6Route 66 (Chicago to Santa Monica)

Known as the “Main Street of America,” Route 66 is one of the most legendary road trips in the United States. This historic highway stretches from Chicago, Illinois, to Santa Monica, California, spanning more than 2,400 miles. Along the way, travelers encounter a wide variety of landscapes, from the sprawling plains of the Midwest to the desert landscapes of the Southwest, and eventually, the sunny coasts of California.

Route 66 is more than just a road; it’s a journey through American history and culture. The route is dotted with retro diners, quirky roadside attractions, and small towns that have preserved a nostalgic, 1950s-era atmosphere. Traveling Route 66 allows visitors to experience the essence of the American road trip, with stops at iconic locations like Cadillac Ranch in Texas, the Wigwam Motels, and even detours to major attractions such as the Grand Canyon. The route embodies a sense of adventure and the open road, making it an essential trip for anyone seeking the ultimate U.S. road trip experience.