You’ll love this tour if... you’ve always dreamed of reliving the golden age of American road trips—cruising Route 66 from Chicago to Albuquerque with classic diners, quirky roadside icons, historic landmarks, and unforgettable small-town charm along the way.

Hotel Accommodations

Nights 1 - Nickerbocker Hotel, Chicago
Night 2 - Crowe Plaza Hotel, Springfield
Night 3 - Fairfield Inn, St. Louis
Nights 4 - Home2 Suites, Joplin
Night 5 - Hampton Inn Bricktown, OKC
Nights 6 - Hyatt Place, Amarillo
Night 7 - Home2 Suites, Albuquerque
Night 8 - Element, Lone Tree (Denver)
*Subject to change

Day 1 – Welcome Dinner
Step back in time as you begin your adventure along the legendary “Mother Road,” Route 66—traveling the first half from Chicago to Albuquerque! (Stay tuned for Part Two in 2026, continuing on to Los Angeles.) Today, travel by coach to Chicago, where the famous route begins. This evening, gather with your fellow travelers for a fabulous Welcome Dinner at a classic restaurant that was a Route 66 favorite in its heyday—and still is today. Tomorrow, the journey truly begins as you get your kicks on Route 66! (D)

Day 2 – Route 66 Kickoff: Gas Stations, History & Lincoln’s Legacy
Route 66 is alive with the flavor of “Real America”—friendly people, mom-and-pop diners, neon signs, vintage motels, and roadside treasures. This morning, begin at 99 E Adams Street in Chicago, where the iconic “Begin Route 66” sign marks the start of your adventure. Travel along original alignments of the Mother Road, stopping at classic landmarks like the restored Amaco Texaco gas station and the Route 66 Hall of Fame. Continue on to the elegant Davis Mansion before arriving in Springfield, where you may visit the Lincoln Presidential Library or explore more of the town’s Route 66 gems. Dinner is on your own this evening, but don’t miss the chance to join the group for a stop at the legendary Cozy Dog Drive-In—home of the original corn dog and a Route 66 favorite! (B)

Day 3 – Roadside Icons & St. Louis Flavors
Hit the road for a day filled with quirky Route 66 charm! Depart Springfield and make your way toward St. Louis, starting with a stop at the world’s largest ketchup bottle—a 170-foot water tower built in 1949 by the Brooks brothers, inventors of the famous sauce. Continue to the Dixie Family Restaurant, America’s oldest truck stop, known for hearty, homemade meals. At Motorheads, explore classic cars and racing memorabilia before moving on to the Litchfield Museum and Route 66 Welcome Center, a must-see for travelers on the Mother Road. Tonight, arrive in St. Louis for a group dinner, capped off with a sweet tradition at Ted Drewes—the legendary frozen custard stop that has delighted Route 66 travelers for generations. (B, D)

Day 4 – Caverns, Roadside Quirks & a Drive-In Classic
Today the Mother Road carries you from St. Louis through the rolling Ozarks, where small towns and roadside icons bring Route 66 nostalgia to life. Along the way, stop for a photo with the “Hillbilly” statue at the Mule Trading Post and marvel at the world’s (second) largest rocking chair. Then, descend underground at the famous Meramec Caverns, where rare mineral formations create one of the most extraordinary cave systems in the world. This afternoon, step back into the golden age of Americana at the historic 66 Drive-In Theater, in operation since 1949. Tonight, settle into Joplin, Missouri, and enjoy an evening exploring this lively Route 66 town. (B, L)

Day 5 – Old Stores, Soda Pops & Classic Cars
Step into nostalgia this morning at the Riverton Nelson Old Store, the longest continuously operating store in the country. Stocked with groceries, flowers, Route 66 memorabilia, and an old-time deli famous for its sandwiches, it’s a true slice of yesterday. Continue your journey through charming roadside stops before arriving in Oklahoma City, where you’ll enjoy a quick visit to the OKC Mustang Car Show and a stop at the colorful Pops Soda Shop, with its rainbow wall of glass soda bottles. Tonight, check into your hotel in lively Bricktown, where dinner with the group is followed by free time to explore this vibrant district’s nightlife. (B, D)

Day 6 – Museums, Quirks & a Texas-Sized Dinner
This morning, journey west to the famous Route 66 Museum, where a guide will bring the history of America’s “Mother Road” to life through fascinating stories and artifacts. Continue to the iconic U Drop Inn Café, one of the most photographed stops on Route 66, before marveling at the quirky Leaning Tower of Texas—an off-kilter water tower cleverly designed as a roadside attraction. Along the way to Amarillo, enjoy more classic Route 66 sights before tonight’s big finale: dinner at the legendary Big Texan Steak Ranch. Known for its saloon-style atmosphere, over-the-top Western décor, and the famous 72-ounce steak challenge, it’s a Texas experience you’ll never forget. (B, D)

Day 7 – Ghost Towns, Santa Fe & Mountain Views
Your Route 66 adventure continues westward with iconic stops along the way. Visit the colorful Cadillac Ranch, where half-buried cars create one of the most famous roadside art installations in America. At Glenrio, explore a true Route 66 ghost town—stand with one foot in Texas and the other in New Mexico as you imagine the road in its heyday. Continue on to Santa Fe, a city rich with Native American art, adobe architecture, and vibrant culture. After time to shop and explore, travel to Albuquerque, New Mexico’s largest city. Tonight, share a memorable group dinner overlooking the dramatic Sandia Mountains—a perfect finale to another day on the Mother Road. (B, D)

Day 8 – From Route 66 to the Great Sand Dunes
Though your Route 66 journey concludes in Albuquerque, the adventure continues as you head north across desert plains, buttes, and into dramatic mountain scenery. Today’s highlight is Great Sand Dunes National Park, where towering dunes rise like mountains themselves—an awe-inspiring and otherworldly landscape unlike anywhere else. After lunch, continue north to Lonetree, just south of Denver. This evening, gather with your fellow travelers for a special Farewell Dinner, celebrating the memories and friendships made along the Mother Road. (B, D)

Day 9 – Golden Spike Tower & Journey Home
On your final leg home, stop at the Union Pacific Railyard—the largest in the world—and take in sweeping views from the Golden Spike Tower, where the sheer scale of America’s rail system is on full display. Then, continue your journey home, arriving this evening with unforgettable memories from the first half of your Route 66 adventure. Part Two awaits in 2026, when the road continues from Albuquerque to Los Angeles! (B)

Reserve online or print the Rt. 66 Part 1: Chicago to Albuquerque Brochure and mail to:

PO Box 751 Bellevue NE 68005