Visit Chicago, Springfield IL, St. Louis, Springfield MO, Tulsa, Oklahoma City, Amarillo, Santa Fe, Winslow, Meteor Crater, Barstow & LA.
This most historic version of all our Route 66 road trips is one for the purists. It stays true to the original or old Route 66 route for the entire drive from Chicago to Santa Monica in California. This old-school road trip along the “Mother Road” will not disappoint those looking for an authentic American road trip.
Key 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 road trip.
All of our American road trips can be tailored to meet your requirements. Do you have more or less than 14 days for your 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 start 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 spend time visiting the city’s attractions that are located south of the Chicago River. Some of America’s very best museums are found here, including the Art Institute, the Alder Planetarium, and the Field Museum of Natural History. 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 town, make sure you spend at least one evening partying at Buddy Guy’s Legends Nightclub.
After collecting your road trip 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 here 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 southwest through the State of Missouri. En route, we recommend you stop by Meramec Caverns, which are located in the Ozarks region. These vast caverns are an extensive set of limestone caves offering unforgettable underground tours. You’ll finish the day in Springfield, Missouri, which is officially recognised as the birthplace of Route 66.
Continue west along the Mother Road, you’ll pass through Joplin before skimming through a corner of Kansas and into Oklahoma. Once you’re in the city of Tulsa, we highly recommend visiting the Philbrook Museum, home to a vast art collection housed in an Italian-style villa surrounded by extensive idyllic gardens.
En route, we recommend that you fill up with gas and refreshing soda at Pops, an iconic stop on Route 66 located in the town of Acadia. Once you’ve arrived in Oklahoma City, we recommend a visit to the Bricktown District of the city for a bite to eat at one of the numerous diners and restaurants found here. Lastly, before leaving town, consider visiting the moving Oklahoma City National Memorial, which remembers the victims and survivors of the 1995 Oklahoma City bombing.
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 Riversport Adventure Park. Your Road Trip Pack will show you the way to Amarillo; it’s found due west in the heart of the Texas Panhandle. You’ll pass some fantastic Route 66 museums along the way, packed with nostalgic Americana, classic cars and 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 is a must, just make sure you arrive hungry, as the portions are HUGE.
On the way from Amarillo to Santa Fe, you’ll get the chance to visit some classic Route 66 holiday attractions. These include Cadillac Ranch (pictured), Midpoint Cafe and the Route 66 Auto Museum in Santa Rosa. You’ll finish the day off in Santa Fe, New Mexico, which lies along the path of the original Route 66 route. Santa Fe is home to gorgeous adobe-style buildings, beautiful resorts and swanky spas.
Included in your Road Trip Pack are plenty of detailed suggestions about what to do and see en route. One highlight of the day is The Painted Desert, which offers up multicoloured rock formations to amaze. You’ll then cruise through Petrified Forest National Park on your way to a firm favourite of ours, Meteor Crater (pictured), near Winslow in Arizona. After a busy day, you’ll rest up overnight in Flagstaff, a classic Route 66 stopover town.
The iconic small towns of Route 66 keep on coming today; you’ll pass through Seligman, Hackberry, Oatman and Amboy on your way west to Barstow. Be sure to have your phone or camera ready to capture classic Mother Road snaps as you go. Today is the last lengthy drive of the holiday, and please remember that the mileage is nothing to be overly concerned about; you’ll soon eat up the miles as you cruise along the open roads of Route 66, listening to your road trip soundtrack as you go.
The iconic Santa Monica Pier signals the final stop of your Route 66 holiday. 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 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 questions right here. If you still need assistance, Feel free to get in touch, and we’ll be sure to get back to you promptly!
Not a problem. If you are lucky enough to have extra time to explore more places or add more rest days, then just let us know and we’ll adjust your trip to match your preferred timescale.
We strongly advise that you purchase travel insurance for your holiday to cover you against medical expenses, theft and other financial costs. Should you need to cancel before travelling, some insurance policies may pay out for any loss of funds that have been paid to us and which cannot be refunded under our cancellation policy.
Many of our trips have a different end destination than the starting point, so this is not a problem. Please note a fee sometimes applies for one-way rentals between other regions or states, which will be paid to the supplier directly when collecting the vehicle. We’ll endeavour to inform you of this charge within your quote.
No, far from it. We work with a range of properties from 3* to 5*, so we can adapt the trip to match most budgets. We have access to rooms in more than 800 hotels, motels, lodges and B&Bs across North America.
The minimum age to rent a car is 21 in the United States or Canada, although, in addition, any drivers under 25 years of age will generally incur a surcharge.
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Not quite what you’re looking for? Get in touch to discuss your Bespoke Road Trip plans, or check out these similar road trip itineraries…
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