Visit Chicago, Springfield, St. Louis, Tulsa, Oklahoma City, Santa Fe, Monument Valley, Antelope Canyon, Horseshoe Bend, Grand Canyon NP, Las Vegas, Joshua Tree NP, Palm Springs & Los Angeles.
Looking for the ultimate Route 66 itinerary from Chicago to Los Angeles? Want a road trip with a slower pace that explores a little further off the beaten track? Then this three-week Mother Road itinerary is the one for you.
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 road trips can be tailored to meet your exact requirements. Do you have more or less than 21 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.
Start your engines; iconic Route 66 awaits. 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.
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. 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 delicious soda at “Pops.” this is an iconic Route 66 stop-off in the town of Acadia. Once you’ve arrived in Oklahoma, we recommend you visit the Bricktown District of the city for a bite to eat at one of the numerous diners and restaurants found here. 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. As always, remember that your detailed Road Trip Pack will inform you of all the visitor attractions in the city and the surrounding area.
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 simply 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.
A full day at leisure in the chilled-out atmosphere of Santa Fe. Spend the day by the pool or shopping in local boutiques. Art lovers might want to hunt out some culture at one of the city’s galleries. A favourite of the team is the amazing Georgia O’Keeffe Museum.
Put your spurs and chaps on and head west to cowboy country. Witness the proud and majestic “Mittens”, which appear to be made up of every shade of orange and red possible. This is another chance to prove your photography skills, although the scenery is so stunning here that even a novice will look like a pro.
The world’s largest and most well-known geological wonder is just staggering, welcome to Grand Canyon National Park. Two billion years in the making, the Colorado River has forged a mile-deep, 18-miles wide and 277-mile long gauge into Arizona. En route, you can opt to detour to Page, where you’ll find further natural wonders like Antelope Canyon and Horseshoe Bend. It’s well worth an early start.
After watching the sunrise over the Grand Canyon, you’ll leave this bucket-list National Park, head south to Williams, and then west along Old Route 66. You’ll pass through iconic Route 66 towns like Seligman and Hackberry before passing the Hoover Dam and entering the most legendary party town on the planet – Las Vegas.
If your head hurts after a big night out, then why not chill out by one of the fantastic swimming pools that adorn every hotel. Alternatively, you can explore the legendary ‘Strip’ and book tickets to see an outstanding show or shop until you drop at one of the city’s excellent malls.
Las Vegas has something for everyone; why not take a helicopter ride over The Grand Canyon or enjoy more of Las Vegas itself. Witness the Bellagio Fountains in full flow, or take a Gondola ride at the Venetian. A visit to The Neon Museum might appeal, where you can experience the Las Vegas magic of a bygone age by touring the Neon Boneyard. Whilst, driving enthusiasts might want to test their skills at Speed Vegas, where you can drive exotic supercars around a thrilling race track.
Start the day by driving through the stunning and serene Mojave Desert. Continue south, and you’ll enter the unique and crazy world of Joshua Tree National Park, which looks like something straight out of a Dr. Suess book. Between these two incredible desert experiences is the classic Route 66 town of Amboy. Be sure to stop by the iconic Roy’s Motel and Cafe along the way. Once you’ve arrived in Palm Springs, you can relax by the pool or explore the city’s neighbourhoods for the classic 50s architecture homes that adorn the city’s streets.
The Santa Monica Pier signals the final stop of your Route 66 holiday. To celebrate the conclusion of your journey, we suggest you enjoy a rewarding meal at one of the Pier’s many eateries that overlook the Pacific Ocean.
Hollywood is synonymous with glitz and glamour, and although many studios have moved to other parts of Los Angeles, it’s still fun to visit the home of the Oscars and walk along Hollywood Boulevard looking for the handprints of your favourite movie stars. Just a short drive northeast of here lies the Griffith Observatory, perched high on a hill overlooking the urban sprawl of LA; this landmark is well worth a visit, and it also offers excellent views of the legendary Hollywood sign.
Enjoy your final full day in lively Los Angeles. Why not spend some time discovering millionaire and celebrity homes in Beverly Hills. Or, you’d prefer to enjoy the world-class architecture and artwork at the unique Getty Center in Bel-Air. Tonight, have dinner in downtown Los Angeles as you take in the skyscraper scenery. Tomorrow, you’ll fly home from LAX after spending the morning finishing off any final sightseeing or shopping.
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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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