Route 66 (Illinois & Missouri) 14-Day Trip Itinerary

Arrive in Chicago & Car Pickup

Arrive at Chicago O'Hare International Airport (ORD), pick up your rental car, and head into the city.

Prepare for your ultimate road trip adventure!

Begin Route 66

Stand at the official starting point of Historic Route 66 in Chicago.

This is where your unforgettable journey along the Mother Road truly begins.

Capture some photos at the 'Begin Route 66' sign. Explore the surrounding area of downtown Chicago.

Millennium Park Exploration

Visit Chicago's iconic Millennium Park, home to Cloud Gate ('The Bean'), Crown Fountain, and Lurie Garden.

A great spot for scenic views and photography.

Perfect for capturing unique reflections and cityscapes. Wear comfortable shoes as you'll be walking quite a bit.

Deep Dish Pizza Dinner

Savor a classic Chicago deep-dish pizza, a culinary must-do when in the city.

Drive to Joliet

Begin your scenic drive southwest out of Chicago towards Joliet, the first major stop on Illinois Route 66.

Old Joliet Prison Tour

Explore the historic Old Joliet Prison, famous from 'The Blues Brothers' movie and a significant landmark.

Check tour availability and book in advance, especially for guided tours. (Not an enriched booking, general suggestion)

Pontiac Route 66 Museum

Visit the Illinois Route 66 Hall of Fame and Museum in Pontiac, home to a vast collection of memorabilia, vintage vehicles, and informative exhibits.

Don't miss the many vibrant murals around Pontiac, especially the large Route 66 shield mural.

Lincoln Home National Historic Site

Explore the historic home of Abraham Lincoln, the only house he ever owned, offering a glimpse into his life before the presidency.

Visitor center provides free timed-entry tickets for house tours. Arrive early or check online for availability.

Dinner in Springfield

Enjoy dinner at a local Springfield restaurant, perhaps trying a 'Horsehoe Sandwich' - a local specialty.

Railsplitter Covered Wagon

Visit the world's largest covered wagon, complete with a giant Abraham Lincoln statue reading a book inside.

A classic Route 66 quirky photo op!

Don't forget your camera for this iconic roadside attraction. Free to visit.

Paul Bunyan Hot Dog Statue

Discover another giant statue, the Paul Bunyan holding a hot dog, a whimsical piece of Americana in Atlanta, Illinois.

Part of the 'Muffler Man' collection of roadside giants. Free to visit.

Funks Grove Pure Maple Sirup

Stop at the historic Funks Grove for a taste of authentic pure maple sirup, produced using traditional methods.

A sweet detour offering a taste of local history and flavor. Small entry fee or purchase may apply.

Chain of Rocks Bridge

Walk or drive across a section of the historic Chain of Rocks Bridge, known for its unique 22-degree bend and scenic views over the Mississippi River.

The bridge is now pedestrian and bicycle-only, offering great photo opportunities. Park on the Illinois side.

Check into St. Louis Hotel

Arrive in St.

Louis and check into your accommodation for the next two nights.

Dinner in St. Louis

Enjoy your first evening in St.

Louis with dinner at a local eatery.

Gateway Arch National Park

Ascend to the top of the iconic Gateway Arch for breathtaking views of St.

Louis and the Mississippi River. Explore the museum at its base.

Book tram tickets to the top in advance, especially during peak times. Allow time for security.

Lunch in Downtown St. Louis

Enjoy lunch near the Gateway Arch, perhaps trying some St.

Louis-style BBQ.

City Museum Adventure

Experience the unique City Museum, an eclectic mix of children's museum, funhouse, and architectural marvel.

It's a playground for all ages!

Wear comfortable clothes and shoes as you'll be climbing, sliding, and exploring. Very quirky and fun!

Evening at The Delmar Loop

Explore The Delmar Loop, one of America's great streets, known for its eclectic shops, restaurants, music venues, and the St.

Louis Walk of Fame.

Grab dinner here and enjoy the vibrant atmosphere. Plenty of unique places for a fun evening.

Drive to Meramec Caverns

Depart St. Louis and head west on Route 66 towards Stanton, Missouri, home of Meramec Caverns.

Meramec Caverns Tour

Explore Missouri's largest cave system, Meramec Caverns, a historical hideout of Jesse James and a classic Route 66 attraction.

