Get Your Kicks on Route 66 - Chicago to OK City

Day 1

Day 1: Wednesday, June 18, 2025
Today’s the day you set out to travel the “Mother Road,” the “Great Diagonal Highway,” the “Main Street of America,” or what most of us know as “Route 66!” Once the automobile took its place as a pillar of the American lifestyle, and the open road, Route 66 came to symbolize freedom, optimism, and individualism. Board one of Trailways Travel’s luxury touring motorcoaches where you will be greeted by one of our friendly hosts and drivers from the available departure location of your choice. Then it is time to make our way to the very beginning of the Route in the Windy City of Chicago. Rest and refresh breaks along with a lunch stop will be made along the way.
Here we will meet with our Route 66 Travel Director who will be with us for the duration of our trip. This guide will be full of information about Route 66, what it stood for, and how it impacted America. We will take a short walk to the starting point of “The Mother Road” and there is no better way to start your Route 66 experience than at the Historic Route 66 Begin Sign. The original inception of Route 66 in 1926 placed its starting point at the intersection of Jackson Blvd and Michigan Ave. You will certainly want to get some great photos here to mark the beginning of your adventure!
Check into the Palmer House, an historic hotel located in the heart of Chicago. Did you know that the Palmer House was an extravagant wedding gift from Potter Palmer to his wife Bertha? And, did you know that only 13 days after its grand opening it fell victim to the Great Fire of Chicago? It was rebuilt and housed its first guests in November of 1873 making it now the nation’s longest continuously running hotel. It is now known as the Palmer House, a Hilton Hotel.
Freshen up for this evening’s dinner – traditional Chicago-style deep dish pizza. Then finish the day with a wonderful Evening Architecture River Cruise. Serene and bathed in a softer light, the city’s architecture takes on a whole new life as it begins its transition from day to night. We return back to our hotel for a great night of rest before heading out to get our “Kicks on Route 66” in the morning.

Day 2

Day 2: Thursday, June 19, 2025
We begin our day in the true iconic spirit of the Route with a breakfast at Lou Mitchell’s, which has been dubbed as the “first stop on the Mother Road.” Here you will enjoy a classic American diner experience, complete with fluffy pancakes, Belgian waffles, and shakes – not to mention what the neon sign proclaims as “the worlds’ finest coffee.” After breakfast we will board the motorcoach and set out departing Chicago and beginning our journey down the old road driving on Route 66 whenever possible. Route 66 was decommissioned in 1985 and it is said that the Federal Interstate Act of 1956 is what doomed the two-laned beloved highway by either chopping it up, rebuilding portions of it, or leaving sections to languish.
We will stop for lunch, on your own, in Pontiac, IL, home to the Route 66 Association of Illinois’ Hall of Fame and Museum. Pontiac also houses twenty-five large murals with themes from Pontiac’s economic, social, and political past - featuring the world’s largest Route 66 shield.
Continuing on our way, we will make a stop in Towanda, a community of 500 people located a little more than 100 miles southwest of Chicago on Old Route 66, and Normal. In 1977, a 3.5 mile section of Route 66 was abandoned and closed off to motorized traffic. Beginning in 1998, students and faculty of Normal Community High School, Illinois State University, and members of the local community began to convert this portion of road into a linear park. Benches, split-rail fencing, sidewalks, Burma Shave signs, flagpoles, bridges, and entryway signs have been added since 1998. A large outline map of the United States was painted on the roadbed showing Route 66 from Chicago, Illinois to Santa Monica, California. This is the only interactive map you will find along the entire stretch of Route 66. This exhibit originated as a class project for Normal Community High School geography and history students.
As we make our way further down the route, we stop to visit the Abraham Lincoln Presidential Library & Museum in Springfield, IL. Documenting the life of our 16th U.S. President the museum combines historical artifacts with cutting-edge exhibits, life-sized dioramas, and multimedia presentations to tell Lincoln’s story from his early years through his presidency and the Civil War. Highlights include the “Journey I” and “Journey II” exhibits, which showcase key moments in Lincoln’s life, as well as a replica of the White House during his administration.
Tonight we will be staying at the Drury Inn & Suites Springfield. After checking in with some time to freshen up and perhaps partake in a drink or two during the Kickback Reception, we venture out for a fun dinner this evening. You will find that Motorheads Route 66 Bar & Grill is a unique dining destination that celebrates the iconic Mother Road. Featuring a lively atmosphere with classic car and motorcycle memorabilia, paying tribute to the rich history of America’s most famous highway we thought this is the perfect place to end the day. The menu offers a variety of American comfort food, including burgers, sandwiches, and BBQ, making it a popular spot for both locals and travelers. It also showcases an impressive collection of vintage automobiles, offering visitors a nostalgic journey through automotive history, with exhibits that celebrate the golden age of classic cars and Route 66 and a store full of everything Route 66.

