If you’re a first-time visitor or a seasoned Chicagoan, the city skyline never ceases to impress. Our advice is to go between May and September. That’s when the city comes alive with outdoor food and music festivals.
If you can dream it, we can make it happen...
Mile After Magnificent Mile: A Taste of Route 66 Fly Drive
Travel through the state of Illinois getting a taste of Route 66 and experience mile after magnificent mile.
Boston & Chicago
Visit two of America’s most famous cities on this incredible holiday to East Coast USA.
3 Nights in The Windy City
Historic Route 66 Fly Drive
Get your kicks along America’s mother road and most historic highway, Route 66! Stroll through quaint small towns o...
New York & Chicago
Immerse yourself in both of these vibrant cities, from the five boroughs head in The Windy City or visit the Brooklyn...
Heart of the Nation – Route 66 Fly Drive
A road trip across America is something that most people long to do and with this Drive America option you can drive ...
Las Vegas & Chicago
A popular twin city trip combining the East Coast's windy city and the hot desert in Vegas
Classic Route 66 Escorted Tour
Explore historic Route 66, taking in Chicago, the Old West in Oklahoma or kick up your heels in Albuquerque.
Historic Route 66 Adventure
Immortalized in folklore, film and song, Route 66 remains the iconic symbol of the great American road trip
Route 66 by Rail
Board Amtrak® and ride the rails along historic Route 66!
California Coast by Rail
Travel down the gorgeous California Coast as you venture from San Francisco to San Diego, with stops in Paso Robles a...