Tours are guided and last about 1.5 hours. Wear comfortable shoes and a light jacket as caves are cool.

Route 66 Mural City (Cuba, MO)

Drive through Cuba, Missouri, known as 'Route 66 Mural City,' and admire its numerous historic and artistic murals depicting the town's history and Route 66.

Pull over safely to take photos of the murals. It's a great blend of local culture and roadside art.

Route 66 Car Museum

Immerse yourselves in automotive history at the Route 66 Car Museum, showcasing a fantastic collection of classic cars and memorabilia.

A must-see for car enthusiasts and anyone interested in vintage Americana. Check opening hours before visiting.

Dinner in Springfield, MO

Enjoy dinner in Springfield, Missouri, the 'Birthplace of Route 66'.

Meramec Caverns Exploration

Descend into the Meramec Caverns, a historic underground wonder and former hideout for Jesse James, marveling at the impressive stalagmites and stalactites.

Guided tours typically run frequently. Check their website for specific tour times. The caverns maintain a cool temperature, so a light jacket is recommended.

Classic Diner Lunch

Enjoy a classic American diner lunch at a local Route 66 establishment, experiencing the nostalgia of the Mother Road.

Look for diners like Missouri Hick Bar-B-Q or the Elbow Inn Bar & BBQ for authentic Route 66 vibes.

World's Largest Rocking Chair

Stop for a photo opportunity with the World's Largest Rocking Chair in Fanning, a true example of Route 66 kitsch.

A fun, quick stop for unique photos. There's also a gift shop nearby.

Route 66 Car Museum

Explore the Route 66 Car Museum, home to a diverse collection of classic cars, movie vehicles, and other unique automobiles, perfect for automotive enthusiasts.

A great stop for fans of classic cars and Americana. Check their opening hours as they can vary.

Dinner in Springfield

Enjoy dinner at a local restaurant in Springfield, Missouri.

Springfield offers a variety of dining options from casual to more upscale.

Drive to Tulsa, Oklahoma

Continue your journey west on Route 66 from Springfield, MO, heading towards the vibrant city of Tulsa, Oklahoma.

Enjoy the scenic drive.

This stretch of Route 66 offers a mix of rural landscapes and small towns.

Art Deco Tulsa Walk

Begin your exploration of Tulsa's stunning Art Deco architecture with a leisurely walk through the downtown area.

Many beautiful buildings like the Philcade Building and the Boston Avenue Methodist Church are examples of this architectural style.

Visit The Cave House

Discover The Cave House, a unique and quirky attraction with an intriguing history, known for its unusual architecture and stories.

This historic and eccentric home is often described as a 'hobbit hole' or 'flintstone house'. Tours are typically by appointment or limited hours, so check ahead.

Holy Family Cathedral

Visit the Holy Family Cathedral, an architectural marvel and significant landmark in Tulsa known for its beautiful stained glass and intricate design.

Remember to be respectful as it is an active place of worship. Check for visitor hours.

Philtower Building Photo Stop

Admire the stunning exterior of the Philtower Building, another magnificent example of Art Deco architecture in Tulsa.

This building is a highlight of Tulsa's skyline and offers great photographic opportunities.

Dinner in Tulsa

Savor dinner in Tulsa, with many options ranging from casual eateries to upscale dining.

Consider the Blue Dome Entertainment District for a lively atmosphere and diverse restaurant choices.

Creek Nation Council Oak Park

Start your day with a peaceful visit to Creek Nation Council Oak Park, a site of historical significance for the Muscogee (Creek) Nation.

A quiet and contemplative space to learn about Native American history in Oklahoma.

Drive to Oklahoma City

Embark on a scenic drive from Tulsa to Oklahoma City, continuing your Route 66 journey.

This stretch of interstate mostly bypasses the historic Route 66, but segments can be found by taking local exits.

Lunch in Oklahoma City

Enjoy lunch in Oklahoma City, perhaps in the Bricktown district or downtown.

Numerous dining options are available to suit all tastes.

Oklahoma City National Memorial

Visit the poignant Oklahoma City National Memorial & Museum, a tribute to the victims, survivors, rescuers, and all who were affected by the 1995 bombing.

Allow ample time for reflection at the outdoor memorial and for the museum exhibits. It's a powerful and moving experience.

Explore Bricktown Entertainment District

Wander through the historic Bricktown Entertainment District, known for its renovated warehouses, canal rides, and lively atmosphere.

