Visit Chicago, Springfield, St Louis, Oklahoma City, Amarillo, Albuquerque, Winslow, Grand Canyon NP, Las Vegas & Los Angeles.
This Route 66 road trip is an all-time classic that has been etched into American folklore by those migrating west along “The Mother Road” during the Great Depression of the 1930s. Route 66 offers over 2,400 miles of nostalgic Americana, ever-changing scenery and some of America’s best cities. Starting your road trip in Chicago, you’ll cross through eight States as you drive to Route 66’s “End of the Trail” sign in sunny Santa Monica, Los Angeles.
Route 66 road trip highlights:
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We’ll suggest properties to match your preferred budget, be it low-cost, mid-range or high-end luxury that you’re looking for. We can also mix it up so you’ll experience a range of standards and experiences along your Route 66 road trip.
All of our road trips can be tailored to meet your requirements. Do you have more or less than 15 days for your Route 66 road trip? No problem, we can bolt on extra nights to allow more time to explore or shorten the number of destinations as required.
You’ll begin your Route 66 road trip by spending three nights and two exciting days in Chicago. Many start by enjoying Chicago’s famous pizza or by going to the top of Willis Tower to watch the sunset and get the lay of the land. You’ll collect your wheels when you leave Chicago to begin the drive down Route 66. For now, you’ll be pounding the pavement from one outstanding attraction to another.
Most visitors to Chicago head straight to the ‘Magnificent Mile’, a vibrant, bustling area which is home to upscale shops, trendy restaurants and posh hotels. Landmarks include the historic Chicago Water Tower, the neo-Gothic Tribune Tower and the 100-story Hancock Center, which has a rooftop observation deck called 360 Chicago. Spend the rest of the day exploring some of the other attractions found north of the Chicago River. These include Navy Pier, Wrigley Field and the beaches along Lake Michigan’s shoreline.
On your final full day in Chicago, we recommend that you enjoy the city’s attractions that are found south of the Chicago River. Some of America’s very best museums are located in Chicago, including the Art Institute, the Alder Planetarium, and the Field Museum of Natural History to name just three. Be sure to stroll around Millennium Park; you’ll find world-famous outdoor artworks like Cloud Gate and Crown Fountain for those all-important Social Media snaps. Lastly, before leaving for Route 66, make sure you spend at least one evening partying at Buddy Guy’s Legends Nightclub.
Start your engines; iconic Route 66 awaits. After collecting your Route 66 wheels, we recommend you head to Jackson Blvd, where you can pass the small Route 66 sign that marks the beginning of your Mother Road adventure. Driving Route 66 through Illinois is super easy, as it’s really well-signposted and surprisingly rural once you’ve left the city of Chicago. Along the way to Springfield, you’ll enjoy highlights such as Route 66 obsessed Pontiac and the historic Standard Oil Gas Station in Odell. Once you arrive in Springfield, history enthusiasts will want to visit Abraham Lincoln’s Tomb, the Lincoln Presidential Museum and the Lincoln Home.
Onto St. Louis today, which sits on the banks of the Mississippi River. Highlights include the Missouri Botanical Gardens, Citygarden and the famous Gateway Arch National Park. If you have time, try to catch a baseball game at the Cardinals stadium, which is located right in the heart of the city. Remember that you’ll be provided with a detailed Road Trip Pack, which will guide you through all the Route 66 roadside attractions and much more.
Today, you’ll continue to drive southwest on Route 66, and pass through the State of Missouri. En route, we recommend you visit Meramec Caverns, which are located in the Ozarks region. These vast caverns are an extensive set of limestone caves offering remarkable subterranean tours. You’ll finish the day in Springfield, Missouri, which is officially recognised as the birthplace of Route 66.
Get an early start and continue along the Mother Road to Tulsa. You’ll pass through Joplin before skimming through a corner of Kansas and into Oklahoma. In Tulsa, we recommend visiting the Philbrook Museum, home to a vast art collection housed in an Italian-style villa surrounded by idyllic gardens. During the afternoon, you’ll continue along Route 66 to Oklahoma City. Visit the Bricktown District for an evening meal at one of the numerous diners and restaurants. Lastly, before turning in for the evening, consider visiting the Oklahoma City National Memorial, which remembers the victims and survivors of the 1995 Oklahoma City bombing. This perfectly executed dedication is especially moving at night.
