Arrive into O’Hare International Airport, Chicago. Collect your bags and transfer independently to your downtown hotel.

This evening you are at leisure to enjoy some of the many culinary delights in Logan Square, Wicker Park, or West Loop.

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You may like to start your day with a visit to Millennium Park, where you can marvel at the iconic Cloud Gate sculpture (commonly known as “The Bean”) and stroll through the serene Lurie Garden.

Stand on the corner of Michigan and Adams, marked as the starting point of Historic Route 66. Enjoy coffee and a big breakfast at Lou Mitchell’s, a Chicago institution since 1923 and a must for Route 66 travellers. 

You could then walk over to nearby Grant Park and visit the Art Institute of Chicago, one of the oldest and largest art museums in the United States, or head to the nearby Loop neighborhood and take a ride on the Chicago Architecture Foundation River Cruise. Learn about the city’s fascinating architectural history as you cruise along the Chicago River, passing by iconic skyscrapers and historic landmarks.

Later, make your way to Navy Pier, a popular entertainment destination right on Lake Michigan. You can take a ride on the Centennial Wheel for panoramic views of the city skyline and Lake Michigan, and enjoy the lakefront atmosphere.

Optional Experience – Inside Chicago Grand Tour

Join this guided tour around Chicago’s best sites ending with a visit to the Hancock Tower, one of the city’s tallest landmarks.

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This morning, pick up your rental car and prepare for an unforgettable journey along Historic Route 66.

Your first stop today will be the town of Joliet, on the outskirts of metropolitan Chicago. You can visit the Joliet Area Historical Museum to learn about the history of Route 66, view vintage cars and other memorabilia. Before you leave Joliet, stop for a sweet treat at Rich & Creamy in Joliet, a beloved ice cream stand that has been serving up delicious cones, sundaes, and shakes since the 1940s.

In Wilmington, keep an eye out for the Gemini Giant, one of the iconic Muffler Men statues that line Route 66. Then make a pit stop at the Polk-a-Dot Drive In in Braidwood, a classic diner that serves up tasty burgers, fries, and shakes in a retro setting.

As you approach Springfield, make a detour to visit the Lincoln’s Home National Historic Site, where you can tour the preserved home where Abraham Lincoln lived with his family before becoming president. Alternatively, stop in Springfield to visit the Cozy Dog Drive In, the birthplace of the ever popular corn dog.

Cross the Mississippi River on the historic Chain of Rocks Bridge, which once carried the Route 66 traffic between Illinois and Missouri. You can walk across the bridge to enjoy panoramic views of the famous river. Before reaching your hotel in St. Louis, you may like to make a final stop at Ted Drewes Frozen Custard, a beloved local institution that has been serving up delicious frozen treats since 1929.

Chicago > St. Louis | 297 miles

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We suggest starting your day at the Gateway Arch, the iconic symbol of St. Louis. Adjacent to the Gateway Arch is the Old Courthouse. You can explore the historic building and learn about the historic cases tried there. Alternatively, you can enjoy a leisurely stroll through Citygarden, an urban park in downtown St. Louis featuring sculptures, fountains, and landscaped gardens.

You can head to Laclede’s Landing for lunch. This historic district along the riverfront is known for its dining and entertainment options.

Spend the afternoon exploring Forest Park, one of the largest urban parks in the United States. Visit attractions such as the Saint Louis Art Museum, the Saint Louis Zoo, and the Missouri History Museum. After exploring Forest Park, head to The Delmar Loop, a vibrant entertainment district known for its eclectic mix of shops, restaurants, and live music venues.

Perhaps have dinner in The Hill neighborhood, known for its Italian-American cuisine, before ending your day back at the Gateway Arch, which is illuminated after dark.

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Begin your drive at the Route 66 State Park, located just outside of St. Louis. It is on the abandoned site of the town of Times Beach, a summer resort spot in the 1920s for the city dwellers of St. Louis. The visitor centre is the former Bridgehead Inn, a 1935 roadhouse that sat on the original Route 66.

You may like to make a detour to view the Meramec Caverns, one of the largest and cave systems along Route 66. You can take a guided tour of the caverns to marvel at the impressive limestone formations.

Be sure to stop in the town of Cuba, known as the “Route 66 Mural City” for its vibrant murals depicting scenes from the road’s heyday. Don’t miss the Wagon Wheel Motel and the restored Route 66 Rocker, iconic landmarks along the route.