Consider a water taxi tour along the canal for a different perspective of the area.

Dinner in Bricktown

Enjoy dinner at one of the many restaurants in the vibrant Bricktown district.

Choose from a wide variety of cuisines in this popular area.

Drive to Clinton, Oklahoma

Depart Oklahoma City and drive west on historic Route 66 towards Clinton, the next stop on your journey.

This section of Route 66 offers a glimpse into classic roadside architecture.

Oklahoma Route 66 Museum

Immerse yourselves in the history of Route 66 at the Oklahoma Route 66 Museum, featuring interactive exhibits and themed rooms.

The museum offers a fantastic journey through the route's history in Oklahoma. Allow plenty of time to explore all the galleries.

Lunch in Clinton

Enjoy lunch in Clinton before continuing your exploration of Oklahoma's Route 66.

Look for local diners offering classic American fare.

National Route 66 Museum

Visit the National Route 66 Museum in Elk City, offering another comprehensive look at the history and culture of the Mother Road.

This museum is part of the Elk City Museum Complex, which includes several other attractions covering local history.

Drive to Shamrock, Texas

Cross the state line into Texas and arrive in the charming town of Shamrock, home to iconic Route 66 landmarks.

Keep an eye out for the 'Welcome to Texas' signs and the changing landscape.

U-Drop Inn Photo Opportunity

Photograph the magnificent Art Deco U-Drop Inn, a historic gas station and restaurant that is a true gem of Route 66 architecture.

This landmark is beautifully restored and illuminated at night, making for excellent photos. It also serves as the city's visitor center.

Dinner in Shamrock

Enjoy dinner at a local restaurant in Shamrock, Texas.

Experience small-town Texas hospitality.

Morning in Shamrock

Take some final morning photos of the U-Drop Inn or explore any other small attractions in Shamrock before heading further west.

The U-Drop Inn is often open as a visitor center during the day, offering a chance to see the interior.

Drive to Amarillo, Texas

Embark on the final stretch of this segment, driving from Shamrock to the major city of Amarillo in the Texas Panhandle.

The landscape transforms into the vast, open plains characteristic of the Texas Panhandle.

Lunch in Amarillo

Enjoy a hearty lunch in Amarillo, perhaps trying some authentic Texas BBQ.

Amarillo is known for its steakhouses and Texan cuisine.

Cadillac Ranch

Visit the iconic Cadillac Ranch, an art installation where ten Cadillac cars are half-buried nose-first in the ground.

Bring spray paint to leave your mark!

This is a must-see quirky stop and a fantastic photo opportunity. The cars are constantly re-painted by visitors, so it's always changing.

Amarillo's Route 66 Historic District

Explore the 6th Street Historic District in Amarillo, a vibrant stretch of Route 66 filled with antique shops, diners, and unique boutiques.

This district is perfect for souvenir shopping and soaking in more Route 66 nostalgia.

Dinner in Amarillo

Enjoy your evening dinner in Amarillo, marking the end of this segment of your Route 66 journey.

Consider 'The Big Texan Steak Ranch' for a truly over-the-top Route 66 dining experience.

Cadillac Ranch

Start your day with a visit to the iconic Cadillac Ranch, an art installation where ten Cadillac automobiles are buried nose-first in the ground.

Bring spray paint to leave your mark!

Free entry. Located on private land, but accessible to the public. Expect some dirt/mud.

Historic Route 66 Midpoint

Stop at the official 'Midpoint of Route 66' in Adrian, Texas.

Visit the Midpoint Cafe, a classic diner known for its 'ugly crust pie' and grab a photo at the iconic sign.

Great spot for souvenirs and a classic Route 66 meal. Often busy with fellow road trippers.

Tucumcari & Route 66 Monument

Explore the vibrant neon signs and vintage motels of Tucumcari, New Mexico.

Visit the Route 66 Monument and soak in the town's classic Americana atmosphere.

Historic Route 66 Motel Photo Stop

A quick photo stop at the Historic Route 66 Motel, an excellently preserved mid-century modern motel that captures the spirit of the Mother Road.

Even if not staying, it's a great photo opportunity. Booking: https://www.tripadvisor.com/Hotel_Review-g47242-d1007465-Reviews-Historic_Route_66_Motel-Tucumcari_New_Mexico.html?m=66827

Drive to Albuquerque

Enjoy the scenic drive from Tucumcari to Albuquerque, the largest city in New Mexico, offering a blend of Native American, Hispanic, and Anglo cultures.