Day 3

Day 3: Friday, June 20, 2025
Rise and shine, it’s time for a great Drury Inn hot breakfast buffet before we check out and make our way for more adventures today. Route 66 across Missouri stretched 317 miles and connected a variety of large cities and small towns, traversing rolling hills and valleys. We hit the road and make our way to St. Louis, MO to visit an iconic Route 66 stop – the Gateway Arch. This 630-foot monument symbolizes the westward expansion of the United States. As the tallest man-made structure in the Western Hemisphere, it offers stunning views of the Mississippi River and the city skyline, having made it a must-see attraction for those in the hey-day of traveling the Mother Road and still for those today. The Arch underwent a major renovation completed in 2018, which revitalized the surrounding park, improved accessibility, and expanded the museum beneath it. Included today is the tram ride, a unique experience that takes you on a 4-minute journey inside the iconic structure. The tram’s cozy, pod-like cabins ascend to the observation deck, where you’ll be rewarded with breathtaking panoramic views of St. Louis, the Mississippi River, and beyond. After having a lunch on your own we continue west on the Old Road to another iconic stop, Meramec Caverns. Beneath the fertile rolling hills of the Meramec Valley, lies a complex of mineral formations and color as rare and unique as they are beautiful. Participate in a guided tour of these amazing caverns before departing for Cuba, MO, also known as “Route 66 Mural City” as designated by the Missouri legislature in 2002. Here you will find 14 outdoor murals that depict scenes from local and national history, including visits from Harry S. Truman, Amelia Earhart, and Bette Davis. Each mural has a unique story. As we continue along the Route 66 Corridor, we will explore more sights including the world-famous Route 66 Giant Rocking Chair and the Giant Faucet. Between Lebanon and our arrival in Springfield is the Route 66 Welcome Center at the Conway Rest Area featuring a nice, short walking trail and lots of Route 66 references. As we make our way into Springfield we will visit the Museum on the Square with one of the largest Route 66 timelines and maps in the country. From neon signs to classic cars to drive-ins, Route 66 represents a time in American history that captivates nostalgia lovers everywhere. Hop into the turquoise blue ‘57 Chevy Bel Air convertible at the John T. Woodruff Theater and learn about the Springfieldian who helped give Route 66 its name. After that, enjoy your stroll through numerous interactive neon sign exhibits and take photos of your favorite spots along the historic Mother Road. We’ve one more stop just a couple minutes away at the Route 66 Visitor Center where you can pick up maps and more plus have lots of information about the Mother Road at your fingertips.
We end our day at the Drury Inn & Suites Springfield (MO). An included group dinner will be at a local favorite restaurant this evening.

