Menu
Avoya Travel Logo
Call
feature image

Highlights of Route 66

16 day tour from Chicago to Los Angeles
Tour Operator
Cosmos
Departures
Oct 03, 2026 – Oct 16, 2027
Prices From
$3,539

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

Tour Map
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

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.

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)

What's Included

Transportation icon
Transportation
Private, deluxe air-conditioned motorcoach while touring with free Wi-Fi.
Meals icon
Meals
7 Breakfasts

Hotels

First-Class

Itinerary Dates & Prices

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 $3,669
Guaranteed
Start Date May 29, 2027
End Date Jun 13, 2027
Our Price $3,769
Guaranteed
Start Date Jun 12, 2027
End Date Jun 27, 2027
Our Price $3,539
Guaranteed
Start Date Jun 19, 2027
End Date Jul 04, 2027
Our Price $3,689
Guaranteed
Start Date Jul 10, 2027
End Date Jul 25, 2027
Our Price $3,789
Guaranteed

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

to be connected with a travel professional today!

Don't Miss the Latest Deals!
Talk to a Vacation Planner
Avoya Travel Logo Mark
Why Choose Avoya?