Chicago, Illinois – The Route 66 Journey Begins
Chicago, Illinois, a vibrant metropolis nestled on the shores of Lake Michigan, serves as the symbolic starting point for the iconic Route 66. As the third-largest city in the United States, Chicago boasts a rich and complex history, a story etched into its architecture, its neighborhoods, and the very spirit of its people. While urban development has obscured many vestiges of the Mother Road’s golden era, Chicago still offers glimpses into its past, particularly along the city’s periphery and within its downtown core, where historic buildings stand as testaments to the city’s enduring legacy and the legendary highway’s origin. This article explores the fascinating history of Chicago, Illinois – The Route 66 Journey Begins.
The narrative of Chicago begins long before the rumble of engines on Route 66. The first known settler in the area was Jean Baptiste Point du Sable, a resourceful African American man hailing from Santo Domingo. In 1781, Du Sable recognized the strategic advantages of the location at the mouth of the Chicago River, establishing a trading post that would become the nucleus of the future city. The area’s importance was further solidified in 1802 with the construction of Fort Dearborn, a military outpost that, for years, faced intermittent attacks from various Native American tribes until Chief Black Hawk’s defeat in 1832. A year later, in 1833, Chicago was officially incorporated as a town, a small but promising settlement that, by 1837, already boasted a population of over 4,000 residents.
The year 1848 marked a turning point in Chicago’s trajectory. The arrival of the first railroad line ignited an unprecedented boom, transforming the town into a burgeoning transportation hub. By 1860, a mere twelve years later, Chicago was interwoven with a network of a dozen railroad lines, serving as a central connection point for goods and people across the nation. This explosive growth fueled a dramatic population surge, with the city’s inhabitants exceeding 100,000. The subsequent decade witnessed even more rapid expansion, with the population tripling and Chicago, Illinois – The Route 66 Journey Begins solidifying its position as a major urban center poised for national prominence.
However, the city’s relentless growth faced a devastating setback in 1871. The Great Chicago Fire, a cataclysmic event that began on October 8th and raged for two days, consumed a vast swathe of the city. The inferno engulfed 3.5 square miles, reducing 17,450 buildings to ashes and claiming the lives of an estimated 300 people. Despite the widespread devastation, Chicago displayed remarkable resilience. Just six weeks after the fire, construction commenced on over 300 new buildings, signaling the city’s determination to rebuild and emerge stronger than before. This devastating event did not stop Chicago, Illinois – The Route 66 Journey Begins.
The late 19th century witnessed further innovations and advancements that shaped Chicago’s identity. In 1891, the city unveiled its first elevated railway, known as "The El," a groundbreaking transportation system designed to alleviate congestion and improve accessibility. The El’s circular route around the downtown area quickly earned it the moniker "The Loop," a name that persists to this day. While the engines have evolved significantly since the 19th century, the El and the Loop continue to serve as vital components of Chicago’s public transportation network, carrying countless commuters daily.
That same year, Chicago witnessed the construction of its first skyscraper, the 16-story Monadnock Building, located at 53 W. Jackson Boulevard. This architectural marvel represented a bold step forward in urban development, showcasing Chicago’s ambition and its embrace of innovative construction techniques.
In 1893, Chicago hosted the World Columbian Exposition, a grand spectacle commemorating the 400th anniversary of Christopher Columbus’s arrival in America. This ambitious undertaking required an investment of over $27 million and transformed a 633-acre site into a dazzling showcase of art, technology, and culture. From May to October 1893, the fair attracted an astounding 27 million visitors, representing nearly half the population of the United States at the time.
The World Columbian Exposition introduced numerous novelties and innovations to the American public. It served as a launchpad for iconic brands such as Cracker Jacks, Aunt Jemima Syrup, and Pabst Beer, and also introduced the concept of diet soda. The exposition is also credited with popularizing the hamburger and solidifying the concept of the modern carnival. The United States Postal Service issued its first commemorative stamps, and the Mint released its first commemorative coins to mark the event.
