In downtown Chicago, at the intersection of Adams Street and Michigan Avenue, a modest sign marks the starting point of U.S. Route 66, one of America’s most historic highways. Established in 1926, Route 66 extends over 2,400 miles from Chicago to Santa Monica, California, winding through diverse landscapes including deserts, plains, and mountains.

The highway was introduced during a period of significant change in American society, as the expanding use of automobiles reshaped travel and commerce. Chicago’s role as a major commercial and transportation hub made it a natural point of origin for the route, which stretches southwest from the city across Illinois farmland and continues through Missouri, Oklahoma, Texas, New Mexico, Arizona, and finally reaches the West Coast.

Route 66 played a critical role during the 1930s, serving as a corridor for thousands of migrants moving westward in pursuit of economic opportunity during the Great Depression. The road came to embody themes of hope, resilience, and the quest for a better life. Following World War II, the highway gained cultural prominence as a symbol of freedom and adventure, frequently celebrated in music, film, and popular culture.

Although the highway was officially decommissioned in 1985, its cultural and historical significance persists. Chicago actively maintains its connection to Route 66, attracting visitors from around the world who gather at the starting point sign. Whether embarking on a full journey along the historic road or visiting briefly, travelers engage with a landscape dotted with period landmarks, restaurants, and attractions that reflect the legacy of the "Mother Road."

Today, Route 66 remains an enduring emblem of American exploration and identity, its story rooted in the city of Chicago where the journey begins.