The Best 2 Week Route 66 Road Trip Itinerary

Discover the best comprehensive itinerary for an incredible 2-week journey along America’s Route 66.
The Best Route 66 Road Trip Itinerary: 2 Weeks. Photo: Mick Haupt | Unsplash

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Route 66 is the mother of all roads in the United States. Spanning from Chicago to Los Angeles, it’s the apex of the American cross country road trip, passing by more historical buildings, fun attractions, scenic landscapes, novelty shops, and neon signs than any other in the nation.

And now, it’s time to complete your own journey along Route 66. But, where do you start? What will you see along the way? What should you do and where should you stay?

There are tons of questions to ask, but believe me, I’ve got you covered. Let’s check out this comprehensive itinerary for 2 weeks along Route 66.

Day 1: Chicago, Illinois

You’ve arrived in Chicago and your grand Route 66 tour will commence tomorrow. While you’re here, do more relaxing than exploring, as you’ll need to conserve your energy for the long drives ahead.

Welcome to Chicago! Photo: Pedro Lastra | Unsplash

What to Do and See in Chicago, Illinois?

Check out green spaces, fountain, public art, and the city’s towering downtown skyscrapers at Millennium Park.

You can also take a 2-hour cruise along Chicago River and pay a visit to the Skydeck Chicago observation deck on the 103rd floor of Willis Tower.

There’s Chicago Botanical Garden, Museum of Illusions, the Art Institute of Chicago and Navy Pier.

And if you’re up for it, grab the chance to watch a live Cubs Game at Wrigley Field. But remember, don’t do too much because tomorrow’s the big day!

Where to Eat in Chicago, Illinois?

  • Pequod’s Pizzeria
  • J.P. Graziano Grocery and Sub Shop
  • Green Street Smoked Meats
  • Portillo’s Hot Dogs

Where to Stay in Chicago, Illinois?

  • $$$ – London House Chicago
  • $$ – The Godfrey Hotel Chicago
  • $ – Freehand Chicago

Day 2: Chicago to St. Louis

Your big day here is here! Let’s begin your journey by exploring some Route 66 attractions and head out to St. Louis.

Starting point for Route 66 in Chicago. Photo: Walter Martin | Unsplash

What to Do and See in Chicago, Illinois?

Let’s start your epic Route 66 adventure by grabbing a photo opportunity at the Historic Route 66 Begin sign located across from Chicago Art Institute.

En Route to St. Louis

Next, make a stop at Joliet Area Historical Museum and Route 66 Welcome Center for a look at memorabilia and nostalgic artifacts involving the world-famous road.   

Afterwards, land at the 30 ft. tall Gemini Giant in Wilmington. The popular statue was once used to serve as a prop advertisement for the “Muffler Man” in the 1960s. 

Gemini Giant. Photo: steppinstars | Pixabay

When you’re finished, head to the Polk-a-Dot Drive-In in Braidwood. The diner is renowned for its life-sized statues of famous celebrities (real and cartoon) that include Elvis, Marilyn Monroe, and Betty Bop. Plus, you’ll also find a 9-foot-tall statue of Elvis playing a guitar, as well as an impressive statue of Superman outside of a phone booth, nearby. 

Later, stop by the Route 66 Illinois Hall of Fame and Museum in Pontiac for photo ops, guides, artifacts, and everything else related to Route 66. If there’s time, pay a visit to the Pontiac Oakley Automobile Museum, too.

When you hit Springfield, check out the architecture of the Illinois State Capital building, the Lincoln Presidential Library and Museum, and see the house where America’s 16th president grew up at the Lincoln Home National Historic Site.

Where to Eat en route to St. Louis?

  • Lou Mitchells
  • Henry’s Drive-In
  • Joliet Kicks on 66
  • Pol-a-Dot Drive-In
  • Cozy Drive In

Day 3: St. Louis, MO

The next two days are all about exploring top attractions along Route 66 in Missouri, primarily in St. Louis and Springfield. You’ll go from visiting world-famous landmarks to the inside of mineral caves. Let’s do it!

Chain of Rocks Bridge. Photo: Chris Yunker | Flickr

What to Do and See in St. Louis?

While in St. Louis on Day 3, begin the day with a visit to Chain of Rocks Bridge on Route 66. Then make a leisure trip to City Museum, which is fun playground for all-ages. There are tunnels, caves, slides, art activities, sculptures, a tree house, and tons more.

Next, find time to unwind at Forest Park, a sprawling 1,326-acre park also home to the St. Louis Zoo and Missouri History Museum. Feel free to explore either one of those as well.

By late afternoon, head over to the iconic 630 ft. tall St. Louis Gateway Arch. There, you’ll want to explore its fascinating museum, and best of all, take a Ferris Wheel-styled tram all the way to the top for an incredible bird’s eye view of the city. This is a can’t miss!

