
Highlights of Route 66
Follow the legendary Route 66 from Chicago to Los Angeles on a journey across the heart of America. Known as the "Main Street of America," Route 66 connected communities across eight states and became one of the country's most iconic highways. Today, traces of its history live on in roadside attractions, historic towns, and museums dedicated to preserving the spirit of the Mother Road. Travel through Illinois, Missouri, Oklahoma, Texas, New Mexico, Arizona, Nevada, and California while visiting Route 66 landmarks, cultural sites, and communities that helped shape the highway's legacy. Along the way, explore Chicago and Los Angeles, visit the Cherokee Nation Anna Mitchell Welcome & Cultural Center, stop at Cadillac Ranch, and discover the stories behind America's most famous road at several Route 66 museums. The journey also includes a detour to Grand Canyon National Park, where you'll experience one of the country's most spectacular natural landscapes, as well as time in Las Vegas to explore the city's famous resorts, entertainment, and attractions. Optional excursions include visiting Hoover Dam and a rafting adventure through Black Canyon on the Colorado River. Complete your Route 66 adventure in Santa Monica at the historic "End of the Trail" sign before discovering some of Los Angeles' most famous sights, including Hollywood, Beverly Hills, and the Sunset Strip. From roadside Americana and historic landmarks to scenic countryside and iconic cities, this journey celebrates one of the most legendary road trips in American history.
Tour Itinerary

Welcome to Chicago, the start of Route 66! Your Tour Director is available from 3:00 p.m. - 6:00 p.m. to answer questions. After settling into your hotel, enjoy time to explore on your own. Stroll along the Chicago Riverwalk, admire the city’s renowned architecture, or browse the shops and attractions along Michigan Avenue.
Known as the “Windy City,” Chicago is celebrated for its striking architecture, vibrant cultural scene, and rich history. This morning, enjoy a sightseeing tour featuring some of the city’s most recognizable landmarks, including the sign marking the beginning of historic Route 66. The afternoon is free to explore. Visit the Skydeck on the 103rd-floor of the Willis Tower (formerly Sears Tower), stroll along the Magnificent Mile, sample Chicago’s famous deep-dish pizza, or choose an optional river cruise for a unique perspective on the city’s renowned architecture.
This morning, begin your Route 66 journey with a visit to the Route 66 Hall of Fame & Museum in Pontiac, housed in a historic fire station. Explore exhibits, photographs, maps, and memorabilia that celebrate the history, people, and places that made Route 66 America’s most famous highway. Continue to Springfield, the capital of Illinois, for a visit to the Abraham Lincoln Presidential Museum, where interactive exhibits and artifacts bring the story of the 16th U.S. president to life.
Cross the mighty Mississippi River and continue to St. Louis, known as the “Gateway to the West.” An orientation tour introduces the city before a visit to Gateway Arch National Park. Ride to the top of the 630-foot-tall Arch for panoramic views of the city and the Mississippi River below. Later, travel along a historic stretch of Route 66 and get the chance to sample Ted Drewes Frozen Custard, a Route 66 treat since 1929. (B)
What's Included
Hotels
Itinerary Dates & Prices
Available Tour Deals
The below deals may be applicable to this tour. Restrictions apply. Need help figuring out the right deal for you.
Call 1-888-447-8459
- Save favorite vacations & searches
- Early access to promotions
- Exclusive deals, discounts & prices
- Plus more!