Route 66 ~ 100th Anniversary

Route 66 Centennial Odyssey: Chicago to Oklahoma City

2026
11 Days / 10 Nights

Custom-tailored for Your Group

Celebrate the 100th Anniversary of America's most iconic road trip with our Route 66 Centennial Odyssey: Chicago to Oklahoma City! This 11-day adventure takes you through the heart of the Mother Road, starting in Chicago and winding through legendary Route 66 landmarks.
You'll explore bustling cities, historic small towns, quirky roadside attractions, and hidden gems along the way. From Chicago’s architectural wonders to the art deco beauty of Tulsa and the cowboy spirit of Oklahoma City, this trip is packed with history, culture, and unforgettable experiences. Join us for the ultimate nostalgic journey on Route 66!

Duration
11 Days /10 Nights

Group size
Min 35

Customization
Available!

This itinerary offers a blend of history, quirky Route 66 landmarks, and local culture, perfect for a nostalgic road trip experience.

 

Highlights Include:

  • Guided Chicago City Tour
  • Joliet's Old Prison
  • Route 66 Hall of Fame & Museum
  • Guided Springfield City Tour
  • Abraham Lincoln Presidential Library and Museum
  • Chain of Rocks Bridge in St. Louis
  • Jefferson National Expansion Memorial ("The Arch")
  • St. Louis Old Courthouse
  • Soldiers Memorial Military Museum
  • National Museum of Transportation
  • Eureka Route 66 State Park
  • Meramec Caverns
  • Jesse James Wax Museum
  • The Wagon Wheel Motel
  • Missouri University of Science & Technology
  • Devil's Elbow
  • U.S. Army Engineer Museum at Fort Leonard Wood
  • Route 66 Neon Park
  • The Munger Moss
  • Laclede County Library & Route 66 Museum
  • Edwin Hubble Hometown Tour
  • "Queen City" or "Birthplace of the Mother Road" Guided Tour
  • History Museum on the Square
  • Route 66 Car Museum
  • Fantastic Caverns Drive-Through Cave
  • Gay Parita
  • Red Oak II
  • Carthage Driving Tour
  • Guided Joplin City Tour
  • Cherokee Nation Anna Mitchell Cultural Center
  • Blue Whale of Catoosa
  • Guided Tulsa City Tour
  • Philbrook Museum
  • Bristow History Museum
  • Rock Café
  • Route 66 Interpretive Center
  • McJerry's Route 66 Gallery
  • Seaba Station
  • Oklahoma City Touring
  • National Cowboy & Western Heritage Museum
  • Oklahoma State Capitol Building
  • Oklahoma City National Memorial
  • Skydance Pedestrian Bridge
  • The Centennial Land Run Monument
  • American Banjo Museum
  • Bricktown City Touring by land & by water

Sample Itinerary ~

 
Day 1 -
  • Start your adventure in Chicago, IL. Explore iconic landmarks with a Step-on Guide and enjoy Instagram-worth photo opportunities next to the Chicago “bean”, Buckingham Fountain, cruising along Jackson Blvd., or admiring the view from the Navy Pier.
  • Grab an iconic Chicago Dog or slice of deep-dish pizza. Visit historic Shedd Aquarium. See the city from the water on an architecture boat tour.
 
Day 2 -
  • Enjoy breakfast at your hotel this morning prior to checking out.
  • Time to “get your kicks” and start to follow the pathway of Route 66. Stop in Joliet for a photo op with Jake and Elwood in front of the Historical Museum, then tour the Old Joliet Prison that was in use from 1858 – 2002.
  • Stop for ice cream at Rich and Creamy before heading on toward Springfield IL. All along the route watch for giant “muffler men”, murals and nostalgic gas stations.
  • Swing through Wilmington for a photo of the Gemini Giant. This enduring icon is the Gemini Giant, a towering 28-foot-tall statue that, along with The Launching Pad restaurant it stood watch over since 1965, was inducted into the Route 66 Hall of Fame of Illinois in 2000. The Giant now stands in the City’s South Island Park.
  • A little further down the road is the village of Dwight, home of Amblers Texaco, also known as Vernon’s Texaco Station and Becker’s Marathon Gas Station. The station gets its name from longtime manager Basil “Tubby” Ambler, who operated the station from 1938 to 1966. It also serves as the town’s visitor center.
  • Stop for a break in Pontiac. Then, take in The Route 66 Hall of Fame and Museum. Located in the heart of downtown Pontiac, the museum is housed in the historic Pontiac City Hall building, which was constructed in 1891.
  • Just past Bloomington is the Hamlet of Funks Grove- make a quick stop at Funks Grove Pure Maple Sirup Farm and shop- an unexpected souvenir of the route!
  • Rest your head tonight in Springfield, IL.
 
