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My 2-Week Route 66 Itinerary – Wild Junket Adventure Travel Blog

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My 2-Week Route 66 Itinerary – Wild Junket Adventure Travel Blog

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Last Updated on March 23, 2023 by Nellie Huang

Are you planning a Route 66 road trip? Illinois local, Chad Emery, has designed a detailed Route 66 itinerary for those dreaming of the ultimate USA road trip! 

Imagine cruising down a historic highway, the wind in your hair, and the open road stretching out before you.

Welcome to Route 66, one of the most iconic road trips in the world! This legendary highway spans over 2,400 miles from Chicago to Santa Monica, offering a journey through America’s heartland and the Southwest. As you make your way along the road, you’ll discover a treasure trove of Americana: from neon-lit motels and roadside diners to quirky attractions and stunning natural wonders. .

I was born and raised in Towanda, Illinois – right along Route 66 – and have years of experience traversing this epic route. In this Route 66 guide, I’ve included all that I know about driving Route 66, from how to navigate certain roads and what the best itinerary is. Grab your keys, rev up your engine, and join us on an unforgettable journey down the Mother Road!

route 66 road trip planner - route 66 itinerary

Route 66 Itinerary & Guide

The original Route 66 was established in the 1920s and stretched from Chicago to Los Angeles. Since then, some sections have changed and others have gone through construction. It’s still the same route in general though.

Today, Route 66 is a combination of smaller roads and big interstates. It takes you through everything from old ghost towns to nature reserves and big cities. There are a lot of sites to see along the way, so it’s definitely worth planning your Route 66 trip in advance!

My 2-Week Route 66 Itinerary – Wild Junket Adventure Travel Blog

Route 66 Itinerary Map

The first step of planning your Route 66 trip is figuring out how to get there. Route 66 starts in Chicago, Illinois and ends in Santa Monica, California.

Keep in mind that this itinerary is designed to help those of you who want to drive the entirety of Route 66 in two weeks. You’ll be driving at a comfortable pace: around 2-4 hours each day, with scheduled sightseeing breaks every other day. If you have time, I recommend taking 3 weeks to do this Route 66 road trip and spending more time at each spot.

I will be sharing a detailed day-to-day breakdown of what to do at each spot, with hotel and restaurant recommendations. Below is a general overview of my Route 66 itinerary on a map.

You can download this route itinerary on Google Maps. 

 How to Get to Route 66

By Air

Chicago is a major city in the US, so it’s pretty easy to get there using different methods of transportation. The major airports are O’Hare International Airport (ORD) and Midway International Airport (MDW). Most international airlines fly to one of these airports from Europe, Asia and other parts of the US. Flights from London to Chicago (8 hours) cost around $700 round trip. You can fly from Los Angeles to Chicago (4 hours) for around $300 return. If you’re coming from New York City (3 hours), it’ll cost around $250 round trip.

By Train

Another way to come to Chicago is by train. Union Station is located in downtown Chicago and is actually pretty close to the Route 66 starting point. You can get to Chicago from St. Louis (6 hours) for around $50 round trip. There’s also a route from New York City to Chicago (24 hours) that costs around $300 return. If you’re coming from the south, you can take the Amtrak Texas Eagle from San Antonio to Chicago (32 hours) for $400 return. Book your train tickets here.

route 66 by car - planning a trip on route 66

How Long to Drive Route 66?

Route 66 is just under 2,500 miles (4,000 kilometers) long, so it’s important to allow enough time to drive the whole way. In my opinion, two weeks is the perfect amount of time. You’ll get to make many stops and enjoy the sights along the way, without making  the trip feel too long. I wouldn’t recommend driving Route 66 in less than two weeks because you won’t have much time to stop.

If you have 3 weeks on route 66, you can easily use my itinerary and just add more days at each stop. In fact, those with lots of time can combine this Route 66 itinerary with a California road trip. Check out our recommended California itinerary.

route 66 itinerary map

How to Drive Route 66 

Car Rental

The best way to explore Route 66 is of course on four wheels.We recommend hiring a car or driving your own vehicle. For this Route 66 itinerary, you’ll need to rent the car in Chicago and return it in Los Angeles. Most car rental companies allow for different pick-up and drop-off spots, but there will be an extra charge.

Car rental in Chicago is not cheap, but you will at least get a quality car without any issues. On average, a 14-day car rental from Chicago to Los Angeles costs upwards of US$1000. This includes third-party liability and unlimited mileage. We always book with Discover Cars, as they’ve consistently given us the best prices and customer support. 

Book Your Car Rental!

route 66 road trip itinerary - 2 weeks on route 66

RV Rental

Renting an RV or campervan can be a great way to save money on accommodation and see the backcountry in a different perspective. We’ve driven RVs in Australia, Iceland, California, Spain, Switzerland, and France and we even used to own one ourselves. We love traveling in a campervan!