From the evening onward, take a cruise down the St. Louis Riverfront. Stroll the city streets and take in the sights around the Old Courthouse building. You’ll also find plenty of eateries and bars around the Laclede’s Landing area next to Gateway National Park and lining Busch Stadium.

St. Louis’ Gateway Arch in the distance. Photo: Brittany Butler | Unsplash

Where to Eat in St. Louis?

  • Pappy’s Smokehouse
  • Stacked STL
  • Drunken Fish
  • Louie

Where to Stay in St. Louis?

  • $$$ – Hotel Lumiere at the Arch
  • $$ – Drury Plaza Hotel St. Louis
  • $ – OYO Hotel St. Louis Downtown City Center

Day 4: Springfield, MO

Continue your Route 66 journey in Missouri with a look at fun attractions in Springfield.

Rest Haven is a historic landmark on Route 66. Photo: Robert Linder | Unsplash

What to Do and See in Springfield?

Start the day with an early morning trip to the 4.6-mile, hundreds-of-millions-of-years-old limestone Meramec Caverns in Stanton, which is the most visited cave system in all of Missouri. When you’re finished, make sure to swing by the Jesse James Wax Museum, too.

When you arrive in Springfield, visit the Route 66 Springfield Visitor Center for information and brochures. Next, explore Wilson’s Creek National Battlefield, which hosted the first major American Civil War Battle on the westside of the Mississippi River. 

If you’re a car buff, the Route 66 Car Museum features classic and sports automobiles.

And if you skipped out on Meramec Caverns earlier in the day, this would be the perfect time to visit Springfield’s Fantastic Caverns and/or Crystal Cave. You’ve got plenty of time to tour the city’s natural wonders!

Meramac Caverns. Photo: Paul Barker Hemings | Flickr

Where to Eat in Springfield?

  • Missouri Hicks BBQ
  • Metropolitan Grill
  • Pappo’s Pizzeria
  • Black Sheep Burgers & Shakes

Where to Stay in Springfield?

  • $$$ – Towne Place Suites
  • $$ – University Plaza Hotel and Convention Center
  • $ – Sleep In Springfield South 160

Day 5: Kansas to Oklahoma

For Day 5, you’ll be driving through only 13-miles of Kansas and heading down to Tulsa, Oklahoma. Enjoy the sights, sounds, and cuisine of the Midwest city.

Cars on the Route. Photo: Marada | Flickr

What to Do and See in Kansas?

Kansas only contains about a 13-mile stretch of Route 66. With that, here’s a list of popular places you should stop and see along the way.

  • Cars on the Route – A gift shop. Inspired the movie Cars by Pixar
  • Old Riverton Store
  • Marsh Arch Bridge (Rainbow Bridge)
  • Schermerhorn Park

On the way to Tulsa, stop for a photo op at Ed Galloway’s Totem Pole Park in Foyil. Next, pay a visit to the iconic Blue Whale attraction in Catoosa.

For the rest of Day 5 and Day 6 in Tulsa, there are plenty of Route 66 attractions to check out as well as popular things to do and see local to the city.

En Route to Tulsa

Take a look at popular Route 66 roadside attractions in Tulsa that include Buck Atom’s Cosmic Curios, Decopolis Discovitorium, the iconic Meadow Gold neon sign, the Route 66 Historical Village, Cyrus Avery Centennial Plaza, and the Golden Driller Statue.

Meadow Gold. Photo: Mick Haupt | Unsplash

What to Do and See in Tulsa?

You’ll want to visit the mysterious Center of the Universe to observe the puzzling sound phenomenon that takes place there.

Enjoy scenic riverfront views at Gathering Place, a 70-acre hybrid park. If you’re traveling Route 66 during the summer, escape the heat by getting splashed at Safari Joe’s H2O water park.

Feel free to check out a local show at the Tulsa Performing Arts Center, which hosts Tulsa Ballet, Tulsa Opera, and Tulsa Symphony.

In the late night, hit the Hard Rock Hotel and Casino to try your luck at gambling.

Center of the Universe. Photo: Jane Hammons | Flickr

Where to Eat in Tulsa?

  • Fat Guys Burger Bar
  • Ranch Grando Mexican Food
  • Evelyn’s Soul Food Cuisine
  • Leon’s Smoke Shack BBQ

Where to Stay in Tulsa?

  • $$$ – Ambassador Hotel Tulsa
  • $$ – Springhill Suites by Marriott Tulsa
  • $ – Expo Inn

Day 6: Oklahoma City

Today you’ll be heading to Oklahoma City for a grand tour of Route 66 attractions and popular local experiences.

