Route 66 is the ultimate American road trip — and it all starts in Chicago. Known as “The Mother Road” and “The Main Street of America,” this iconic route stretches more than 2,400 miles and has connected travelers from the Great Lakes to the Pacific Coast for almost 100 years. Learn how to experience Route 66 in Chicago and how the road has shaped the stories of the many Chicago communities it touches.
In the 1920s, America became an automobile nation. At the start of the decade, there were 8 million cars on the road, but roughly 32,000 of the nation’s 2.5 million miles of rural roads were paved, making transcontinental travel prohibitively slow. By the end of the 1920s, Americans owned 23 million cars, with many driving Henry Ford’s affordable Model T.
More cars meant more demand for paved roads. In 1921, Congress passed the Federal Aid Highway Act, which called for a network of roads covering the entire country. A few years later, plans for interstate routes were approved for all 48 states. Route 66 stretched more than 2,400 miles from Chicago to Santa Monica, California. Cy Avery, the Oklahoma highway commissioner known as the “Father of Route 66,” dubbed it “The Main Street of America.” This route was considered the primary path between the Great Lakes and the Pacific Coast. Route 66 was officially established in 1926. The Illinois stretch of Route 66 began as a two-lane road known as SBI4, which followed the route of the old Pontiac Trail from Chicago to St. Louis. At first, SBI4 began in Cicero, but its designation as Route 66 increased traffic. To accommodate this, the starting point was moved to Michigan Avenue and Jackson Boulevard in Chicago. Ogden Avenue has traditionally been a major transportation route into and out of Chicago. This street parallels both the south branch of the Chicago River, which was once the main waterway toward the Mississippi, and the Chicago, Burlington & Quincy railroad tracks. The Route 66 era was the heyday of Ogden Avenue and the neighborhoods it runs through. Route 66 was and still is an emblem of the nation’s car culture. From the 1920s through the 1950s, dozens of repair garages, tire suppliers, and automobile dealers set up shop along the street. The development of the interstate highway system, the result of a bill signed by President Dwight D. Eisenhower, led to the decommissioning of Route 66 and the demise of many of Chicago’s Ogden Avenue businesses. Drivers were offered a faster course to the southwest suburbs and central Illinois. In the 1960s, construction began on Interstate 55, and in 1977 the “End of Route 66” signs on Jackson Boulevard came down. A few remaining restaurants and repair shops along Ogden Avenue still display Route 66 memorabilia, ensuring its years as a piece of America’s most mythologized highway are never forgotten.
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.
In the 1950s and ’60s, a thriving automotive scene unfolded along Ogden Avenue in North Lawndale, directly influenced by Route 66. As American car culture started to embrace fashion and personalized design, Ogden Avenue became one of Chicago’s busiest automobile rows, filled with car dealerships and repair shops.
Ben Geller Chevrolet, with its iconic red-and-blue neon sign, glowed for nighttime car buyers, who could marvel at the latest models displayed behind a plate glass window. Sid Luckman, the Bears’ Hall of Fame quarterback, even owned a Chrysler/Plymouth dealership on this strip. Among the landmarks that are still standing, Louis Ehrenberger’s Castle Car Wash, a gas station and garage with a crenellated turret, has become a popular site on Route 66. Its years of operation, from the 1920s to the 1970s, paralleled the highway’s peak timeframe. For most of the Route 66 era, North Lawndale was a predominantly Jewish neighborhood with many residents speaking Russian. By around 1945, it was estimated that about 65,000 Jewish people lived in this neighborhood. This vibrant area fostered important community institutions including synagogues, an orphanage, a home for the aged, and Mount Sinai Hospital, which is still in operation. However, North Lawndale witnessed a significant shift in the 1960s as transportation planners diverted traffic from Route 66 to the Congress Expressway, and then to Interstate 55. This transformative development helped contribute to a gradual population decline after the neighborhood reached its peak population in 1960, with 124,937 residents. Many of the automotive businesses also closed since there were fewer visitors driving on the former Route 66 road. The buildings they left behind are now occupied by a handful of mom-and-pop car parts dealers and repair shops, many of which celebrate their Route 66 roots.
The large park in this neighborhood predated Ogden Avenue, formerly known as Route 66, but its layout was adjusted to accommodate the roadway that ran through it. Opened in 1879, it was one of three West Side parks, along with Humboldt and Garfield Parks, designed by architect William Le Baron Jenney.
The park was originally named for Illinois Senator Stephen A. Douglas, an early advocate of transcontinental travel whose ambition of building a railroad from Chicago to the Pacific Ocean resonated with the fundamental goal of Route 66. In 2020, after an advocacy effort by neighborhood residents, the Park District voted to change the name from Douglas Park to Douglass Park for abolitionist Frederick Douglass. In the mid-1900s, Jens Jensen was hired as general superintendent of the West Side Park system. Along with Frank Lloyd Wright, Jensen was a pioneer in Prairie-style landscape architecture, a late 19th- and early 20th-century movement drawing inspiration from the flat, bare landscape of the American Midwest. After Ogden Avenue was built through the park, Jensen planted a garden with perennial beds and a lily pool on the south side of the street. This acted as a buffer between the traffic and the playing fields. At the garden’s entrance, Jensen built Flower Hall, whose grand arch was surrounded by breezeways supported by multiple columns. In 1928, shortly after Ogden Ave became Route 66, the Chicago Park District Commission built a fieldhouse to accommodate the increased traffic and visitors through the park. This classical structure, which contains a terrazzo-floored ballroom, was the work of architects Christian S. Michaelsen and Sigurd A. Rognstad. Bisected by Route 66, Douglass Park was considered an important attraction along the highway, with the Park Commission laying out a road network tailored to motorists. The park was located between two other important recreational institutions along the route, the Ogden Theatre, a motion picture palace, and the Douglass Park Auditorium, where Yiddish plays were performed until 1951 for visitors and travelers. In 2000, Douglass Park’s connection to Route 66 was commemorated with a mural that included a map of the park and city landmarks such as the Art Institute of Chicago’s iconic lions.
In the early 1900s, the Hawthorne Works of Western Electric began as a few dozen buildings clustered on a muddy prairie just outside city limits in Cicero, IL. It quickly grew into one of Chicago’s largest industrial complexes and employers. This company was best known for manufacturing home telephones and operators’ switchboards.
By 1929, more than 40,000 men and women reported to work at the massive 141-acre campus and used Route 66 to get there and transport goods. During World War II, Hawthorne contributed to the war effort by producing flight trainers, submarine detectors, mine fuses, and and radios for planes, tanks, and artillery. Route 66 served as a valuable path for the transportation of wartime equipment. While optimal for the development of weaponry, Hawthorne’s early 20th-century buildings were ill-suited for the temperature and humidity controls required to produce modern electronic switching equipment. In its later years, the business pivoted and started forging copper rods that were twisted into telephone wires. In the mid-1980’s, Hawthorne Works reached its end and closed its doors with only 1,100 employees remaining. The presence of Route 66 left a significant mark in Little Village especially since it brought so much traffic in the surrounding area that engineers built a viaduct so cars could pass over Cicero Avenue and the Chicago, Burlington & Quincy (CB&Q) railroad tracks in the late 1930’s. At the time, this was “the most complicated grade separation ever tackled by the Illinois highway department.” Hawthorne Works and Route 66 collectively contributed to Little Village’s growth, as industrial workers sought inexpensive housing accessible to their jobs and local businesses benefited from the large influx of travelers. The neighborhood was settled first by a Czechoslovakian and Polish immigrant community, and later Mexican immigrants moved here in the 1960s.
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