Welcome to the iconic starting point of Route 66 in Chicago, Illinois, a journey steeped in Americana and celebrated as the "Main Street of America." Stretching over 2,448 miles all the way to Santa Monica, California, this historic route offers a glimpse into the heart and soul of the United States. Known for its eclectic mix of museums, diners, and natural wonders, Route 66 has captivated travelers and adventurers since its establishment in 1926.

Did you know that Route 66 was one of the original highways within the U.S. Highway System? This legendary route was officially removed from the system in 1985 after it was decided that the new Interstate Highway System would replace it. However, its legacy continues as it remains one of the most famous roads in America, often symbolizing freedom and the great American road trip.

The history of Route 66 is a vivid tapestry that captures the evolution of American road travel. Conceived in response to the growing need for national road networks, its construction began in 1926. The route served as a vital path for those migrating west during the Dust Bowl of the 1930s. It also supported wartime efforts by providing a strategic transport corridor during World War II. These historical events not only shaped the nation but also cemented Route 66's role in American cultural and historical identity.

For those looking to experience Route 66 as locals do, start your journey with a hearty breakfast at Lou Mitchell's Restaurant and Bakery near the beginning of Route 66 in Chicago. Open since 1923, this diner offers a taste of history with its world-famous donuts and "The World's Best Coffee." A lesser-known fact is that early travelers on Route 66 would receive fresh donuts to energize their long journey ahead.

Imagine finding your favorite childhood cartoon characters like Bugs Bunny carved into ancient rocks along Route 66. Surprisingly, at various points along this historic route, travelers can find quirky roadside attractions including giant statues and unique art installations that reflect America’s love for pop culture. These unexpected sights serve not only as fun photo opportunities but also as reminders of how Route 66 has influenced popular culture across generations.

Nearby attractions include The Art Institute of Chicago and Millennium Park. Just a short drive from where Route 66 begins, The Art Institute houses an impressive collection ranging from ancient artifacts to modern art. Millennium Park offers iconic sculptures like Anish Kapoor’s Cloud Gate (affectionately known as "The Bean") and hosts numerous public events throughout the year which embody Chicago’s vibrant cultural scene.