Few landmarks truly capture the American spirit like Route 66. Known as the “Mother Road,” it has been a longstanding symbol of freedom, and opportunity within the United States of America. Stretching cross country from Chicago to Santa Monica, this historic roadway has played an important role in shaping national culture and Chicago’s identity as the city where it all began. In 2026, Route 66 reaches a major milestone with its 100th anniversary! As centennial celebrations kick off, it’s a good time to delve into the highway’s unique origination and history. 

The Birth of Route 66

Route 66 was officially established in 1926 as part of the U.S. Numbered Highway System. This system was designed to connect rural communities with major cites to increase accessible travel. Route 66 ran approximately 2,400 miles from Chicago, Illinois, to Santa Monica in California.

The road was revolutionary for its time! It provided a reliable, continuous route for travelers, truckers, and migrants, linking the Midwest to the West Coast. 

During the Great Depression, Route 66 became a lifeline for thousands of families heading west in search of work and opportunity. This road and its importance became immortalized by famous author John Steinbeck, who famously called it the “Mother Road.”

Chicago: The Starting Point of an American Icon

Chicago holds a special place in Route 66 history as its eastern starting point. Traditionally beginning at Jackson Boulevard and Michigan Avenue, the city marked the gateway to a cross-country journey that would be the start of countless adventures over the years.

As a major transportation hub in the early 20th century, Chicago was the ideal starting point for the route. After the highway was established, the road effectively extended Chicago’s influence across the country, connecting its economy and culture to distant regions.

With this expansion, Route 66 significantly contributed to Chicago’s growth as a tourism and cultural destination. Travelers beginning their journey in the city often explored its neighborhoods, architecture, and dining scene before heading west. This influx of visitors helped boost local businesses and reinforced Chicago’s reputation as a vibrant, and welcoming city!

Beyond economics, Route 66 had an influence on music, literature, and pop culture. Many songs, films, and books have kept the spirit of the road alive, with Chicago often serving as the narrative starting point for these journeys.

In 2026, the city is reimagining this historic starting point by designate Navy Pier as a symbolic new beginning for Route 66 as part of the centennial celebrations. This transition demonstrates how the road’s legacy continues to evolve!

Decline and Preservation

By the mid-20th century, the rise of the Interstate Highway System led to the gradual decline of Route 66. Faster, more direct highways replaced much of the original route, and in 1985 it was officially decommissioned.

However, the story didn’t end there. Preservation efforts began almost immediately, with communities, historians, and enthusiasts working to protect the road’s legacy. In Illinois and especially in The Windy City, Route 66 became a symbol of nostalgia and tourism. Scenic byways, museums, and historic markers now celebrate its enduring importance.

The 2026 Centennial Celebration

The year 2026 marks the 100th anniversary of Route 66! Across the country, and especially in Chicago, celebrations are underway to honor the road’s historic impact.

As the official starting point, Chicago is playing a central role in these festivities by hosting events, exhibitions, and cultural programs throughout the year, inviting visitors to rediscover the origins of this legendary highway. If you’re in town, check out any ongoing celebrations and pop into Navy Pier's Route 66 store for a bit of memorabilia or to kickstart your own cross-country adventure!

As the highway reaches its 100th anniversary in 2026, the city stands proudly at the beginning of this iconic journey, celebrating its role in one of the most enduring stories in American history. Whether through preservation efforts or modern celebrations, Chicago ensures that the spirit of Route 66 will continue to inspire future generations.