Day 4

Day 4: Saturday, June 21, 2025
Take in another great Drury Inn hot breakfast buffet today before we depart and make our way into the state of Oklahoma following the route through Kansas. Situated between Springfield and Joplin is Carthage, MO. One of the first concrete-paved portions of Missouri’s highway system was the stretch of road west of Carthage to Joplin, laid in 1920. In 1926, this route became part of Route 66. Along the route today travelers find Kellogg Lake, Powers Museum, Carthage Municipal Park, Stone’s Throw Dinner Theatre, 66 Drive-In Theatre and the 1939 Boots Court. It is also home to a reproduction of the Gay Parita Sinclair Filling Station. We make our way into Kansas with a picture stop at Cars on the Route in Galena. Here we meet the characters from the 2006 animated movie Cars (Lightning McQueen, Tow Mater, Luigi, and more) scattered on Kansas’s 12.8-mile portion of Route 66. It’ll be a fun photo opportunity with these famous Cars characters!
We find ourselves soon crossing over into the state of Oklahoma where we arrive in Miami, OK (pronounced my-am-uh, not my-am-ee) with a visit. tour and lunch at the historic Coleman Theater. Miami, Oklahoma, may be a small town, but the Coleman Theatre stands as a testament to its rich cultural heritage and is a true gem of historic Route 66. Built in 1929, this opulent theater was a gift to the community from George L. Coleman Sr., a local mining magnate. Inside, the theater is a visual feast, with its ornate ceilings, intricate moldings, and the stunning Mighty Wurlitzer pipe organ that still fills the hall with music today.
As we continue on down the Route, we come to Ed Gallaway’s Totem Pole Park. For those traveling Route 66, Totem Pole Park offers a delightful detour—a chance to explore a piece of roadside Americana that’s as fascinating as it is unexpected. The park stands as a symbol of the creativity and individuality that have long defined the spirit of Route 66, making it a must-see stop for anyone journeying down this iconic highway. You’ll find it nestled near Foyil, and it is one of the most quirky and colorful attractions along historic Route 66. Created by the skilled craftsman and folk artist Ed Galloway in the mid-20th century, the park is home to the world’s largest concrete totem pole, standing an impressive 90 feet tall.
On down the road we find the Blue Whale of Catoosa, another of Route 66’s beloved and whimsical roadside attractions. Located just outside of Tulsa, this bright blue behemoth has been delighting travelers since the early 1970s. Built by Hugh Davis as a surprise anniversary gift for his wife, Zelta, the Blue Whale quickly became a favorite stop along the route.
In Tulsa, we check in to the Hampton Inn & Suites Tulsa Downtown for a two-night stay. In Tulsa, the AAA Route 66 Road Fest is going on celebrating America’s most iconic highway. Held annually, this festival brings together car enthusiasts, history buffs, and travelers of all ages to honor the legacy of Route 66. At the Road Fest, classic car shows are a highlight, with rows of beautifully restored vintage vehicles that harken back to the golden age of road trips. You can wander through exhibits showcasing Route 66 memorabilia, historical displays, and art inspired by the highway’s storied past. For those interested in the history and culture of Route 66, the festival offers fascinating presentations, film screenings, and panel discussions featuring historians, authors, and Route 66 enthusiasts. Since food and drinks are also a big part of the experience, we will have our dinner here, on your own. The festival features a wide range of food trucks and vendors offering everything from classic American diner fare to more modern, gourmet treats. Local craft beers and Route 66-themed cocktails add to the festive atmosphere.
Live music is another key attraction, with bands playing everything from rock ‘n’ roll and country to blues, ensuring there’s a tune for everyone to enjoy. For those looking to take a piece of the festival home, the vendor booths offer a variety of Route 66-themed souvenirs, from T-shirts and artwork to books and handcrafted goods. You’ll soon find that it is more than just a festival; it’s an immersive journey through time that celebrates the enduring allure of Route 66 and its place in American culture!

Day 5

Day 5: Sunday, June 22, 2025
Enjoy a leisurely morning with breakfast at the hotel before we depart for a short drive to Claremore for a tour of the Will Rogers Memorial Museum. You will find that it is more than just a collection of artifacts; it’s a celebration of a man whose humor, humility, and love for people continue to resonate today. For many, it’s a chance to reminisce, learn, and be inspired by the timeless wisdom of Will Rogers in a setting that is both peaceful and deeply connected to the history and culture of Oklahoma. The museum is housed in a beautiful stone building surrounded by well-manicured gardens and scenic views. Inside, you can explore extensive exhibits that showcase Will Rogers’ life, from his early days as a cowboy to his rise as a film star, radio personality, and newspaper columnist. The museum features a collection of artifacts, photographs, film clips, and personal memorabilia, providing a comprehensive look at the man who became known as the “Oklahoma’s Favorite Son.”
We return back to Tulsa with the rest of the day free to enjoy the AAA Route 66 Road Fest. We will provide a shuttle service between the hotel and the festival at specific times during the day. Lunch and dinner will be on your own while at the festival. Upon arrival back to the hotel, enjoy the evening before we depart in the morning to continue our Route 66 journey.