Spend the morning at the incredible National Cowboy and Western Museum before checking out the real-life cowboys over in Stockyard City. If you still have the energy, then the daring amongst you should check out some of the activities at Riversport Adventure Park. Your amazing Route 66 Road Trip Pack will show you the way to Amarillo. You’ll pass some fantastic Route 66 museums along the way, filled with nostalgic Americana, classic cars and much more. Once you hit Amarillo, there’s only one place for any true road-tripper to go for dinner. The Big Texan Steak Ranch & Brewery (pictured) is a must, just make sure you arrive hungry, as the portions are huge.
Today’s drive are packed with classic Route 66 attractions like Cadillac Ranch (pictured), The Midpoint Cafe and the Route 66 Auto Museum in Santa Rosa. You can then opt to finish the day with an overnight stop in either Albuquerque or Santa Fe. We’ll talk you through the benefits of both options when you request a quote from us. Santa Fe lies on the old or original Route 66 route, offering an upmarket spa town feel. Albuquerque lies on the newer, more direct route and is famous for the Sandia Peak Tramway and “Breaking Bad” filming locations.
El Morro is a detour away from Route 66 that’s worth considering, see ‘inscription rock’, a large sandstone pueblo where travellers since the 17th century have left messages to mark their visit. Later in the day, you’ll pass through two Natural Wonders – Painted Desert (pictured) and Petrified Forest National Park, before returning to Route 66 and heading west to the classic Route 66 overnight stop of Winslow, Arizona.
The awe-inspiring Grand Canyon is located one hour’s drive north of Route 66. The world’s largest and most famous geological wonder is simply staggering. Two billion years in the making, the Colorado River has forged a mile deep, 18 mile wide and 277 mile long slice into the Arizona landscape that will stay with you forever. Before leaving Route 66, however, you’ll get the chance to experience another natural wonder, the Meteor Crater. It is not as large a void as the Grand Canyon, but in many ways, it is just as spectacular and intriguing.
Again, it’s not strictly on Route 66, but Las Vegas is so close that it would be rude not to pop by and say hello. Along the way, you’ll pass by many iconic Route 66 places like the town of Seligman and Hackberry General Store. As you get closer to Vegas, you’ll pass the Hoover Dam before seeing the bright lights of Las Vegas in the distance.
If your head hurts after a big night out, why not chill out by one of the stunning swimming pools that adorn every hotel. Alternatively, you can explore the legendary ‘Strip’ and get tickets to see an extraordinary show. Witness the Bellagio Fountains in full flow, or take a Gondola ride at the Venetian. A visit to The Neon Museum will appeal to many. Here, you can encounter the magic of Las Vegas from a bygone age, by touring the Neon Boneyard. Driving enthusiasts might want to test their skills at Speed Vegas, where you can drive supercars around a thrilling race track. Just let us know if you want more time to enjoy Las Vegas before returning to Route 66.
The iconic Santa Monica Pier signals the final stop of your Route 66 road trip. To celebrate the finale of your journey, we suggest you enjoy a rewarding meal at one of the Pier’s many eateries that overlook the Pacific Ocean and take a picture by “The End of Trail” sign. After lunch, we suggest you take a stroll and explore Santa Monica and neighbouring Venice Beach.
Spend the day relaxing by the pool after your Route 66 adventure, or head out to explore the sites of Los Angeles. There’s plenty to keep you busy. Hollywood is synonymous with glitz and glamour, and it’s the most visited part of the city. The Griffith Observatory is just a short drive northeast of here, perched high on a hill overlooking the urban sprawl. This famous landmark is well worth visiting and offers excellent views of the legendary Hollywood Sign. We could go on, so if you want more time in LA, then just let us know.
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You’ll find answers to most of your Route 66 questions right here. If you still need assistance, then feel free to get in touch, and we’ll be sure to get back to you.
Traditionally, Route 66 is best experienced by starting in Chicago and ending at the “end of the trail” sign in Santa Monica, Los Angeles, heading west like all those Americans from yesteryear searching for a better life out west. Starting in Los Angeles and finishing in Chicago has its upsides too; our friendly and knowledgeable team will help you consider the best direction of travel for you and your party.
The best months to drive Route 66 are between May and October. With May, June and September being the three optimal months, as these offer the best value for money and climate.
Our Route 66 road trips start at just £1,599 per person, with more luxury versions costing up to £3,999 per person. We’ll produce a personalised quote to match your requirements and preferred dates.
You’ll need to spend between 15 and 21 nights to drive Route 66 comfortably. Whilst many people squeeze Route 66 into 14 nights, it’s best to allow a little more time so you can fully explore each stop along The Mother Road.
Please use the form below to request a quote from our team. Fields marked with an * are mandatory. Please note that we currently only serve customers based in the UK & The EU.
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