The best place to rent an RV is RVshare, the biggest RV community helping owners and renters get connected. Basically, you’ll be renting someone’s RV and the fee goes straight to the owner, which means prices are lower.

Motorcycle Rental

Always dreamt of riding a Harley Davidson along Route 66? Eagle Rider and Ride Free are two companies that allow one-way motorcycle rentals. Both also run guided motorcycle tours on Route 66. You’ll want to be conscious of the weather if you travel Route 66 by motorcycle though. The best time to travel on a motorcycle is in September or October.

route 66 by motorbike

2-Week Route 66 Itinerary

Day 1: Arrive in Chicago

Regardless of what time you land in Chicago, give yourself some time to relax on your first day. Both Midway and O’Hare airports are pretty big, so getting through them can take some time. Both have direct connections to downtown on the subway though (the trip takes about an hour). If you’re coming to Chicago by train, you’ll arrive right in downtown Chicago.

Where to Stay in Chicago

You have unlimited options when it comes to hotels in Chicago. Here are my recommendations for each budget:

Where to Eat in Chicago

Route 66 Itinerary Day 2: Sightseeing in Chicago

Start your day bright and early at the iconic Willis Tower Skydeck. You can take an elevator to the 103rd floor and see all of Chicago, plus the neighboring states on a clear day. You can even walk on the Ledge, a glass-floor feature that juts out of the building high above the ground. This is definitely best to do first thing in the morning — it gets busy by 11am. Book your tickets in advance.  

In the afternoon, hop on an architecture cruise along the Chicago River. You’ll get to see the whole city from the water, and the guides are usually pretty funny too. It picks up and drops off in Navy Pier, a busy promenade that juts out into Lake Michigan.

Then head to the Bean, also known as the Cloud Gate, one of Chicago’s most popular sights. The monumental work of art anchors downtown Millennium Park and reflects the city’s famous skyline and the surrounding green space. Continue on to Michigan Avenue, which runs north to south straight through downtown Chicago. It’s flanked by endless shops, restaurants, and tourist attractions. If you’re here around a meal time, I’d definitely check out Portillo’s for a true Chicago meal.

chicago - route 66 starting point

Day 3: Chicago to Springfield, Illinois

The drive from Chicago to Springfield takes about 3.5 hours. It’s best to drive outside of rush hour, since the interstate (I-55) you take leaves directly from downtown Chicago. There isn’t usually much traffic once you get out of Chicago. There isn’t any attraction along the way worth stopping at, so I recommend driving there directly.

I suggest staying in downtown Springfield near the Capitol Building because that’s where most of the attractions are.  For starters, you won’t want to miss the Abraham Lincoln Museum, a world-class institution that offers an in-depth look at the life and times of one of America’s greatest leaders. The Illinois State Capitol is another must-visit, with its awe-inspiring architecture and captivating exhibits.

For some nature, be sure to stop by the Washington Park Botanical Garden, where you can immerse yourself in the beauty of over 20 themed gardens and a stunning conservatory. And if you’re looking for some history, don’t miss the Dana-Thomas House and the Old State Capitol, both of which offer a glimpse into the rich heritage of this fascinating city.

springfield illinois - route 66 itinerary 14 days

Where to Stay in Springfield, IL

Where to Eat in Springfield, IL

You’ll find a lot of chain restaurants in the cities along Route 66, but I always recommend supporting local establishments.

Day 4: Springfield to Saint Louis, Missouri

After learning about Illinois’ history, it’s time to head to the next state on Route 66 — Missouri. Right across the state border is the charming city of Saint Louis. It only takes about an hour to drive from Springfield to Saint Louis, but make sure you follow the signs once you enter Saint Louis. The interstates all intertwine as soon as you cross the Mississippi River. 

One of my favorite sights in Saint Louis is the Gateway Arch,  Standing 630 feet above the Mississippi River is St. Louis’s most iconic landmark: the Gateway Arch. Architecturally and historically, the Arch is an engineering triumph and also serves to commemorate Thomas Jefferson, the Louisiana Purchase and pioneers settling the United States. You can take an elevator to the top to look over the Mississippi River and the entire city.

route 66 itinerary 2 weeks - saint louis

Where to Stay in St. Louis

I definitely recommend staying close to downtown Saint Louis. 

Where to Eat in St. Louis

Route 66 Itinerary Day 5: Sightseeing in St. Louis

The next morning, stop by the City Museum for a unique and interactive experience, with a giant outdoor jungle gym, slides, and a 10-story slide to explore. Then wander around the Missouri Botanical Garden, which boasts over 79 acres of beautifully landscaped gardens, as well as a vast collection of plants and flowers from around the world.

In the afternoon, head to Busch Stadium and see where the Saint Louis Cardinals baseball team plays. Near the stadium is Ballpark Village, which is full of restaurants and bars. There’s usually live music in some of the bars, so it’s a good place to hang out and grab a drink.

