From its growing skyline to its ever-evolving economy, Chicago looks very different today than it did decades ago.
Chicago is almost unrecognizable from the city it was back in the late 19th and early 20th centuries — in more ways than one.
For starters, the city was quite literally reshaped after the Great Chicago Fire of 1871 left much of the metropolis in charred ruins. Beyond that, though, the Windy City has undergone some significant political and cultural changes, especially during the latter half of the 20th century.
What was once a largely corrupt, mob-controlled gangland reliant on inhumane, unsanitary meatpacking facilities has blossomed into a diverse economy that prioritizes finance, technology, corporate business, trade, higher education, and tourism. While some corruption remains today, Chicago has more than proven that it can reinvent itself time and time again.
That’s not to say there was nothing to love about Chicago back in the old days, either. As an industrial hub, the city was crucial for American development. Architecturally, Chicago laid out much of the blueprint of what a modern American city could look like. Prolific writers and artists like Gwendolyn Brooks, Richard Wright, Archibald Motley, and Margaret Burroughs have greatly influenced the city’s rich and vibrant culture — and The Second City has become tremendously important for the comedy world.
Through our gallery of historical Chicago colorizations below, see how the Windy City established and re-established itself over the years.
Though Holmes is widely believed to have been America's first serial killer, some have argued that his crimes were committed out of desperation rather than passion, as he tried to cover up his many frauds and forgeries.Public Domain
Chicago was just one city impacted by these riots, which involved white mobs attacking Black communities across some 25 cities in the United States. These incidents were fueled by racism as well as national paranoia about communism.Chicago History Museum
This incident would later popularize the phrase, "The whole world is watching," which the demonstrators chanted.Charles H. Phillips/The LIFE Picture Collection/Getty Images
Colosimo was fatally shot at a restaurant, possibly on the orders of his own nephew Johnny Torrio. Their relationship had allegedly devolved after several disagreements, including Colosimo's reluctance to dive into the bootlegging business during Prohibition.The Mob Museum
King later said of the experience, “I’ve been in many demonstrations all across the South, but I can say that I have never seen, even in Mississippi and Alabama, mobs as hostile and as hate-filled as I’m seeing in Chicago.”Public Domain
Though police initially claimed he was killed after firing on them during a shootout, the evidence supported the Panthers' claim that it was a murder.Public Domain
Despite his convictions, many people later believed that the investigations into the murders were mishandled and Heirens was actually innocent.Bettmann/Getty Images
They were both sentenced to life in prison, plus 99 years. Loeb was eventually killed in prison by a fellow inmate, but Leopold was released on parole in 1958 due to good behavior.Chicago History Museum
The Great Chicago Fire Literally Reshaped The Windy City
By early October 1871, a long drought had turned Chicago into a tinderbox of wooden buildings and dried-out sidewalks. Things took a sharp turn for the worse, however, on the night of October 8th, when a fire erupted in the O'Leary family's barn, located on their property at DeKoven Street.
The Great Chicago Fire, as it came to be known, was one of the most devastating urban disasters in American history. Burning for approximately 36 hours, the fire consumed over 2,100 acres of the metropolis, killing about 300 people and destroying some 17,450 buildings.
The fire's true origins remain debated. While it definitely started in or near the O'Leary family's barn, the popular legend that a cow kicked over a lantern and ignited the blaze was later admitted to be fabricated by Chicago Republican reporter Michael Ahern. Other theories suggest it may have started from another incident with a lantern, perhaps a thief knocking it over, or some other kind of teenage mischief, but no one knows for sure.
Public DomainThe aftermath of the Great Chicago Fire in 1871.
Several factors contributed to the fire's catastrophic spread. Chicago had experienced an unusually dry summer and fall, with minimal rainfall for months leading up to the disaster. The city was also largely constructed of wood at that point. Strong southwesterly winds caused the fire to spread quickly, and this also paved the way for convection spirals, or "fire devils."
To make matters worse, the city's fire department was already exhausted from battling earlier fires, and confusion about the new fire's location delayed the response. As the flames advanced, they essentially created their own weather system, generating fire whirlwinds that made firefighting efforts largely futile. The fire devastated the city's downtown business district, consumed the Waterworks building, and destroyed entire neighborhoods.
About 300 people were killed during the fire — a number that could have been far higher if the fire had moved faster. Fortunately, many quickly realized that disaster was imminent, giving them time to escape.
