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Highlights of Route 66
16 day tour from Chicago to Los Angeles
Tour Operator
Cosmos
Departures
Oct 3, 2026
–
Oct 16, 2027
Prices From
$3,619
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 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
Day 1
CHICAGO
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.
Day 2
CHICAGO K
nown 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.
Day 3
CHICAGO–PONTIAC–SPRINGFIELD
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.
Day 4
SPRINGFIELD–ST. LOUIS
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)
Day 5
ST. LOUIS–JOPLIN
Travel through the rolling countryside of Missouri, following portions of historic Route 66. Along the way, pass small towns, classic roadside attractions, and reminders of the highway’s golden age. Arrive in Joplin, a city with deep Route 66 roots and a colorful past. Learn about the area’s history, including its connection to the infamous outlaws Bonnie and Clyde, who briefly sought refuge here during their crime spree across the American Midwest. (B)
Day 6
JOPLIN–TULSA–OKLAHOMA CITY
After a brief drive through Kansas, enter Oklahoma, once known as Indian Territory and home to the Cherokee Nation. Visit the Cherokee Nation Anna Mitchell Welcome & Cultural Center to learn about Cherokee history, culture, and contemporary life through exhibits, artwork, and interpretive displays. Continue to Tulsa, where you’ll see the “East Meets West” sculpture honoring Cyrus Avery, widely recognized as the “Father of Route 66.” Later, arrive in Oklahoma City for an overnight stay. (B)
Day 7
OKLAHOMA CITY–ELK CITY–AMARILLO
Begin the day with a sightseeing tour of Oklahoma City, the capital of Oklahoma, including a stop at the moving Oklahoma City National Memorial honoring those who were killed, those who survived and those changed forever by the April 19, 1995, bombing of the Alfred P. Murrah Federal Building. Continue to Elk City for a visit to the National Route 66 Museum, where exhibits trace the history, people, and communities that shaped America’s most famous highway crossing eight states. Travel west across the Texas Panhandle to Amarillo, known for its ranching heritage and Route 66 connections. (B)
Day 8
AMARILLO–TUCUMCARI–ALBUQUERQUE
Depart Amarillo and stop at Cadillac Ranch, the iconic roadside art installation featuring 10 colorful Cadillacs buried nose-first in a Texas field. Continue to Adrian, the midpoint of historic Route 66, before crossing into New Mexico. Visit Russell's Car Museum, home to a collection of classic automobiles, vintage gas pumps, and Route 66 memorabilia. In Tucumcari, browse souvenirs at Tee Pee Curios, a Route 66 landmark since 1944, and see the famous Blue Swallow Motel, which has welcomed travelers along the Mother Road since 1939. Later, arrive in Albuquerque and travel along Central Avenue, where many historic Route 66-era buildings, signs, and businesses remain. Then enjoy free time to explore Historic Old Town, known for its adobe architecture, Spanish Colonial heritage, and lively central plaza. (B)
Day 9
ALBUQUERQUE
Enjoy a day at leisure in Albuquerque, a city where Native American, Hispanic, and Anglo influences have shaped a rich cultural heritage. Explore Historic Old Town, the site of the city’s original settlement, or visit one of Albuquerque’s many museums, including the New Mexico Museum of Natural History & Science, the Albuquerque Museum, or the Indian Pueblo Cultural Center. You may also choose an optional narrated trolley tour for an introduction to some of Albuquerque’s most notable landmarks, neighborhoods, and Route 66 sites.
Day 10
ALBUQUERQUE–GALLUP–WINSLOW–WILLIAMS
Depart Albuquerque and stop to learn about the rich volcanic landscape at El Malpais National Monument Visitor Center, where lava flows, sandstone bluffs, and rugged badlands create a striking landscape shaped by centuries of volcanic activity. Cross the Continental Divide and continue to Gallup, a community with deep Native American heritage and strong connections to the Navajo, Hopi, Zuni, and other Indigenous cultures of the Southwest. Then stop in Winslow, Arizona the sleepy Route 66 town made famous by the Eagles' hit song Take It Easy. Later, arrive in Williams, a historic Route 66 town and gateway to Grand Canyon National Park, for a two-night stay. Listed on the National Register of Historic Places, Williams features a walkable downtown filled with Route 66 landmarks, western heritage, shops, restaurants, and historic buildings.