Drive through Devil’s Elbow, a scenic stretch of Route 66 known for its winding road and picturesque views of the Big Piney River. You may like to stop at the Elbow Inn Bar & BBQ for a bite to eat and to admire the vintage decor.

Make a final stop in Marshfield, birthplace of Route 66 co-founder Edwin P. Hubble. You can visit the Hubble Birthplace State Historic Site to pay homage and learn more about Hubble’s life.

St. Louis > Springfield | 216 miles

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We think you will like to spend your morning in Springfield at the Route 66 Car Museum. The museum features a collection of classic cars and memorabilia from the heyday of America’s most famous highway.

Enjoy lunch at the Springfield Brewing Company, a popular brewery and restaurant located in downtown Springfield. If you are not driving, you can sample a variety of craft beers brewed on-site.

In the afternoon you might like visit the Discovery Centre, a hands-on science museum that offers interactive exhibits, or descend into the ‘Fantastic Caverns’, where you can ride on a guided tram tour through the caves.

Take a leisurely stroll along historic Commercial Street in the evening. You can browse the boutiques and galleries, and grab dinner at one of the local restaurants.

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Today’s drive follows Historic Route 66 through three different states; Missouri, Kansas and Oklahoma.

Continuing in Missouri you may like to stop in the historic town of Carthage. The courthouse dates back to 1894 and you can stroll through downtown to see more historic architecture and murals.

In Joplin you can discover the area’s mining heritage and the modern day fight against devastating tornados, then make a quick stop in the town of Galena to see the “Cars on the Route” attraction, featuring the famous Tow Mater truck from the Pixar movie “Cars.”

Cross over the border to briefly drive through Kansas. You can stop at the Eisler Brothers Old Riverton Store, a historic general store and gas station that dates back to the 1920s, and then visit Baxter Springs, where you can visit the Heritage Centre, to learn the town’s role in the Civil War and Route 66.

Cross the border into Oklahoma, where you can stop in the town of Miami to visit the Coleman Theatre, a historic theatre with Spanish Colonial Revival architecture.

Before you reach Tulsa, make a detour to Claremore to visit the Will Rogers Memorial Museum, dedicated to the famous cowboy. You can explore exhibits on Rogers’ life and career, see his collection of memorabilia.

Springfield > Tulsa | 195 miles

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You may like to start your day at the Philbrook Museum of Art, housed in a beautiful Italian Renaissance villa surrounded by lush gardens. You can explore the museum’s extensive collection of European, American, and Native American art, as well as take a stroll through the gardens to admire the sculptures and flowers.

You can continue this horticultural theme by heading to the Tulsa Botanic Gardens, a peaceful oasis featuring a variety of themed gardens, walking trails, and outdoor sculptures.

We recommend a leisurely lunch at one of the restaurants in the Cherry Street District, a vibrant neighborhood known for its eclectic dining scene.

Music enthusiasts will enjoy spending the afternoon exploring the Woody Guthrie Centre, dedicated to the life and legacy of the legendary folk singer and songwriter, whilst those wishing to continue the Route 66 theme will like to visit the Cyrus Avery Plaza and Route 66 Memorial Bridge. This area features sculptures, interpretive panels, and a large Route 66 shield sign.

In the evening stop by the he corner of East 11th Street and South Atlanta Avenue, where the neon Route 66 sign will be illuminated.

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Start your day by heading north of Tulsa to Woolaroc, located near Bartlesville. The Woolaroc Museum features an extensive collection of Western art, Native American artifacts, and historic firearms.

From Woolaroc, continue north to the Tallgrass Prairie Preserve near Pawhuska. This expansive nature reserve protects one of the last remaining tallgrass prairie ecosystems in the world. You can take a driving tour, along the preserve’s scenic loop road, to spot bison, deer, and other wildlife roaming freely in their natural habitat.

After exploring the Tallgrass Prairie Preserve, head into the town of Pawhuska. This historic town is known for its charming downtown area, which features boutique shops, art galleries, and restaurants.

Before heading back to Tulsa, make a stop at the Hard Rock Hotel & Casino in Catoosa. Even if you’re not a gambler, you can explore the hotel’s rock ‘n’ roll memorabilia, dine at one of the restaurants, or people-watch with a drink at the bar.

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Follow Historic Route 66 out of Tulsa and across the Arkansas River on Cyrus Avery Bridge. You may like to stop at the Route 66 Historical Village, an open air museum that focuses on the oil industry and transportation. The Visitor Centre is a replica of a 1920’s Phillips 66 gas station,

Further down the road at Sapulpa, the ‘Heart of Route 66’ car museum is noticeable for the world’s tallest gas pump! It also houses an ever-changing display of classic and historic vehicles, so worth a stop on today’s route.