Pops 66 Soda Ranch. Photo: Allison Meier | Flickr

What to Do and See in Oklahoma City?

First up, on your way towards OKC, stop and grab a photo of the 66-foot tall LED soda bottle at Pops 66 Soda Ranch. You’ll also want to visit OK County 66, or John’s Place, to see the quirky collection of Route 66 related art and memorabilia.  

When you land in OKC, pay a visit to the Gold Dome, a golden geodesic dome and historical landmark that’s been around since 1958.

Check out artwork and artifacts of the National Cowboy and Western Heritage Museum. Next, take a 40-minute Bricktown Water Taxi down Bricktown Canal. Afterwards, ride the Wheeler Ferris Wheel at Wheeler District.

You also have the option of spending most of the day at Frontier Amusement Park if you have the time and energy for amusement rides versus visiting multiple attractions.

Bricktown Water Taxi. Photo: Kevin | Flickr

Where to Eat in Oklahoma City?

  • Cattlemen’s Steakhouse
  • Tucker’s Onion Burgers
  • Cheever’s Café
  • S & B’s Burger Joint

Where to Stay in Oklahoma City?

  • $$$ – Ambassador Hotel Oklahoma City
  • $$ – Candlewood Suites
  • $ – Econo Lodge Inn & Suites

Day 7 – 8: Amarillo, Texas

For Day 7, you’ll be driving south along Route 66 in Oklahoma and arriving in Texas. During Day 8, you’ll be exploring Route 66 landmarks and attractions in and around Amarillo.

Cadillac Ranch in Amarillo. Photo: Heidi Kaden | Unsplash

En Route to Amarillo

En route to Amarillo, check out the Route 66 Museum in Clinton, Oklahoma, which offers details, artifacts, and sets regarding the road’s special history. Or, wait for the larger National Route 66 and Transportation Museum.

You’ll also want to explore Conoco Tower Station, the Leaning Tower of Britten, and the VW Bug Ranch in Conway, Texas. There, you’ll find five graffiti-laced Volkswagen Beetles partly buried in the ground.

What to Do and See in Amarillo?

You’ll want to swing by the larger Cadillac Ranch, which is a very popular stop on Route 66 consisting of 10 Cadillacs partly buried in the ground. Plus, nearby lies the towering 2nd Amendment Cowboy statue

Make sure you visit the Amarillo Railroad Museum, Kwahadi Museum of the American Indian, and/or Panhandle-Plains Historical Museum for local educational history and overview.

You can also ride rollercoaster and amusement rides at Wonderland Amusement Park and see animals at the Amarillo Zoo.

What you’ll really want to do, nonetheless, is save enough time to visit and hike Palo Duro Canyon State Park, which is the 2nd largest canyon in the US.

Palo Duro Canyon State Park. Photo: K. Mitch Hodge | Unsplash

Where to Eat in Amarillo?

  • Big Texan Steak Ranch and Brewery
  • The Goldenlight Café and Cantina
  • Fire Slice Pizzeria
  • The Drunken Oyster

Where to Stay in Amarillo?

  • $$$ – Embassy Suites by Hilton Amarillo Downtown
  • $$ – Drury Inn & Suites Amarillo
  • $ – Big Texan Motel

Day 9 – 10: Albuquerque, New Mexico

You’ll be spending Day 9 and 10 driving from Texas and landing in Albuquerque, New Mexico, where you’ll start to enjoy west coast attractions along Route 66. 

Midpoint sign. Photo: Larry Syverson | Flickr

En Route to Albuquerque

Make a stop at the official halfway point sign for Route 66, located in Adrian, Texas. When you reach Tucumcari, New Mexico, pay a visit to Tepee Curios gift shop. You can also check out the Route 66 Auto Museum in Santa Rosa for yet another look at classic and sports automobiles. 

What to Do and See in Albuquerque?

Explore the Indian Pueblo Cultural Center to learn about Native American history and culture. Other educational centers to check out include Albuquerque Museum and the National Museum of Nuclear Science and History.

Unwind with wine and scenic views at Gruet Winery and Tasting Room. Try your luck at gambling with a trip to Route 66 Casino Hotel, or tour locations used in the hit series Breaking Bad with Breaking Bad RV Tours.

Although there are tons of things to do in Albuquerque, I must insist that you not leave without squeezing in time for at least one of these next adventures. For one, take the Sandia Peak Tramway to the 10,378-fot crest of Sandia Mountains for an awesome panoramic view of the city.

And two, you can schedule a sunrise or sunset hot air balloon ride over natural terrain on the outskirts of the city using Rainbow Ryders.

Sandia Peak Tramway. Photo: Stephanie Klepacki | Unsplash

Where to Eat in Albuquerque?

