9Route 66 (Chicago to Santa Monica)

Known as the “Mother Road”, Route 66 is perhaps the most iconic road trip in the United States, offering travelers a journey through Americana. 

Starting in Chicago and stretching across 2,448 miles to Santa Monica, California, Route 66 takes you through eight states and showcases a slice of classic American culture. The highway is famous for its quirky roadside attractions, vintage diners, and retro motels. Along the way, you’ll pass through ghost towns, vibrant cities like St. Louis and Albuquerque, and natural wonders like the Grand Canyon.