Just west of the town of Bristow, you can find the historic Rock Creek Bridge, also known as the Pony Bridge. This iconic Route 66 bridge, built in 1924, is listed on the National Register of Historic Places. In the town of Chandler the Route 66 Interpretive Centre offers a unique slant on the Mother Road, with a video and art presentation.

As you approach Oklahoma City, follow Route 66 to Arcadia to visit the Round Barn. This unique structure, built using a circular design, has been restored and now serves as a museum. Another classic pit-stop Just outside of Arcadia, stop at Pops, a popular roadside gas station known for its giant soda bottle sculpture and a selection of over 700 varieties of soda!

Continue into Oklahoma City to find your downtown hotel.

Tulsa > Oklahoma City | 117 miles

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Today you have a full day to explore Oklahoma City at your leisure.

For an authentic cowboy experience head to Stockyards City, home to one of the largest cattle markets in the world. Auctions are held on Mondays and Tuesdays, but there’s plenty to see (and buy!) on other days of the week.

Also on the southern side of the Oklahoma River is the First Americans Museum, which explores the history, culture and resilience of each of the 39 tribes that call Oklahoma home.

After a stroll through the Crystal Bridge Tropical Conservatory at Myriad Botanical Gardens, head to gentrified Bricktown to wander between trendy bars, or ride the fun and informative water taxi.

In the evenings there is always live music across the city, but if you are in town on a Saturday we recommend getting yourself a ticket for the Rodeo Opry, Oklahoma’s ‘official country music show’ that features rising stars from around the state.

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As you have now reached the halfway point of Route 66, today you will begin to head south, away from Historic Route 66, and toward your destination of Dallas-Fort Worth. However, there is still plenty more to see and do on the way.

Head south-west out of Oklahoma City on Highway 44 towards Chickasha. You may like to visit the Chickasha Antique Auto Club Museum to see their collection of vintage cars and other vehicles or just take a stroll through the beautiful Shannon Springs Park.

Continue on Highway 44 to visit the Wichita Mountains Wildlife Refuge near Lawton. Whilst enjoying the scenic drive through the refuge keep your eyes peeled for the resident bison, elk and prairie dogs as well as various native birds of prey.

Drive east out of Lawton along Highway 7 to the charming town of Duncan. The town has a rich history and vibrant arts scene, so you may wish to spend the evening wandering around downtown. We recommend visiting the Chisholm Trail Heritage Centre to learn about the famous cattle trail that passed through the area. Another great place to visit is the Kochendorfer Brewing Co. located north of town and worth the trip!

Oklahoma City > Duncan | 140 miles

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Just south of Duncan, you’ll find the Chickasaw National Recreation Area, near the town of Sulphur. You may like to explore the park’s natural springs, calm lakes, and various hiking trails. You can even take a dip in the refreshing waters of Little Niagara or Veterans Lake if the weather permits.

As you approach the Dallas metropolitan area, we recommend making a brief detour to visit the Fort Worth Stockyards, a historic district that preserves the city’s cattle industry heritage. You will be able to explore the lively streets lined with Western-style shops, restaurants, and entertainment venues, and there are daily cattle drives and rodeos.

From the stockyards it is a short drive to your hotel in the historic town of Grapevine. You will find many boutique shops, galleries, wineries and restaurants in downtown Grapevine.

Duncan > Grapevine | 160 miles

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You may like to begin today by taking in the view of the surrounding area from 150-feet up in the Grapevine Observation Tower. The 360-degree views include the impressive skylines of both Dallas and Fort Worth,

Then you can visit Grapevine’s working artisan businesses, including the Holder Dane Gallery, Vetro Glassblowing Studio, the R Town and the traditional Grapevine Blacksmith. You will find their work appearing throughout downtown Grapevine during your stay.

Grapevine has embraced its western USA heritage to become a fun historic city, and whilst the likes of LegoLand and the the Aquarium are the cornerstone of the Grapevine Mills Mall, the town has managed to retain its small-town feel and character. It is a great place to explore on the last day of your Route 66 (East) holiday.

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You could choose to stay a little longer in Grapevine and explore more of Texas, alternatively make your way to Dallas-Fort Worth International airport in time to return your car, and check-in for your homeward flight.   

Grapevine > Dallas-Fort Worth Airport | 4 miles