  • Central Food Hall
  • Sawmill Market
  • Sadie’s
  • Route 66 Diner

Where to Stay in Albuquerque?

  • $$$ – Hotel Albuquerque at Old Town
  • $$ – La Quinta Inn & Suites
  • $ – Quality Inn Suites Downtown

Day 11 – 12: Flagstaff, Arizona

Over the next two days, you’ll be taking an incredibly scenic drive from Albuquerque into Flagstaff, Arizona. Once there, you’ll pay a visit to Route 66 attractions and local experiences.

Painted Desert. Photo: 127071 | Pixabay

En Route to Flagstaff

Grab a photo op in front of the Continental Divide Elevation sign, which marks rainfall in the west drains into the Pacific, and in the East, into the Atlantic.

Later, make stops at the different overlooks featured in Petrified Forest National Park and Painted Desert. There, you’ll find hundred-of-millions-years old tree logs and colorful geological formations. Visitors can also join a ranger and experience guided hikes and cultural presentations.  

Next, stop by the Jack Rabbit Trading Post which is an official roadside attraction on Route 66.

What to Do and See in Flagstaff?

While in Flagstaff, take a walking tour of the city using the Walk This Talk audio guide, which covers the history of Route 66 in downtown and explains significant signs, events, and people across the city. This starts at the Flagstaff Visitor’s Center.

Plus, check out the Museum Club and the neon signs at Western Hills Motel. You can explore the Arboretum at Flagstaff and Heritage Square.  

The iconic Western Hills Motel. Photo: Kevin | Flickr

Since Flagstaff’s landscape is perfect for outdoor adventure, feel free to explore these “nearby” opportunities if you’ve got enough time and energy:

  • Grand Canyon National Park
  • Walnut Canyon National Monument
  • Hoover Dam
  • Meteor Crater Natural Landmark
  • Antelope Canyon

Where to Eat in Flagstaff?

  • Delhi Palace Cuisine of India
  • Tinderbox kitchen
  • Simply Delicious Café Daily Fare

Where to Stay in Flagstaff?

  • $$$ – Double Tree by Hilton Hotel Flagstaff
  • $$ – Hotel Monte Vista
  • $ – The L Motel

Day 13 – 14: California

For you last two days, you’ll be venturing into California and finalizing your trip on Route 66 in Los Angeles.

Santa Monica Pier. Photo: BKD | Pixabay

En Route to Los Angeles

The west coast’s landscape is remarkable. You’ll see long stretches of rugged mountains and bright blue skies as you pass through the Backcountry Byway and Mohave Desert between small towns like Kingman, AZ, Oatman, AZ, and Needles, CA.

When you hit Barstow, check out the historic facilities on Main Street. There’s a Barstow Route 66 Museum and you’ll definitely want to visit Elmer’s Bottle Tree Ranch.

Elmer’s Bottle Tree Ranch. Photo: Anthony Quintano | Flickr

After arriving in San Bernardino, explore the historical California Theatre. You can also swing by the original McDonald’s on North E Street.

What to Do and See in Los Angeles?

You’ve finally made it! There are tons of fun things to do in Los Angeles. You’ll end your trip at Santa Monica Pier, so make sure to spend a good amount of time at Santa Monica Beach. You can also explore Venice Beach and take a scenic drive along Pacific Coast Highway.

Aerial shot of Los Angeles. Photo: Henning Witzel | Unsplash

Swing by the shops along Hollywood Boulevard and go hiking along Runyon Canyon. Take a ride on the see-through slide at OUE Skyspace in downtown. Do some shopping at the Santee Alley, Grove, and on Melrose. Head to any one of several theme parks, including Disneyland, Six Flags, Universal Studios, and Knott’s Berry Farm.

Make stops at the LA County Museum of Art, Griffith Observatory, Getty Museum. Watch a live sports game at the Arena or Dodger Stadium. Just make sure you end your 2-week Route 66 trip on a high note!

Where to Eat in Los Angeles?

  • Grand Central Market
  • Pink’s Hot Dog Stand
  • Bubba Gump
  • In N’ Out Burger

Where to Stay in Los Angeles?

  • $$$ – The Beverly Hilton
  • $$ – Galaxy Inn
  • $ – Freehand Los Angeles

Final thoughts:

Route 66 ends in Santa Monica. Photo: Terence Starkey | Unsplash

So, there you have it—the best itinerary for traveling along Route 66 over 2 weeks. What are you most excited to see? Will you start in Chicago or maybe halfway, like in New Mexico? Are there local foods you want to try along the way?

I can’t wait for you to start your adventure. And when you do, just make sure to take plenty of photos and videos to share with the world. Safe and happy travels!


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