start your day. Additionally, there’s a 24-hour market available with a tasty selection of on-the-go snacks and beverages.

Star Rating: 3*
Price: USD 95 – USD 206
Guest Rating: 8.7
Address: 724 South Polk Street, Amarillo, TX 79101, United States

A majestic hot air balloon soars under the stars of the Milky Way, over the desert - Mesquite Dunes of Death Valley National Park. Moonlight provides luminosity showing the patterns and shapes of the desert landscape.

Photo| Hot air balloon over Mesquite Dunes of Death Valley National Park| GETTYIMAGES – MATT ANDERSON PHOTOGRAPHY

hiking at Kasha-Katuwe Tent Rocks National Monument in New Mexico. USA.

Photo| Hiker at Kasha-Katuwe Tent Rocks National Monument| GETTYIMAGES – FERRANTRAITE

New Mexico

If you started your Route 66 road trip in Chicago, once you drive into New Mexico you’re more than halfway to the end and officially in the American Southwest. Start snapping photos of the vintage neon signs and retro motels in Tucumcari, then keep your eyes peeled for the murals paying tribute to the town’s storied history as a famous pit stop destination. To see classic cars and vintage gas pumps, add the Route 66 Auto Museum in Santa Rosa to your itinerary.

Top Route 66 Sights in New Mexico

  • San Miguel Mission, Santa Fe – Built in 1625, it is the oldest church in the United States.
  • San Jose Mission Church, Laguna – A traditional pueblo building made of adobe that was built in 1701 and serves as a religious centre.
  • Blue Swallow Motel, Tucumcari – Built just before the beginning of World War II, this iconic vintage 1940s motel has a postcard-perfect neon sign.
Late afternoon in the Red Rocks area of Northern New Mexico featuring amazing colors and rock formations

Photo| Red Rocks area of Northern New Mexico| GETTYIMAGES – DEAN FIKAR

Where to Stay in New Mexico

Hotel Albuquerque At Old Town – Heritage Hotels and Resorts

Hotel Albuquerque At Old Town - Heritage Hotels and Resorts, top hotel for route 66 road trip

Photo| Hotel Albuquerque at Old Town – Heritage Hotels and Resorts| Provided by BOOKING.COM

Hotel Albuquerque At Old Town – Heritage Hotels and Resorts is conveniently placed in the heart of the Old Town, offering luxe perks such as multiple restaurants and bars and an outdoor swimming pool. Nightlife is highlighted by the hotel’s intimate flamenco theatre and lively QBar Lounge.

Traditional Guest Rooms boast Keurig brewers, refrigerators and expansive views of the Albuquerque Sandia Mountains, while some Junior Suites add private balconies with downtown Albuquerque and Old Town views and separate sitting areas. Looking for romance? The opulent Presidential Suite has over 110 square metres of living space.

Star Rating: 3*
Price: USD 135 – USD 204
Guest Rating: 8.7
Address: 800 Rio Grande Blvd Nw, Albuquerque, New Mexico, United States

Antelope Canyon, Arizona, USA

Photo| Lower Antelope Canyon| GETTYIMAGES – SPONDYLOLITHESIS

Horseshoe Bend At Sunset

Photo| Horseshoe Bend| GETTYIMAGES – ANSONMIAO

Arizona

Arizona is full of classic Route 66 road trip attractions, including retro motels and gas stations, as well as iconic American destinations such as the Grand Canyon. Enjoy retro-chic photo-ops in Williams, including the bright red car on the roof of Cruiser’s Route 66 Cafe, then browse the vintage cafes and stores in the photogenic Seligman. The Arizona Route 66 Museum in Kingman is an essential Route 66 stop, as well as the burro-filled streets of Oatman.

