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Highlights of Route 66
16 day tour from Chicago to Los Angeles
Tour Operator
Cosmos
Departures
May 10, 2025
–
Oct 3, 2026
Prices From
$3,259
Get your kicks on Route 66 with a legendary trip across America. This historic route, which was called the “Main Street of America” for more than 50 years before the advent of the US Interstate system, begins in Chicago, travels through eight states, and ends in Los Angeles. On this trip down memory lane, you’ll travel to the major cities along Route 66, visit Route 66 museums, and step back in time to when the journey was part of the fun! Visit Pontiac’s Route 66 Hall of Fame & Museum, which features memorabilia from the heyday of Route 66. In Springfield, visit the Abraham Lincoln Presidenti
Tour Itinerary
Day 1
CHICAGO
Welcome to Chicago, the start of Route 66! Your Tour Director is on hand from 3pm-6pm to answer questions. Once settled into your hotel, perhaps start exploring the city’s amazing architecture via the 1.25-mile Riverwalk along the Chicago River or do some shopping at the many well-known retail destinations along Michigan Avenue.
Day 2
CHICAGO
Known as the “Windy City,” Chicago is home to iconic architecture, including one of America’s tallest buildings, notorious gangster Al Capone, and countless jazz and blues clubs. Oh, and deep-dish pizza, of course! Get to know this exciting city on a morning sightseeing tour that includes the sign marking the start of historic Route 66. Spend a free afternoon exploring Chi Town—perhaps a visit to the 103rd-floor Skydeck of the Willis Tower (formerly Sears Tower), a walk along the Magnificent Mile, or an optional river cruise for a different view of the city’s celebrated architecture. (CB)
Day 3
CHICAGO–PONTIAC–SPRINGFIELD
This morning, immerse yourself in Route 66 memorabilia. Visit the Route 66 Hall of Fame & Museum in Pontiac, housed in a historic fire station. See the large maps that will sketch out your Route 66 adventure for the coming days and enjoy the nostalgic photos and postcards from the “Mother Road’s” heyday. Then on to Springfield, the capital of Illinois, where we will visit the Abraham Lincoln Presidential Museum. (CB)
Day 4
SPRINGFIELD–ST. LOUIS
Cross the mighty Mississippi River and continue to St. Louis, “Gateway to the West.” Your orientation tour includes towering Gateway Arch National Park. Ascend to the top of the 630-foot-tall arch for a panoramic view of the city and river. Then drive along an original stretch of Route 66 and get the chance to savor some Ted Drewes Frozen Custard, a Route 66 treat since 1929. (B)
What's Included
Transportation
Private, deluxe air-conditioned motorcoach while touring with free Wi-Fi.
Meals
9 Breakfasts
Hotels
Hotel Saint Clair
Superior Tourist-Class
Drury Inn & Suites Springfield
Pear Tree Inn St. Louis Convention Center
Drury Inn & Suites Joplin
Sheraton Oklahoma City Downtown Hotel
Country Inn & Suites Amarillo West
Best Western Plus Rio Grande Albuquerque
La Quinta Inn and Suites-Grand Canyon Area
Sahara Las Vegas
Westin Bonaventure
Itinerary Dates & Prices
Start Date
End Date
Our Price
Guaranteed
Start Date
May 10, 2025
End Date
May 25, 2025
Our Price
$3,429
Guaranteed
Start Date
May 24, 2025
End Date
Jun 08, 2025
Our Price
$3,429
Guaranteed
Start Date
Jun 07, 2025
End Date
Jun 22, 2025
Our Price
$3,429
Guaranteed
Start Date
Jul 05, 2025
End Date
Jul 20, 2025
Our Price
$3,259
Guaranteed
Start Date
Aug 23, 2025
End Date
Sep 07, 2025
Our Price
$3,379
Guaranteed
Start Date
Aug 30, 2025
End Date
Sep 14, 2025
Our Price
$3,429
Guaranteed
Available Tour Deals
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