10 Best Road Trip Stops Along America's Iconic Route 66
Route 66, often referred to as the "Main Street of America," is more than just a highway; it is an emblem of freedom and exploration, capturing the imagination of travelers for nearly a century. Spanning approximately 2,448 miles from Chicago, Illinois, to Santa Monica, California, this iconic road is a symbol of the American spirit. It traverses eight states, each offering a unique tapestry of landscapes, cultures, and histories. The road invites adventurers to embark on a journey through small towns, bustling cities, and picturesque countryside, capturing the essence of America's heartland. As we explore these 10 must-see stops, we'll uncover the hidden gems and iconic landmarks that make Route 66 a journey worth taking. So buckle up and prepare for a journey through America's heartland, where every mile brings a new story and every stop is a chapter in the great American road trip.
1. Chicago, Illinois - The Starting Point

The journey along Route 66 begins in Chicago, Illinois, a city known for its architectural marvels, vibrant culture, and rich history. As the starting point of this legendary road, Chicago offers travelers a dynamic blend of urban excitement and historical significance. Before hitting the road, take time to explore the city's iconic landmarks, such as the Willis Tower, Millennium Park, and the Art Institute of Chicago. Each of these sites provides a glimpse into the city's diverse cultural landscape and its role as a major hub of American industry and innovation. Chicago's connection to Route 66 is deeply rooted in its history as a transportation and commerce center. The city served as a gateway for travelers heading west, and its bustling streets were the launching point for countless journeys along the Mother Road. Visitors can explore the Route 66 Begin sign on Adams Street, a symbolic marker that signifies the start of the adventure. The city's vibrant neighborhoods, such as Wicker Park and Logan Square, offer a taste of local life, with eclectic dining options, unique shops, and lively entertainment venues.
As travelers prepare to embark on their Route 66 odyssey, Chicago sets the tone for the journey ahead. The city's rich history, diverse culture, and dynamic energy provide a fitting backdrop for the start of an adventure that promises to be both thrilling and transformative. Whether you're exploring the city's iconic landmarks or delving into its vibrant neighborhoods, Chicago offers a captivating introduction to the journey along Route 66.