Day 3 -
  • Enjoy breakfast at your hotel this morning prior to checking out.
  • Springfield- the capital of Illinois and home to Abraham Lincoln for many years. Visit the Presidential Library and Museum, embark on a docent-led tour of his tomb, and see the only home he ever owned.
  • Some additional classic Rt 66 sites to keep watch for are the Cozy Dog Drive-in and Shea’s Gas Station Museum. There is also a giant Abe Lincoln statue-“Axe murderer Abe” is the nickname. If you stop by the fairgrounds to see him you will see why he earned this moniker.
  • As you head south from Springfield there are plenty of photo ops: drive through Lauterbach home of another Muffler Man, Chatham, IL, has a 1.4-mile-long piece of restored hand-laid brick road - a segment of 66 done in 1931 and placed over a concrete roadbed, and Carlinville’s largest single collection of Sears kit homes in the United States - just to name a few.
  • Before you arrive in St Louis, make a stop at the Chain of Rocks Bridge. Because the bridge has not been significantly altered over the years, a visit there today conveys a strong sense of time and place, an appreciation for early-20th-century bridge construction, and outstanding views of the wide Mississippi River. The Chain of Rocks Bridge was listed in the National Register of Historic Places in 2006.
  • Enjoy dinner this evening and check-in to your local MARS Partner-property for the night to rest and relax.
 
 
Day 4 -
  • Fill up with breakfast at the hotel this morning before hitting the road!
  • Explore the wonderful river city of St Louis, MO. From your hotel it is an easy trek to The Jefferson National Expansion Memorial-more commonly known as the Arch. The unofficial symbol of the city, it houses the museum of Westward expansion, an “elevator” to the top of the 630 foot landmark, and offers incredible views of the Old Courthouse, the city, and the Mighty Mississippi.
  • Don’t miss a visit to the Old Courthouse- the site where the famous Dred Scott Decision was rendered.
  • Stop at the Soldiers Memorial Military Museum and the National Museum of Transprotation. Don’t forget to grab some Custard at the Original Ted Drewes on Chippewa!
  • Return to the hotel to rest for the evening.
 
 
Day 5 -
  • Enjoy an included breakfast at the hotel this morning prior to checking out.
  • Time to continue across Missouri. Stop at Route 66 State Park in Eureka. Located just outside St. Louis, this park preserves the history of Route 66 in Missouri. It features a visitor center with exhibits on the highway's history and a section of the original road.
  • Stop in Stanton to explore Missouri’s largest commercial cave, Meramec Caverns, with an easy guided walking tour.
  • Don’t miss the original sign for the Jesse James wax museum! The water tower soaring above the town of Bourbon is a whimsical photo stop before coming into Cuba, the city of Murals. Cuba is also home to the oldest continuously operating Motel on Rt 66- The Wagon Wheel Motel.
  • You may choose to have lunch in town or continue a little farther to St James. Sample wines from one of the many muscadine vineyards in the area.
  • Make your next stop in Rolla, MO, home of Missouri University of Science and Technology- a premier engineering school. On campus you can find an actual nuclear reactor and a half scale replica of Stonehenge!
  • Before you arrive in St Robert, venture onto an original portion of the route that will take you back to Devil’s Elbow. This bend in the Piney River cuts through the Hiawatha Bluffs and affords stunning scenery.
  • For those with a quirky sense of humor, stop at Uranus Town center, before venturing to The U.S. Army Engineer Museum at Ft Leonard Wood. This federal museum, chartered through the United States Army, offers a variety of gallery displays including: the development of American Army engineering equipment, topographic engineering, landmine warfare, tactical bridging, special weapons, and much more.
  • Come in to St Robert for the night and an evening visit to the brand new Route 66 Neon Park at the George M Reed Roadside Park. The park features restored, orphaned Route 66 neon signs in an outdoor park-like setting with corresponding story boards to inform the public about the history of each sign.
 