Day 11
WILLIAMS. EXCURSION TO GRAND CANYON NATIONAL PARK
Leave Route 66 behind for a day to visit Grand Canyon National Park. Explore the South Rim and take in sweeping views of one of North America's most iconic landscapes, carved by the Colorado River over millions of years. Keep watch for wildlife, including elk that are often seen in the park's forested areas. For a different perspective, consider an optional helicopter flightseeing excursion above the canyon with thrilling aerial views. Return to Williams for a free evening. Explore the town's historic Route 66 district, browse local shops, eat at a vintage diner, or stroll past the glowing neon signs that line the preserved 1940s-era Motel Row. (CB)
Day 12
WILLIAMS–SELIGMAN–LAS VEGAS
Depart Williams and travel to Seligman, a community that played an important role in preserving and revitalizing historic Route 66. Continue west before leaving the Mother Road behind for a visit to Las Vegas. Upon arrival, enjoy an orientation tour featuring some of the city's famous resorts, themed hotels, and landmarks along the Las Vegas Strip. This evening is free to explore. Enjoy an optional night on the town that includes dinner and a live show celebrating the entertainers who helped shape Las Vegas' rich entertainment history followed by a visit to the Freemont Street Experience, a lively district known for its illuminated canopy, street performers, and historic casinos. (CB)
Day 13
LAS VEGAS
Enjoy a full day at leisure to experience Las Vegas your way. Explore the famous Las Vegas Strip, relax by the pool, shop, or visit some of the city's most distinctive attractions. Take a gondola ride through the canals at The Venetian, admire the seasonal botanical displays at the Bellagio Conservatory & Botanical Gardens, or discover the many other themed resorts that have made Las Vegas one of the world's most recognizable destinations. Or join an optional excursion to see nearby Hoover Dam, one of America's most impressive engineering achievements, and learn about this towering marvel.
Day 14
LAS VEGAS–VICTORVILLE–LOS ANGELES
Depart Las Vegas and travel across the Mojave Desert and the San Bernardino Mountains en route to Los Angeles. Along the way, visit the California Route 66 Museum, where exhibits celebrate the history and nostalgia of America's most famous highway, including a 1950s diner, a VW Love Bus, and a 1917 Ford Model T. Continue to Santa Monica, home to the historic "End of the Trail" sign marking the end of this legendary road. Take time to reflect on your journey across eight states before arriving in Los Angeles for a two-night stay.
Day 15
LOS ANGELES D
iscover some of Los Angeles' most iconic neighborhoods on a morning sightseeing tour. Visit Beverly Hills, travel along the Sunset Strip, and explore Hollywood, where the stars embedded in Hollywood Boulevard's Walk of Fame honor some of the entertainment industry's most influential figures. The afternoon is free to explore on your own. Perhaps join the optional Warner Bros. Studio Tour for a behind-the-scenes look at film and television production, including soundstages, backlots, and locations featured in popular movies and television shows.
Day 16
LOS ANGELES
Your vacation ends this morning. You may choose to extend your vacation with extra nights and explore Los Angeles further.
What's Included
Transportation
Private, deluxe air-conditioned motorcoach while touring with free Wi-Fi.
Meals
7 Breakfasts
Hotels
Courtyard Chicago Downtown/Magnificent Mile
First-Class
President Abraham Lincoln Springfield, a DoubleTree by Hilton
First-Class
Pear Tree Inn St. Louis Near Union Station
Superior Tourist-Class
Drury Inn & Suites Joplin
Moderate First-Class
Sheraton Oklahoma City Downtown Hotel
Superior First-Class
Country Inn & Suites Amarillo West
Superior Tourist-Class
Best Western Plus Rio Grande Albuquerque
Moderate First-Class
La Quinta Inn and Suites-Grand Canyon Area
Superior Tourist-Class
Sahara Las Vegas
Moderate Deluxe
Westin Bonaventure
Superior First-Class
Itinerary Dates & Prices
Start Date
End Date
Our Price
Guaranteed
Start Date
Oct 03, 2026
End Date
Oct 18, 2026
Our Price
$3,829
Guaranteed
Start Date
May 08, 2027
End Date
May 23, 2027
Our Price
$3,619
Guaranteed
Start Date
May 29, 2027
End Date
Jun 13, 2027
Our Price
$3,619
Guaranteed
Start Date
Jun 12, 2027
End Date
Jun 27, 2027
Our Price
$3,639
Guaranteed
Start Date
Jun 19, 2027
End Date
Jul 04, 2027
Our Price
$3,639
Guaranteed
Start Date
Jul 10, 2027
End Date
Jul 25, 2027
Our Price
$3,639
Guaranteed
Start Date
Aug 28, 2027
End Date
Sep 12, 2027
Our Price
$3,619
Guaranteed
Start Date
Sep 11, 2027
End Date
Sep 26, 2027
Our Price
$3,659
Guaranteed
Start Date
Sep 18, 2027
End Date
Oct 03, 2027
Our Price
$3,659
Guaranteed
Start Date
Oct 02, 2027
End Date
Oct 17, 2027
Our Price
$3,619
Guaranteed
Start Date
Oct 16, 2027
End Date
Oct 31, 2027
Our Price
$3,619
Guaranteed
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