If you have extra time, I also recommend exploring the local shops in the Central West End and taking a stroll in Forest Park. Forest Park is full of plants and animals native to Missouri, and it’s also the home of the St. Louis Science Center and the Art Museum.

saint louis stadium - driving route 66

Day 6: St. Louis to Springfield, Missouri

This Route 66 itinerary then continues on to Springfield, Missouri. The drive takes around 4 hours, so I recommend heading out after breakfast. Along the way, make a stop in Sullivan to visit the Meramec Caves, a system of caves that stretches over 4 miles long. These caverns are the largest commercial caves in the state and are home to the rare Ozark cavefish, a species that can only be found in a few locations in the world. The history of the Meramec Caverns is also fascinating, with tales of use by Native Americans and later as a hideout for notorious outlaws like Jesse James. 

Once you arrive in Springfield, swing by the Route 66 Car Museum. It showcases a privately owned car collection owned by Guy Mace, who started collecting in 1990 when he bought his first Jaguar. His collection spans nearly 100 years of classic, one-of-a-kind vehicles. Each car has its own story. 

Where to Stay in Springfield, MO

Where to Eat in Springfield, MO

Route 66 Itinerary Day 7: Springfield to Tulsa, Oklahoma

It’s time to cross state lines again. After leaving Springfield, the next stop on this Route 66 itinerary is Tulsa. The journey takes about 3 hours, and it’s best to head out first thing in the morning to make the most of your day.

On your way to Tulsa, you can take a short detour to Foyil. It’s worth pulling off to see The Ed Galloway Totem Pole Park though. Ed Galloway is an Army veteran who retired in the 1930s and built totem poles as a hobby. The park’s main totem pole is 90ft tall!  The totem park was added to the National Register of Historic Places and is now owned and operated by the Rogers County Historical Society.

As you enter Tulsa, you’ll be greeted by a large Route 66 sign on an overhead bridge. You won’t miss it!

tulsa - route 66 road trip

Where to Stay in Tulsa, OK

Tulsa is a decent sized city, so there are plenty of hotels to choose from. Here are my recommendations:

Where to Eat in Tulsa

Oklahoma BBQ is famous in the US, so I definitely recommend trying some while you’re in Tulsa.

Route 66 Itinerary Day 8: Sightseeing in Tulsa

After arriving in Tulsa and getting settled in, I suggest taking part in its Route 66 traditions. A lot of sites along Route 66 have been abandoned over time, but Tulsa takes pride in its Route 66 history. If you head to 11th and Minigo Street, you can see the original Route 66 road and read the informational plaques to learn more about it.

Stop by and see the Blue Whale of Catoosa, just 20 minutes outside of Tulsa. The Blue Whale is a waterfront structure, and it has become one of the most recognizable attractions on Route 66. Hugh Davis built the Blue Whale in the early 1970s as a surprise anniversary gift to his wife Zelta, who collected whale figurines.

Back in Tulsa, you can visit the Route 66 Rising Sculpture at E. Admiral Place and S. Mingo Road. Artist Eric F. Garcia created this historic art piece, drawing inspiration from the Dust Bowl-era Depression, as well as the Mother Road’s beacon of hope. I also suggest visiting the Mother Road Market for some local food and a Route 66-themed mini golf course.

Another worthwhile destination is the Wonders of Wildlife National Museum and Aquarium, an immersive experience that takes visitors on a journey through the world’s most spectacular natural habitats, with over 35,000 live animals on display. 

tulsa - route 66 by car

Route 66 Itinerary Day 9: Tulsa to Amarillo, Texas

On day 9, continue your Route 66 road trip from Oklahoma to Texas. The drive takes about 5.5 hours, through desolate towns and stark landscapes. 

If you’re looking for something quirky to do, stop by Arcadia, OK, near Hiwassee Road. There’s a plaque here that commemorates where Paul McCartney once asked a local for directions while he was driving Route 66. It’s a little random, but it’s cool to think about how many people have made the same trip you’re making right now.

Then take a break at the Tower Station and U-Drop Inn Cafe in Shamrock. If you’ve seen the Disney movie Cars, this will probably look familiar to you. It was the inspiration for Ramone’s Body Shop in the movie!

route 66 to amarillo

road trip route 66

Where to Stay in Amarillo, TX

You can get a true Texas experience staying in Amarillo. Here’s are some top-notch hotels I recommend for all budgets:

Where to Eat in Amarillo, TX

Route 66 Itinerary Day 10: Sightseeing in Amarillo

Even though Amarillo isn’t as famous as some other stops on Route 66, it’s still worth spending a day here. There are some one-of-a-kind attractions that are fun for everyone!