Day 6 -
  • Enjoy breakfast at your hotel this morning prior to checking out.
  • Lebanon is a town with several photo ops of motels and motor courts from a bygone era. The Munger Moss is still family operated and has a quaint gift shop.
  • Stop into the Laclede Couty Library to visit the Route 66 museum. Take a guided tour of this museum, which features recreations of a 1950s gas station and a classic diner, along with displays of antique cars, a collection of Route 66 books, magazines, and videos. You can also stop at Shepherd Hills Factory Outlets- featuring shops and wares more suited to the Ozarks, and the ever popular, Ozarks made, Walnut Bowls.
  • Just down the road is the town of Marshfield, the hometown of Edwin Hubble. Hubble became one of the most famous astronomers of the 20th century, contributing to our understanding of the expansion of the universe and leading to our knowledge of the Big Bang. There is a 1200 pound, one quarter sized replica of the Hubble Space Telescope in the town square.
  • While not a remnant of Route 66 no great road trip is complete without a stop at Buc-ees! This Texas based Mega store and gas station is a staple in the southern states, and this location just outside of Strafford is Missouri’s first. If you haven’t been to Buc-ees, you haven’t been on a road trip!
  • Since shopping in megas stores seems to be the theme- make one more stop at Bass Pro Shop in Springfield. This store is the “Granddady of them all”. This is the original Bass Pro, and now is the largest as far as retail space. It is also home to The National NRA museum and Wonders of Wildlife Aquarium and Museum.
  • Check-in to your local MARS-partner property location for some classic R&R.
 
 
Day 7 -
  • Fill up with breakfast at the hotel this morning before hitting the road!
  • Take time to explore the “Queen City” or the “Birthplace of the Mother Road”.
  • Learn how the idea of Rt 66 first came to be in Springfield, MO as you visit the History Museum on the Square. You can also see the spot where Wild bill Hickock was shot! Art deco buildings and theaters surround the square as well as the very unique Abu Ben Adhem Shrine Mosque.
  • Visit the Route 66 Car Museum, have a burger at Reds Hamburg and ride a tram through the world’s only drive through cave- Fantastic Caverns.
  • Venture south and enjoy dinner at the Ozark Mill- a beautifully restored mill over looking the Finley River.
 
 
Day 8 -
  • Enjoy an included breakfast at the hotel this morning prior to checking out.
  • Take the road less traveled when leaving Springfield this morning. The original 66 is now 266 as it heads west through farmland and small towns. 30-minutes into the drive you will come upon Gay Parita. Recreation of a 1930 Sinclair gas station, taking you for a journey in time. The site includes a replica station, along with original pumps and other memorabilia from the heyday of Route 66: The Mother Road. This is not just a replica; it's a living museum that allows visitors to immerse themselves in the past.
  • From Gary Turner’s labor of love, your next stop is the brainchild of artist Lowell Davis, who grew up in the “real” Red Oak, Missouri, about 18 miles northwest of the “new” Red Oak II. After Davis had left Red Oak for several years, he returned in the 1970s to find his hometown had become a ghost town. In 1987 he began to buy homes and businesses from the original townsite and other rural ghost towns, painstakingly moving them to this new site and restoring them to their original “grandeur.” Frozen in time, a walk through Red Oak II is a vivid stroll through the past.
  • Next is Carthage, cruise past the Boots Motel and head toward the impressive Jasper County courthouse looming over the town square. You can drive through the town’s four historic districts listed on the National Register of Historic Places. One of those is the large residential district south of the Courthouse Square, which grew as bankers, mine owners, lawyers, doctors, and merchants flocked to the City of Carthage.
  • Head down to Joplin for lunch at the Red onion Café. Then spend the afternoon with a Step-on Guide who will take you to the "must-see" spots, such as: City Hall and the Route 66 Mural Park, Grand Falls, the Bonnie and Clyde hideout, the Mineral Museum and the Candy House Gourmet.
  • Once you leave Joplin you can travel along 13 miles of the Mother Road through Kansas. Pass through Galena and curve down toward Baxter Springs, before you know it you have crossed in to Oklahoma. Oklahoma touts having the longest stretch of Route 66- about 383 miles. Pass through Quawpaw and Micky Mantle’s hometown of Commerce, before entering the town of Miami. As you go through town on Main St look for the neon sign for Waylon’s KuKu, and the lovely, restored Coleman Theater.
  • Continue on -albeit now on the interstate to the Tulsa Suburb of Catoosa. If time allows take a break at the Cherokee Nation Anna Mitchell Cultural Center. This is a place to enjoy Cherokee art, culture, and history. The two-story, 9,400-square-foot building sits on eight acres and includes a gift shop, café, and exhibit gallery. The next photo opportunity is the quirky Blue Whale of Catoosa, one of the most recognizable attractions along old Route 66.
  • Check-in to one of the many hotels in Catoosa- maybe even try your luck at the Hard Rock Casino tonight.
 
