This 16-day Route 66 self-drive tour takes you from coast to coast, Chicago to Los Angeles, and features attractions both historic and quirky, as you might expect from America’s famous “Mother Road.” The route holds a special place in American hearts and history, evoking a simpler time when the automobile brought freedom to millions of travellers and tourists. 

Your journey takes you from Chicago to Kansas, Texas to New Mexico and then Las Vegas, and onward to the California coast. Along the way, visit Amarillo’s Cadillac Ranch, stroll UNESCO-designated Santa Fe, experience Arizona’s Petrified Forest, visit two natural wonders – the Grand Canyon and the Hoover Dam – let loose in Las Vegas, and photograph the Route 66 “End of the Trail” sign in Santa Monica. Finish up by claiming your commemorative Route 66 certificate.

Arrive in Chicago on Day 1 and check in to your hotel. Wake early to explore the magnificent Windy City, beginning with the corner of Michigan and Adams, the official start of Route 66. Order some silver dollar pancakes at Lou Mitchell’s diner, a perennial route favourite since 1926. Stroll the lakefront, do some shopping, visit Navy Pier, or book a tour of the city’s justly-famous architectural treasures, including Willis Tower. End the night at a hopping live music venue.

It’s time to head off for St. Louis, Missouri, so pick up your rental car and head east, travelling through golden cornfields and prairies. Stop for a photo of the larger-than-life green Gemini Giant, or Atlanta’s Bunyan Giant. In Springfield, Illinois, try a Cozy Dog Drive-In corn dog and visit the Lincoln Home National Historic Site. Once in St. Louis, visit a historic site such as the 630-foot tall Gateway Arch.

Southern Missouri takes you through the rolling hills of the Ozark Highlands to Springfield, heralded as the birthplace of Route 66. En route, take a cue from bandit Jesse James and visit Meramec Caverns, one of the rarest and largest cave formations in the world: Jesse once hid out here.

The 380-mile Oklahoma section of Route 66 features such endearing attractions as a 20-foot tall cement Blue Whale in Catoosa and the Cyrus Avery Route 66 Memorial Bridge. In Oklahoma City, look for more Route 66 tributes in the form of classic motels, gas stations and vintage theatres. Head out later for some classic American BBQ or a juicy steak.
Crossing the prairie, rolling hills, and canyons of the Texas Panhandle, your next destination is the Oklahoma Route 66 Museum in Clinton. View the re-created diner, gleaming vintage cars, and replica vintage gas station. The 1930s Tower Station and U-Drop Inn Café are next, in all their pink Art Deco glory. Like your steaks on the big side? Consider the 72-ounce steak challenge at Big Texas Steak Ranch upon arrival in Amarillo.

Day 7 takes you from Amarillo to Albuquerque, New Mexico with a pit stop at the quirky Cadillac Ranch. Lovely Albuquerque sits on the River Grande and its Central Avenue is considered a treasure trove of Route 66 landmarks. Visit historic Old Town and the Indian Pueblo Cultural Center. Then spend your eighth day on a side trip to beautiful Santa Fe, famous for its Pueblo-style architecture, art galleries, markets, and the 17th-century Palace of the Governors museums. Santa Fe is a food lover’s dream: try a spicy New Mexican chile, buffalo tenderloin, or a silky tortilla soup for dinner.

Arizona welcomes you next. Be sure to visit the Petrified Forest National Park, assemblies of petrified wood, historic structures, and archaeological sites. Relish the peace and beauty of the grassland as you hike from scenic Tawa Point to the Painted Desert Visitor Center, or walk around the remains of a 100-room pueblo occupied by the ancestral Puebloan people over 600 years ago.

In historic Wild West Holbrook, Arizona – “the town too tough for women and churches” – stop at the postcard-worthy Wigwam Motel, with its steel and concrete 1950’s teepees. Yes, you can actually stay at this classic piece of American road trip culture. Pass by Meteor City, Flagstaff, and Williams en route to Grand Canyon National Park where you will spend the afternoon exploring the South Rim of the canyon, walking part of the Rim Trail or creating memories at a Photo Hot Spot.

The imposing Hoover Dam is next, before continuing on to Las Vegas for a bit of culture, Nevada style. Spend your thirteenth day sunning by the pool, throwing some dice, shopping, strolling The Strip, or experiencing the exhilarating immersive attraction, FlyOver. Visit a distillery or cocktail bar or dine at one of Vegas’ almost 3,000+ restaurants (800 of them, fine dining).

Head across the Mojave Desert for the California coast today, stopping at Calico Ghost Town, a historic silver mining town for a trip on the Calico Odessa Railroad, or a gold panning experience. Rejoin Route 66 in historic Barstow and visit the Route 66 Mother Road Museum. Continue through Pasadena, Los Angeles, West Hollywood, and Beverly Hills to Santa Monica to proudly view the “End of the Trail” Route 66 sign on Santa Monica’s Pier.

Enjoy a final day of minimal driving. Stroll the beaches of Santa Monica or shop at Third Street Promenade, or head into L.A. for a Universal Studios tour or try out the thrilling new Star Wars ride at Disneyland Park. The next day, return your rental car and head out for home, knowing you successfully drove historic Route 66.

• Begin your epic Route 66 adventure in Chicago, exploring the city’s iconic skyline and vibrant culture.
• Cruise through Missouri’s rolling Ozark hills, discovering roadside gems like Meramec Caverns and the Gateway Arch.
• Experience the quirky Americana of Oklahoma and Texas, from vintage diners to Amarillo’s Cadillac Ranch.
• Explore New Mexico’s adobe charm in Santa Fe and the colourful landscapes of Arizona’s Petrified Forest.
• End your journey at Santa Monica Pier, celebrating your coast-to-coast drive from Chicago to Los Angeles.

• 16 days Intermediate Car Rental with unlimited mileage (Mazda 3 or similar)
• Detailed day-by-day itinerary
• 2 nights premium accommodations in Chicago
• 1 night premium accommodations in St. Louis
• 1 night premium accommodations in Springfield
• 1 night premium accommodations in Oklahoma City
• 1 night premium accommodations in Amarillo
• 3 nights premium accommodations in Albuquerque
• 1 night premium accommodations in Holbrook
• 1 night premium accommodations in Grand Canyon/Williams
• 2 nights premium  accommodations in Las Vegas
• 2 nights premium accommodations in Los Angeles

• Car rental insurance
• Travel insurance
• International and domestic airfare & airfare taxes
• Entrance fees to sites not explicitly listed as included
• Meals and beverages not mentioned
• Road tolls
• Gratuities
• Items of a personal nature
• Passport & Visa fees if applicable