One of the most popular is the Cadillac Ranch. There are a bunch of old Cadillac cars stuck in the ground, which is something you’ll probably only see near Route 66. The tradition is to bring some spray paint and make your own graffiti on them (don’t worry, it’s legal). 

You can also head out to Palo Duro Canyon State Park for some amazing views of nature. Hike or bike through towering red rock formations, steep canyons, and sweeping vistas of the surrounding landscape. For a unique and unforgettable experience, don’t miss the park’s outdoor musical drama, “Texas”, which tells the story of the state’s rich history through song and dance. If you’re more of a history buff, check out the Panhandle Plains Historical Museum. The People of the Plains exhibit is really interesting – it shows you how people have survived in Amarillo for the past 14,000 years.

cadillac ranch - stops along route 66

palo duro canyon - itinerary route 66

Day 11: Amarillo to Albuquerque, New Mexico

You’ll cross another state border on day 11 as you drive from Amarillo to Albuquerque. This drive is over 4 hours long, but you won’t see any traffic so it’s usually an easy drive.

To divide the drive time in half, I suggest making a pit stop in Santa Rosa, NM. This is where you can find the Blue Hole. It’s a swimming hole in the middle of the desert that’s 80 feet deep. You can even scuba dive in it! Once known as Blue Lake, it is one of seven sister lakes connected underground by a vast system of water.

There’s also a Route 66 Auto Museum in Santa Rosa you can wander through to pass some time. You can see a collection of over 30 vintage cars that have been restored by the owner,  James. Santa Rosa is proud to be on Route 66 and it definitely shows in this little town. 

route 66 road trip

Where to Stay in Albuquerque, NM

Albuquerque is the largest city in New Mexico, which means you have plenty of hotels to choose from. These are my top picks:

Where to Eat in Albuquerque, NM

Day 12: Albuquerque to Flagstaff, Arizona

It takes about 6 hours to drive this stretch of Route 66. To give yourself a break from driving, I recommend stopping off at a couple different places.  

The first is at the Petrified Forest National Park right on the original Route 66. Depending on how much time you want to spend here, you can drive to some of the overlooks or get out and explore some of the trails. I’d suggest taking the short walk (0.3) miles to Puerco Pueblo to see the petroglyphs.

Don’t miss Winslow, where you can see Meteor Crater, the breath-taking result of a collision between a piece of an asteroid traveling at 26,000 miles per hour and planet Earth approximately 50,000 years ago. What scientists have learned here has helped them unlock secrets of the formation of our solar system and the universe! Once you’re there, you can take a tour of the rim and visit the Barringer Space Museum to learn more about the phenomenon.

winslow arizona - planning a trip on route 66

winslow meteor crater - route 66 itinerary 14 days

Where to Stay in Flagstaff, AZ

Where to Eat in Flagstaff, AZ

Day 13: Flagstaff to Barstow, California

Day 13 takes you to the final state on your Route 66 itinerary — California. This drive takes around 5 hours. On your way, I suggest making a stop in Calico to visit the Calico Ghost Town Regional Park. Calico is an old West mining town that has been around since 1881 and was abandoned in the mid-1890s after silver lost its value. The town that once gave miners a good living lost its hustle and became a “ghost town. It’ll give you a real flashback to the past! 

barstow california - route 66 road trip itinerary

Where to Stay in Barstow, CA

Where to Eat in Barstow, CA

Route 66 Itinerary Day 14: Barstow to Santa Monica, CA

For the final leg of this 2-week Route 66 itinerary, you’ll drive from Barstow to Santa Monica, which only takes about 2 hours. Be prepared to deal with some traffic once you hit the Los Angeles area though, especially if you drive during the afternoon.

In my opinion, the best way to end your journey is on Santa Monica Pier. The pier is home to a historic carousel, an aquarium, an amusement park with a Ferris wheel, and several restaurants and shops.Have a late lunch at Mariasol Cocina Mexicana, the Mexican restaurant at the very end of the pier. Then stroll along the famous Third Street Promenade, a pedestrian-only shopping and dining district that features street performers, live music, and a range of retail options.

Another popular spot in Santa Monica is Muscle Beach, a historic outdoor gym that has been a popular training ground for bodybuilders and fitness enthusiasts since the 1930s.  If you’re planning to spend a few days in the City of Angels, check out my Los Angeles itinerary.

route 66 itinerary - santa monica california

Enjoy Your Route 66 Road Trip

That’s it! We’ve reached the end of the ultimate USA road trip! Hopefully this Route 66 itinerary has helped you plan the ultimate drive on Route 66! Feel free to bookmark it or print it out and follow it as you go along. If you stop at any of these places on the list, tell me what you thought of them in the comments. 

Here are more road trip itineraries I’ve written:

Disclaimer: This post contains affiliate links to companies that I use and trust. I’ll get a small commission when you click on those links, at NO EXTRA COST TO YOU.

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