Day 6

Day 6: Monday, June 23, 2025
Enjoy a last leisurely breakfast morning at the hotel before checking out and departing for more historic Route 66 explorations. Our first stop today will be in Chandler, at the Route 66 Interpretive Center. Housed in a historic armory building, this center immerses visitors in the history of Route 66 through interactive exhibits, vintage photos, and nostalgic artifacts. It also offers a visually entertaining and immersive “drive” experience that transports you back to the heyday of America’s most famous highway. This unique feature allows you to settle into classic car seats while watching a panoramic video that simulates a road trip along Route 66. As the scenes unfold, you’ll journey through different eras, landscapes, and iconic stops along the Mother Road, all accompanied by the sights and sounds that once filled the highway. The “drive” brings the spirit of Route 66 to life in a fun and engaging way, making it a highlight of any visit to the center. It’s a nostalgic nod to the golden age of road trips, where every mile was an adventure, and the open road promised new discoveries around every bend.
As we continue on our way, we find a place that takes a delightful step back in time at the Arcadia Round Barn. This iconic, century-old structure, with its unique circular design, stands proudly along the highway in Arcadia, Oklahoma. Inside, the barn features fascinating displays of local history and Route 66 memorabilia, offering a glimpse into the region’s past. The barn’s loft, with its beautifully restored woodwork, often hosts live music and community events, making it a lively stop for travelers.
We travel just a bit down the road to POPS, a must-visit stop for any Route 66 tour, combining modern flair with nostalgic charm. Known for its towering 66-foot-tall soda bottle sculpture, which lights up in vibrant colors at night, POPS is a beacon for travelers on the Mother Road. Inside, the sleek, glass-fronted building houses over 700 varieties of soda, from classic colas to unique and quirky flavors from around the world. As we will be having lunch here today, on your own, be sure to grab a burger at the retro-style diner that offers up a classic drive-in menu and relax with a cold drink while soaking in the scenic views. The combination of its eye-catching design, the fun of picking out new sodas, and the connection to the iconic highway makes it a memorable stop on our journey. It really is a place where the old and new collide in the most refreshing way!
From here we continue on to Oklahoma City with a stop to tour the First Americans Museum. This cultural landmark honors the diverse histories, cultures, and contributions of the 39 Native American nations in Oklahoma. It was formerly known as the American Indian Cultural Center and Museum, went through a renovation and officially opened on September 18, 2021as the FAM. Only a few tribal Nations were indigenous to what is now the State of Oklahoma. All others were removed from homelands across the contiguous U.S. to Indian Territory. In 1907 Oklahoma became the 46th state to enter the union. The State of Oklahoma’s name comes from two Choctaw words Okla and Homma. Translated it means “Red People,” the place they now call home.
We check into the Hampton Inn & Suites Oklahoma City – Bricktown for our overnight stay. With its great location and easy access to restaurants and things to do, the evening is yours to explore as you wish with dinner on your own.

Day 7

Day 7: Tuesday, June 24 2025
Good morning, it’s time for a good breakfast at the hotel before checking out and departing for the day. Today is the day that we begin our journey back home, but we have more to see and do along the way. As we bid farewell to Oklahoma City, our first destination is home to Ree Drummond, the Pioneer Woman who many of you know from the Food Network. Pawhuska, Oklahoma became extremely popular once she gained such notoriety. But Pawhuska is also known for the Osage Tribe. The recent movie, Killers of the Flower Moon was filmed here and tells the harrowing true story of the Osage Nation murders in the 1920s. The film, based on David Grann’s bestselling book, delves into the dark history of greed and exploitation that surrounded the oil-rich Osage people, leading to a series of brutal crimes. Pawhuska, with its authentic setting, played a crucial role in bringing this gripping and tragic chapter of American history to life on screen. At one time, the Osage people were among the wealthiest in the nation. The Osage peak oil production and income were reached in 1923 when more than 40 million barrels were produced. That year, the Osage tribal members collectively received royalties and bonuses amounting to more than $400 million in today’s value. You will learn more about this tribe’s history as we visit the Osage Nation Museum. Then we take a visit to the Pioneer Woman Mercantile for some home décor ideas, gifts, kitchenware, Ree’s cookbooks, treats and more. The on-site deli and bakery serve up comfort food favorites, from hearty sandwiches to mouthwatering pastries, making it a perfect spot for lunch during our visit to this charming small town. Take time to browse the many other shops and places for lunch, on your own, as well.
We depart for a short drive to Bartlesville and the Woolaroc Museum and Wildlife Preserve. Established by oilman Frank Phillips in the 1920s, Woolaroc spans 3,700 acres of pristine landscape, home to a diverse range of wildlife, including bison, elk, and longhorn cattle. Here you can explore the museum, which houses an impressive collection of Western art, Native American artifacts, and historical exhibits that tell the story of the American West. You will see why Will Rogers called it “the most unique place in the country.”
As we continue our journey down the highway, we end our day in Kansas City where we will check into the Hampton Inn Kansas City/Liberty. And you just know we can’t be in KC and not have a farewell KC BBQ dinner at one of the local favorites.

Day 8

Day 8: Wednesday, June 25, 2025
Have breakfast this morning before making our return back home today. We bid farewell to our local tour director that has been with us and set off. We will make our usual rest and refresh breaks and meal stops as needed. We hope that you have made some very fond memories of your time traveling the famed Route 66, the Mother Road, the Diagonal Highway with us! It certainly did span the heart of America symbolizing mobility from the impact of the automobile, freedom and the pursuit of the American Dream.