Route 66 in Chicago: Guide, Events & Tour Specials

Route 66 is the ultimate American road trip — and it all starts in Chicago.
In 2026, Chicago will celebrate the 100th anniversary of this iconic route. Learn more about Route 66 and upcoming centennial celebrations in Chicago.
Take advantage of limited-time deals, hotel packages, special tours, and more.
Route 66 Road Trip package
Route 66 Package: 100 Years on the Road
Route 66: Where it all Began package
A Taste of Route 66 tour
Route 66 Neighborhoods by Trolley tour
Get Your Kicks Near Route 66 package
Loews on 66: From the Chicago Skyline to the Gateway Arch
Route 66 Package: 100 Years on the Road
This two-day itinerary will immerse you in Route 66’s legacy, featuring retro diners, historic landmarks, and a big dose of Americana.
Chicago holds the honor of being home to the beginning of the legendary Route 66. Since 1955, the starting point stood at the intersection of Adams Street and Michigan Avenue across from the Art Institute of Chicago.
In 2026, the route was extended to Chicago’s Navy Pier. This centennial starting point creates an eight-state “pier-to-pier” connection with Santa Monica Pier in California, the official end point of the route.
Route 66 offers a true taste of America — and the culinary adventure kicks off here in Chicago.
Sample some of the city’s best bites as you explore the start of the legendary route, including the Chicago’s most iconic culinary creations like Italian beef, deep dish pizza, and the Original Rainbow Cone.
Known as “The Main Street of America,” this iconic route stretches more than 2,400 miles from Chicago.
Over the years, the road has become a bucket-list experience for road trippers, history lovers, and anyone looking to immerse themselves in classic Americana.
Learn more about this historic route, including how it got its start, its evolution over the years, and how you can experience it for yourself.
Discover how the road has shaped the stories of the many Chicago communities it touches.
In 1916, Cook County Hospital emerged as an important establishment for the Tri-Taylor neighborhood in Chicago. This imposing structure, characterized by the Beaux-Arts style of architecture, took root at the intersection of Ogden Avenue, formerly known as Route 66, and Roosevelt Road. This Near West Side area was home to a large Italian community until the 1940s.
Open to those with limited financial means, Cook County Hospital, known simply as “County,” would become one of the world’s busiest charity hospitals, eventually treating an estimated 83,000 patients a year during the 1950s. Ambulances carrying patients from all over the city would speed down the well-paved roads of Route 66 to reach “County.”Cook County Hospital was one of the most recognizable, architecturally distinguished structures on Chicago’s stretch of Route 66. As the years passed, this hospital also became the anchor of the 560-acre Illinois Medical Center District, the nation’s largest concentration of hospitals and research institutions. Established by the 62nd Illinois General Assembly in 1941, the medical district originally included the University of Illinois General Hospital, Cook County School of Nursing, Cook County Hospital, Presbyterian Hospital, Rush Medical College, and Loyola Medical School. The West Side Veterans Administration Hospital, now known as the Jesse Brown VA Medical Center, was later added in 1953. In 2002, “County” closed and was replaced by John H. Stroger Hospital, one of many modern institutions in the now-thriving IL Medical Center District. The old hospital stood vacant for nearly two decades. Preservationists feared the building would be demolished, but Hyatt Hotels transformed it into luxury lodgings, saving a Route 66 landmark. Throughout this journey, the medical facilities were a boon to businesses along Route 66, supplying them with customers and patients. For instance, an Italian-American family from Tri-Taylor opened Lulu’s Hot Dogs in 1968, replacing a former Sinclair gas station situated across the street from “County.” Today, Lulu’s endures as a cherished spot that serves locals and nostalgic travelers alike.
Open to those with limited financial means, Cook County Hospital, known simply as “County,” would become one of the world’s busiest charity hospitals, eventually treating an estimated 83,000 patients a year during the 1950s. Ambulances carrying patients from all over the city would speed down the well-paved roads of Route 66 to reach “County.”
Cook County Hospital was one of the most recognizable, architecturally distinguished structures on Chicago’s stretch of Route 66. As the years passed, this hospital also became the anchor of the 560-acre Illinois Medical Center District, the nation’s largest concentration of hospitals and research institutions. Established by the 62nd Illinois General Assembly in 1941, the medical district originally included the University of Illinois General Hospital, Cook County School of Nursing, Cook County Hospital, Presbyterian Hospital, Rush Medical College, and Loyola Medical School. The West Side Veterans Administration Hospital, now known as the Jesse Brown VA Medical Center, was later added in 1953.
In 2002, “County” closed and was replaced by John H. Stroger Hospital, one of many modern institutions in the now-thriving IL Medical Center District. The old hospital stood vacant for nearly two decades. Preservationists feared the building would be demolished, but Hyatt Hotels transformed it into luxury lodgings, saving a Route 66 landmark. Throughout this journey, the medical facilities were a boon to businesses along Route 66, supplying them with customers and patients. For instance, an Italian-American family from Tri-Taylor opened Lulu’s Hot Dogs in 1968, replacing a former Sinclair gas station situated across the street from “County.” Today, Lulu’s endures as a cherished spot that serves locals and nostalgic travelers alike.
In the 1950s and ’60s, a thriving automotive scene unfolded along Ogden Avenue