The catastrophe proved to be a transformative moment for Chicago. Like a phoenix rising from its ashes, the city rebuilt using more fire-resistant materials like stone and steel, implemented stricter building codes, and expanded the fire department. The rebuilding effort eventually attracted architects from all over who helped create the modern Chicago skyline.
How The Mob Changed 20th-Century Chicago
During the Roaring Twenties, Chicago became a key center for America's criminal underworld. Prohibition, intended to wipe alcohol from the streets, instead turned the city into a gold mine for gangsters. Thanks to the city's railroad networks, closeness to Canada, and a political system dripping with corruption, Chicago became the perfect staging ground for organized crime.
At one point, the city was home to an estimated 10,000 speakeasies. Behind their hidden doors, liquor flowed, and the criminals who owned these joints used the venues — and the wealth they gained from them — to garner great power and influence, building underground empires.
The most infamous organized crime figure of them all was Al Capone. More than a mere street-tough gangster, Capone operated his empire almost like a corporation, complete with breweries, brothels, gambling houses, and speakeasies. At his peak, he employed more than 1,000 people and earned a fortune that was worth an estimated $100 million — roughly $1.5 billion in today's dollars. Capone balanced brutality with public relations, running a soup kitchen and courting the press to soften his image.
Pix Inc./The LIFE Picture Collection/Getty ImagesGangster Al Capone and his son at a Cubs-White Sox baseball game in 1931.
But Capone was not without rivals.
The North Side Gang, first led by Dean O'Banion and later Bugs Moran, waged open war for control of Chicago's rackets. The feud turned bloody fast, filling newspapers with lurid headlines about horrific crime scenes.
The violence reached its most infamous point on Feb. 14, 1929, with the St. Valentine's Day Massacre. That day, seven members of the North Side Gang were lined up against a warehouse wall and gunned down in a methodical execution that horrified the nation. The main suspect was Al Capone.
Chicago History MuseumThe bloody carnage of the St. Valentine's Day Massacre.
This era was more than just gun battles and gangland funerals, though. The mob's grip on local politics was strong, with officials, police officers, and judges often bought off to keep the machine running. Corruption made Chicago a place where crime could flourish, and it took years of public outrage — and federal intervention — to begin dismantling the syndicates.
The Chicago Black Renaissance
Between the 1930s and the 1950s, Chicago experienced its own version of the Harlem Renaissance. The Chicago Black Renaissance — or the Black Chicago Renaissance — centered on the city's South Side and saw a massive boom in Black literature, artworks, and music.
During this period, Gwendolyn Brooks became one of the movement's most celebrated poets, chronicling the lives of everyday Black Chicagoans with unflinching realism. Her debut poetry collection A Street in Bronzeville garnered national attention, and her next work Annie Allen went on to win her a Pulitzer Prize for Poetry — the first ever awarded to a Black American.
"When you use the term minority or minorities in reference to people, you're telling them that they're less than somebody else."
Another key figure during this time was Richard Wright, who penned the famous novel Native Son, which was set in Chicago and offered a searing portrayal of systemic racism through the story of Bigger Thomas, a young, impoverished Black man imprisoned for two murders.
Wright's memoir Black Boy further solidified him as a powerful chronicler of the Black experience. "I knew that I lived in a country in which the aspirations of Black people were limited, marked-off," he wrote. "Yet I felt that I had to go somewhere and do something to redeem my being alive."
Wikimedia CommonsArchibald Motley's Blues (1929).
Outside the literary world, artist Archibald Motley brought the vibrancy of Black Chicago nightlife to the canvas. His works, such as Nightlife and Blues, captured the energy of clubs and other venues with bold colors and dynamic compositions. Margaret Burroughs' poetry and artwork captured the spirit of the Chicago Black Renaissance in much the same way. When she co-founded the DuSable Museum of African American History in 1961, she gave many of these important works a permanent home.
The Chicago Black Renaissance left a lasting imprint on not just Chicago, but American culture as a whole. Moreover, it blended artistry with activism and helped define the Windy City as a major center for Black cultural production — a legacy that still informs Chicago's art scene to this day.
Next, check out 44 colorized photos that bring the streets of century-old New York City to life. Then, take a look at 36 colorized photos from the early decades of organized crime in America.
