Celebrate 100 years of adventure on Route 66, affectionately known as the “Mother Road.” This iconic route has come to embody freedom, discovery, and the spirit of the open road. Journey with us from Chicago to the Pacific Coast as we trace the historic path that shaped a generation. Along the way, enjoy the nostalgic allure of vintage diners, vibrant neon signs, quirky roadside attractions, and classic mom-and-pop stops that capture the essence of America’s golden age of travel.
DAY 1: WELCOME TO THE WINDY CITY!
Arrive in Chicago and gather with your group and Tour Director for a welcome dinner to kick off your Route 66 adventure! D
DAY 2: CHICAGO, IL
Explore Chicago’s Route 66 landmarks, including the “Begin Route 66” sign and Lou Mitchell’s diner, then travel to Wilmington to see the Gemini Giant, visit the Route 66 Hall of Fame & Museum in Pontiac, and arrive in Springfield, IL, noting historic Rout 66 shields along the way. B, D
DAY 3: GATEWAY TO THE WEST
In Springfield, tour Abraham Lincoln’s home, see where the corn dog-on-a-stick was invented, and pass through classic midwestern towns and diners before reaching St. Louis for a visit to the iconic Gateway Arch, America’s tallest monument. B, D
DAY 4: SPRINGFIELD, MO
Cross the Chain of Rocks Bridge into Missouri, explore Cuba’s murals, stop at the Wagon Wheel Motel and Fanning 66 Outpost with its record-breaking rocking chair, and finish the day surrounded by Route 66 nostalgia in Springfield, MO. B, D
DAY 5: CLAREMORE & CATOOSA, OK
Head into Oklahoma, stopping in Joplin’s Route 66 Mural Park, visiting Ed Galloway’s Totem Pole Park, touring the Will Rogers Memorial Museum in Claremore, and snapping a photo with the Blue Whale of Catoosa! B, D
DAY 6: AMARILLO, TX
Visit the National Route 66 & Transportation Museum in Elk City, Oklahoma, then continue into Texas for a stop at the Art Deco U-Drop Inn Café in Shamrock and a visit to Amarillo’s Cadillac Ranch, where you will drive in a 1955 pink Cadillac simulator before eating dinner at the Big Texan Steak Ranch. B, D
DAY 7: TUCUMCARI, NM
Drive farther out into the west as you cross into New Mexico, stopping at Adrian’s Route 66 midpoint, visiting the Blue Swallow Motel in Tucumcari, and exploring Albuquerque’s unique Route 66 intersections. B, D
DAY 8: ALBUQUEQUE, NM
Enjoy a guided tour of Albuquerque, learning about its 18-mile Route 66 stretch, then spend the afternoon exploring the city at your leisure. B
DAY 9: PETRIFIED FOREST NATIONAL PARK
Head into Arizona to tour the Petrified Forest National Park and the Painted Desert, have lunch at the beautiful Painted Desert Diner before staying overnight at the historic La Posada Hotel in Winslow. B, L
DAY 10: WINSLOW, AZ
Experience a special tour honoring pioneering women of Route 66, visit Winslow’s “Standing on the Corner” park, stop of Jack Rabbit Trading Post, explore Seligman’s retro charm, and pass through the adorable Peach Springs—the inspiration behind Pixar’s Cars. B, D
DAY 11: KINGMAN, AZ
In Kingman, visit the Powerhouse Visitors Center and Arizona Route 66 Museum, watch a Wild West show in Oatman among wild burros, and cross the colorful Mojave Desert into California. B, D
DAY 12: SANTA MONICA, CA & RETURN HOME
Conclude your journey at the California Route 66 Museum in Victorville, visit the first McDonald’s site and Wigwam Motel in San Bernardino, and celebrate at the Santa Monica Pier’s “End of the Trail” sign before heading home with memories of America’s Main Street. B
Quality Accommodations
Night 1: Embassy Suites, Rosemont, IL
Night 2: Drury Inn, Springfield, IL
Night 3: Holiday Inn Route 66, St. Louis, MO
Night 4: Hampton Inn, Springfield, MO
Night 5: Holiday Inn Express, Clinton, OK
Night 6: Fairfield Inn, Amarillo, TX
Nights 7-8: Hyatt Place, Albuquerque, NM (or similar)
Night 9: La Posada Hotel, Winslow, AZ
Night 10: Ramada, Kingman, AZ
Night 11: Fairfield Inn & Suites, Victorville, CA
Dates:
Aug 14-25, 2026
Price Per Person:
Double $3,299
Single $4,155
Pre-/Post Tour Hotel:
Pre Hotel: $185/night
Post Hotel: $220/night
Depart/Return:
Depart: Chicago, IL
Return: Los Angeles, CA
Inclusions:
Free airport shuttle or hotel parking
Welcome Dinner and meals as indicated (B=breakfast, L=lunch, D=dinner)
Fees and tips for included attractions and meals
Luggage handling of one suitcase per person at hotels
Free bottled water on coach
24-hour emergency call service
Arrival Time
Our Welcome Dinner on Day 1 is at our hotel, Embassy Suites Rosemont, starting at 6:30 p.m. We recommend scheduling your flight to the Chicago O’Hare Airport to arrive by 4:00 p.m.
Departure Time
Schedule your flight home to depart the Los Angeles International Airport. Specific timing of flights will be provided 90 days prior to departure.
Airport Transportation / Vehicle Parking
Our starting hotel offers a complimentary shuttle service to/from the Chicago O’Hare International Airport. If you are driving to the starting location, they also offer complimentary parking for the duration of the tour.
Walking Distance
To fully enjoy your vacation, you should be in good physical health and understand there are times when a good deal of walking is involved in our tours. Those who have difficulty walking may not want to take this trip or should discuss their personal situation with their doctor before deciding. You should be able to walk at a steady pace up to a mile at a time for a daily total of three to four miles per day and be able to manage steps to board/de-board the motorcoach several times a day. In addition, please know you may be expected to exit the motorcoach at each stop because local law requires mandatory motorcoach driver breaks.
Due to the lack of proper facilities at some of the farms, ranches, and off-the-beaten-path sites we often visit, we are unable to accommodate walkers and wheelchairs.
Average Temps
August– high of 95° F, low of 60° F
Time Zones
Central, Mountain, and Pacific
Hotel Amenities
Most accommodations arranged by Country Travel Discoveries are equipped with in-room amenities such as a hair dryer, iron, and coffee maker. In addition, some properties may also have a pool, fitness center, or laundry facilities.
Additional Information
A total of three mailings are sent to assist you in preparing for your tour, including information sent upon receipt of your reservation.
Dress on tour is casual. Sunscreen, sunglasses, hat, visors, and comfortable walking shoes will add to your enjoyment of this tour. As this tour will travel through multiple states within the United States, it is recommended to pack a variety of layers to accommodate for potential temperature ranges.
Travel Protection Available?
Yes, see CountryTravelDiscoveries.com/TravelProtectionPlan.