Top Route 66 Sights in Arizona

  • Hackberry General Store, Hackberry – A short drive up from Kingman, this unique store is full of Route 66 memorabilia and kitschy souvenirs.
  • Meteor Crater Natural Landmark – Visit the site where a meteor crashed into the ground around 50,000 years ago.
  • Petrified Forest National Park, Holbrook – Marvel at the unique stone formations, petrified trees and natural multi-coloured badlands.
Meteor Crater, Arizona

Photo| Meteor Crater, Arizona| GETTYIMAGES – CHARLES DAVIES

Where to Stay in Arizona

Little America Hotel Flagstaff

Little America Hotel Flagstaff, top hotel for route 66 road trip

Photo| Little America Hotel Flagstaff| Provided by ICE PORTAL

A perfect home base if you want to explore the Grand Canyon, Little America Hotel Flagstaff has a host of amenities and services for weary travellers. In addition to a Travel Center with a 24-hour convenience store, it highlights quintessential Arizona flavours in its highly-rated Silver Pine Restaurant & Bar. It’s inviting outdoor pool is a welcome respite after a day of travelling in the car.

Sitting among some of America’s most beautiful natural scenery, stylish rooms feature sitting areas, flat-screen TVs, Keurig coffee makers and high-speed Wi-Fi. Families and groups can upgrade to a Two Queen with Sofa, while Apartment Suites boast a full kitchen and spacious living room. Upgraded suites add romantic marble fireplaces.

Star Rating: 3.5*
Price: USD 129 – USD 699
Guest Rating: 9
Address: 2515 East Butler Avenue, Flagstaff, Arizona, United States

Young Woman Walking Down Palm Trees Street Revealing Downtown Los Angeles

Photo| Woman walking down a street toward Downtown Los Angeles| GETTYIMAGES – DUTCHERAERIALS

DTLA Downtown Los Angeles

Photo| Downtown Los Angeles| GETTYIMAGES – LPETTET

California

California is the last stretch on a Route 66 road trip, home to big-city Los Angeles and the sandy beaches lining the Pacific Ocean. A sign at the end of the Santa Monica Pier marks the end of the legendary highway, but before that, you can explore quirky California landmarks. See a McDonald’s made from old railroad cars or browse artefacts in Route 66 Mother Road Museum in Barstow, then admire tree-shaped glass sculptures in Elmer’s Bottle Tree Ranch in Helendale.

Top Route 66 Sights in California

  • Broadway Theater and Commercial District, Los Angeles – Admire the building facades in this historic theatre district — the largest of its kind in the United States.
  • Wigwam Motel, San Bernardino – This kitschy lodging and historic landmark dating from 1949 features towering tepees.
  • Mojave National Reserve, Kelso – A 64,000-hectare desert park ideal for hiking and spotting local wildlife.
Dusk at Santa Monica Pier

Photo| Santa Monica Pier at sunset| GETTYIMAGES – EXTREME-PHOTOGRAPHER

Where to Stay in California

Loews Santa Monica Beach Hotel

Loews Santa Monica Beach Hotel, top hotel for route 66 road trip

Photo| Loews Santa Monica Beach Hotel| Provided by BOOKING.COM

One of Santa Monica’s luxury beachfront hotels, Loews Santa Monica Beach Hotel is an ideal place to wrap up your Route 66 road trip. In addition to an ocean-view pool and pampering Ocean Spa, you can enjoy locally-caught seafood paired with ocean views at Ocean & Vine Restaurant. Alternatively, opt for campfire-inspired oceanfront fire pits at Blue Streak or rent a bike and cruise the area on two wheels.

The rooms at Loews Santa Monica Beach Hotel feature contemporary furnishings and ocean views, including the enticing Oceanfront Fire Pit Suite with a furnished patio and fire pit. The custom-designed suites are even more luxurious, from the Poolside Cabana Room and Boho Terrace Luxury Suite to the Santa Monica Luxury Suite.

Star Rating: 4*
Price: USD 425 – USD 4,000
Guest Rating: 8.3
Address: 1700 Ocean Avenue, Santa Monica, CA 90401, United States

Hotel Location

Explore the Heart of America on a Classic Route 66 Road Trip

public street neon route 66 sign at night in Albuquerque

Photo| Neon route 66 sign at night in Albuquerque| GETTYIMAGES – DSZC

Whether you’re with the family, on a couple’s trip or travelling solo, there’s no better way to see some of America’s greatest landscapes than on a Route 66 road trip. Offering a trip-of-a-lifetime, Route 66 boasts iconic U.S. landmarks, national parks and historic sites along the much-loved byway. Pack your bags and enjoy the view!

What is your favourite Route 66 road trip destination? Let us know in the comments below.

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