Amidst the grandeur and excitement of the exposition, a lasting nickname was bestowed upon Chicago. Charles Dana, the editor of the New York Sun, allegedly coined the term "Windy City" in response to what he perceived as the excessive boasting of Chicagoans about the World’s Columbian Exposition. The nickname stuck, becoming an enduring, and sometimes affectionate, descriptor of the city.
The year 1896 brought a darker chapter to Chicago’s history with the conviction of Herman Mudgett, better known as H.H. Holmes, one of the nation’s first documented serial killers. Holmes, a medical school graduate, embarked on a life of deceit, torture, and murder, primarily targeting young women who had come to Chicago for the World’s Columbian Exposition. He constructed a custom-built "murder castle" at 63rd and Wallace, equipped with gas chambers, incinerators, and other horrific devices designed for the sole purpose of torture and extermination. Holmes was ultimately apprehended and hanged on May 7, 1896, bringing an end to his reign of terror.
Before Route 66 became the legendary highway it is known as today, a well-traveled road connecting Chicago and St. Louis existed: the Pontiac Trail. Recognizing the importance of this route, Illinois began paving the road in 1918, and by the time Route 66 was officially established, the entire stretch was paved. In 1927, Route 66 signs began appearing along the Illinois route, signaling Chicago’s connection to the burgeoning national highway system. During this period, Chicago’s vibrant music scene was taking shape. Louis Armstrong, a member of "King Oliver’s Creole Jazz Band," became a prominent figure in the city, contributing to the rise of the Jazz Age.
The late 1920s in Chicago were marred by escalating gang violence, as rival factions battled for control of the lucrative bootleg liquor trade. The violence reached its peak on February 14, 1929, with the infamous St. Valentine’s Day Massacre. Seven members of George "Bugs" Moran’s gang were brutally murdered in a North Clark Street garage, victims of an ambush orchestrated by rival mobsters. Although law enforcement suspected Al Capone and his gang of being responsible for the massacre, they were never able to secure a conviction.
Al Capone was eventually prosecuted for tax evasion and sentenced to 11 years in prison on October 24, 1931. He was released eight years later, on November 16, 1939, but his health had deteriorated significantly due to the effects of syphilis. He suffered from mental impairment and died on January 25, 1947.
Throughout this tumultuous period, Route 66 continued to attract travelers from all walks of life, seeking adventure and opportunity on the open road. One enduring establishment that catered to these travelers was Lou Mitchell’s Restaurant, located at 565 W Jackson Boulevard. Since 1923, Lou Mitchell’s has been serving up coffee and classic American cuisine, becoming a beloved landmark for both locals and Route 66 travelers. Nearby stands Chicago’s Union Station, once home to a Harvey House Restaurant, offering travelers a taste of fine dining during their journeys. The official starting point of Route 66 is marked at Grant Park on Adams Street, in front of the Art Institute of Chicago, where the "Begin Route 66 Sign" proudly stands.
Following Adams Street west for approximately 2.5 miles, travelers then turned left onto Ogden Avenue, entering a more established part of town. Passing through Douglas Park, one of Chicago’s oldest parks, motorists would have spotted the Castle Car Wash at 3801 W Ogden on their left. Now closed, the car wash primarily serves as a parking lot for the fire station across the street.
The road continues into the suburb of Cicero, once Al Capone’s base of operations. This area contains several Route 66-era buildings, including the Cindy Lyn Motel at 5029 W Ogden and Henry’s Drive-In.
Route 66 snakes through the Chicago suburb of Berwyn, where limited attractions remain. A piece of artwork called the "Spindle," a 40-foot spike topped with nine cars, stood until it was dismantled in May 2008.
The route becomes difficult to follow as signs are rare and two alignments occur as you enter Lyons. With maps, travelers can continue their journey through the towns of McCook and Plainfield toward Romeoville and Joliet.
Chicago, Illinois – The Route 66 Journey Begins is a story of growth, resilience, and enduring spirit. As the starting point of the Mother Road, the city represents the beginning of a journey, both literally and figuratively, into the heart of America.