Route 66 Turns 100 in 2026, and It All Begins in Chicago
Why Chicago Is the Starting Point of America’s Most Iconic Road
For nearly a century, Route 66 has symbolized freedom, adventure, and the open road. Known as the “Mother Road,” this legendary highway stretches more than 2,400 miles across the United States, and it all begins in Chicago.
In 2026, Chicago is celebrating the 100th anniversary of Route 66, marking a full century since the road first connected the Midwest to the Pacific Coast.
How Route 66 Came to Life
Route 66 was created during a time when America was shifting from railroads to automobiles.
In the 1920s, highway planner Cyrus Avery proposed a route that would connect Chicago to Los Angeles, helping boost commerce and travel across the country. His vision was to link existing roads and small-town main streets into one continuous highway.
The result was a 2,448-mile route from Chicago to California, officially established in 1926.
Why the Route Starts in Chicago
Chicago was the natural starting point.
At the time, the city was one of the most important transportation hubs in the country, with railroads, highways, and waterways all intersecting here. Travelers heading west already passed through Chicago, making it the perfect gateway to the rest of the country.
The original Route 66 began at Jackson Boulevard and Michigan Avenue, right in the heart of downtown.
Today, Chicago has also recognized Navy Pier as the official centennial starting point, giving the route a new lakefront beginning for its 100-year celebration.
The Golden Era of the “Mother Road”
Route 66 played a major role in American history.
During the 1930s, families fleeing the Dust Bowl traveled west along the highway in search of better opportunities. More than half a million people made the journey, turning Route 66 into a symbol of hope and survival.
By the 1950s, the road became a cultural icon. Road trips exploded in popularity, and Route 66 was lined with diners, motels, gas stations, and roadside attractions that defined American travel.
It also became part of pop culture through books like The Grapes of Wrath, films, and the famous song “(Get Your Kicks on) Route 66.”
A More Complex History: The Green Book Era
Not all travelers experienced Route 66 the same way.
During segregation, Black travelers relied on the Negro Motorist Green Book, a guide that listed safe places to stay, eat, and refuel along the route.
Several Chicago landmarks were included in the guide, including:
Navy Pier
The Art Institute of Chicago
The Field Museum
The Chicago Cultural Center
These locations served as important safe spaces during a time when travel was far more restricted for many Americans.
The Decline and Revival of Route 66
As the Interstate Highway System expanded, Route 66 began to fade.
Faster highways replaced the original road, and in 1985, Route 66 was officially decommissioned. Many towns along the route saw a decline as traffic shifted elsewhere.
But the story didn’t end there.
In recent decades, Route 66 has experienced a revival. Travelers, historians, and communities have restored landmarks and embraced its legacy, turning it into a heritage route that continues to attract visitors from around the world.
Iconic Route 66 Stops in Chicago
Chicago’s stretch of Route 66 is filled with historic and cultural landmarks that still draw visitors today:
Navy Pier – The newly recognized centennial starting point
Original Route 66 Begin Sign – A must-visit photo spot downtown
Lou Mitchell’s – A classic diner known as the “first stop” on the route
The Berghoff – One of Chicago’s oldest restaurants
Route 66 mural at Lulu’s Hot Dogs – A colorful tribute to the road
These stops give travelers a glimpse into the past while keeping the spirit of Route 66 alive.
Why Route 66 Still Matters Today
Route 66 is more than just a historic highway. It represents a piece of American identity.
For Chicago, it reinforces the city’s role as a starting point, not just geographically, but culturally. It’s where journeys begin, where stories start, and where one of the most iconic roads in the world continues to inspire travelers.
Bottom Line
As Route 66 celebrates its 100th anniversary, Chicago remains at the center of its story. From its downtown origins to its modern-day revival, the Mother Road continues to symbolize freedom, discovery, and the enduring appeal of the open road.
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