Dinner in Old Town

Savor dinner at a traditional New Mexican restaurant in Albuquerque's historic Old Town, known for its unique architecture and vibrant atmosphere.

Explore Albuquerque Old Town

Take a morning stroll through the historic Old Town of Albuquerque, browsing unique shops, art galleries, and admiring the Spanish colonial architecture.

Plenty of souvenir shops and local artisan crafts. The main plaza is a lovely place to relax.

Drive to Petrified Forest

Embark on a scenic drive from Albuquerque, New Mexico into Arizona, heading towards the Petrified Forest National Park.

Petrified Forest National Park

Discover the vibrant colors of the petrified wood logs and the Painted Desert at this unique national park.

Stop at various overlooks and short trails.

The park entrance fee covers all passengers in a single vehicle. Plan for a few hours to drive through and stop at key viewpoints.

Standin' on the Corner Park

Visit the famous 'Standin' on the Corner' Park in Winslow, Arizona, inspired by the Eagles' song 'Take It Easy'.

Take a photo with the statue and the mural.

A fun, quick stop for music lovers and Route 66 enthusiasts.

Drive to Williams, AZ

Continue your drive to Williams, Arizona, known as the 'Gateway to the Grand Canyon' and one of the best-preserved Route 66 towns.

Dinner in Historic Williams

Enjoy dinner at one of the classic diners or restaurants in downtown Williams, soaking in the nostalgic Route 66 atmosphere.

Grand Canyon South Rim

Embark on a breathtaking journey to the Grand Canyon South Rim.

Explore iconic viewpoints like Mather Point, Yavapai Point, and Grandview Point. Allow ample time for shuttle rides and short walks.

The Grand Canyon entrance fee covers all passengers in a single vehicle. Dress in layers, as temperatures can vary greatly. Consider a picnic lunch.

Drive to Kingman, AZ

Begin your journey southwest towards Kingman, Arizona, an important stop on historic Route 66.

Historic Route 66 Museum

Visit the Historic Route 66 Museum, located in the Powerhouse Visitor Center, to learn about the history and culture of the Mother Road.

An excellent museum with engaging exhibits. Tripadvisor booking link: https://www.tripadvisor.com/Attraction_Review-g31259-d1657283-Reviews-Historic_Route_66_Museum-Kingman_Arizona.html?m=66827

Oatman Ghost Town

Drive the winding Oatman Highway through the Black Mountains to the authentic Old West ghost town of Oatman, famous for its wild burros roaming the streets.

Be prepared for narrow, winding roads. The burros are friendly but respect their space.

Drive to Barstow, CA

Cross the California border and drive into the Mojave Desert towards Barstow, a classic Route 66 stop.

Dinner in Barstow

Grab a late dinner in Barstow, reflecting on the day's journey through Arizona's varied landscapes.

Elmer's Bottle Tree Ranch

Visit Elmer's Bottle Tree Ranch, a unique and quirky roadside attraction featuring hundreds of bottle trees created by Elmer Long.

A fascinating and photogenic stop showcasing classic Route 66 eccentricity.

Drive to Santa Monica

Embark on the final leg of your Route 66 journey, driving from the Mojave Desert into the bustling greater Los Angeles area, ending at the Pacific Coast.

Be prepared for increased traffic as you approach Los Angeles.

Santa Monica Pier & Lunch

Arrive at Santa Monica Pier, the official 'End of the Trail' for Route 66.

Enjoy the ocean views, explore the pier attractions, and grab lunch with a view.

Walk to the iconic 'Route 66 End of the Trail' sign. There are several casual dining options on the pier.

Relax on Santa Monica Beach

Spend some time relaxing on the sandy shores of Santa Monica Beach, soaking in the Pacific Ocean atmosphere after your long cross-country drive.

A perfect way to unwind and reflect on your incredible journey. Consider renting bikes or exploring the boardwalk.

Farewell Dinner in Santa Monica

Celebrate the completion of your epic Route 66 road trip with a memorable farewell dinner at a restaurant in Santa Monica.

Choose from a wide array of dining options, from casual to upscale, many with ocean views.

Trip Conclusion

Your incredible 14-day Route 66 adventure officially concludes in Santa Monica.

Depart for your next destination or relax for the evening.