 
   
 
Day 9 -
  • Enjoy breakfast at your hotel this morning.
  • Spend the day in Tulsa with a local Guide. Explore Tulsa's rich Art Deco architecture with buildings like the Boston Avenue Methodist Church and the Philcade Building.
  • View the Golden Driller, an iconic statue that is a Tulsa landmark representing the city's oil history.
  • Visit both the Cyrus Avery Plaza, named after the "Father of Route 66," which features a giant sculpture titled "East Meets West," depicting the meeting of an old-fashioned car and a horse-drawn carriage and the Center of the universe, made famous in the Paramount + program “Tulsa Kings”.
  • Have lunch at the Mother Road Market and Visit the Route 66 Historical Village.
  • Finish the day at the gorgeous Philbrook Museum before returning to your hotel.
 
 
Day 10 -
  • Fill up with breakfast at the hotel this morning before checking out and hitting the road!
  • Head west out of Tulsa. Venture off the highway at Bristow and join the original route. Look for the restored art deco buildings that housed the Bristow Motor Company and Bristow Body Shop. The Bristow History museum is in the old railroad depot, and you can swing by the Wake Island WWII memorial.
  • Stay on the original route which will take you through Stroud, OK. Home of the famed Rock Café, a historic diner that has been serving Route 66 travelers since 1939. It's famous for its connection to the movie "Cars."
  • Continue to The Chandler Armory building in Chandler, Oklahoma; an Art Deco military building which now houses the Route 66 Interpretive Center, a museum devoted to understanding the construction and history of U.S. Route 66. Chandler is also home to McJerry's Route 66 Gallery. Jerry McClanahan is an artist and premier expert on all things Route 66. His gallery is open by appointment as he lives just minutes away. Jerry is also the author of the world acclaimed guidebook for Route 66 (EZ66) and he is happy to sign it for you if you have a copy!
  • A few miles down the road is The Seaba Station, formerly known as Seaba’s Filling Station and Seaba Engine Rebuilding and Machine Shop, built in 1921. It now contains an awesome collection of vintage motorcycles from many manufacturers. Also check out the rare outhouse in the back. One of the first outhouses that had plumbing!
  • As you're closing in on Oklahoma City, stop in Arcadia at the only round barn on Route 66. It was built by local farmer William Harrison Odor in 1898 using native bur oak boards soaked while green and forced into the curves needed for the walls and roof rafters.
  • Head into Oklahoma City and your Bricktown hotel for the night.
 
 
Day 11 -
  • Enjoy an included breakfast at the hotel this morning prior to checking out.
  • Take a break from Route 66 and soak in the history and culture of the great state of Oklahoma. This morning, visit the National Cowboy & Western Heritage Museum. With more than 28,000 Western and American Indian artworks and artifacts and the world's most extensive collection of American rodeo relics, this is America's premier institution of Western history, art and culture.
  • Embark on a tour of the Capitol Building- the only capital in the world surrounded by working oil wells.
  • Afterwards, visit the Oklahoma City National Memorial, a site honoring the victims, survivors, rescuers, and all who were affected by the Oklahoma City bombing on April 19, 1995.
  • Return downtown and take a walk across the Skydance Pedestrian Bridge-part bridge, part art-Inspired by Oklahoma’s state bird, the scissor-tailed flycatcher, Skydance bridge soars over Interstate 40. The bridge is a 380-foot-long pedestrian bridge with a 197-foot-tall sculpture.
  • Another impressive art installation awaits at the next stop, The Centennial Land Run Monument. This commemorates the opening of the Unassigned Land in Oklahoma Territory with the Land Run of 1889. It is one of the world’s largest bronze sculptures featuring 45 heroic figures of land run participants, frozen in motion as they race to claim new homesteads.
  • Back in the heart of Bricktown have fun at the American Banjo Museum. The museum's exhibits document the rise of the banjo from its arrival in North America via the Atlantic slave trade to modern times. See the Banjo Hall of Fame who’s members include Earl Scruggs, Roy Clark and Steve Martin.
  • Enjoy the water taxi’s restaurants and entertainment in Bricktown before departing for home - or plan to stay one additional night to enjoy the local nightlife.
 
 
   
 

 

 
 

 
 
 Includes: 4 nights' accommodation, 4 breakfasts, 4 dinners including the Special Patriotic Celebration Event, Full-time licensed DC Tour Guide and Logistics Manager/Tour Director, admission as stated in the itinerary, taxes, fees, and gratuity, except gratuity for driver and guide service is not included unless requested.  Call for your custom quote and start creating your dream package today!

 


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