Chicago's amazing secrets revealed in historic photos

Urban legends

Chicago is one of the USA’s greatest urban hubs. But did you know that the world’s first skyscraper was built right here in the city? Or that notorious gangsters such as Al Capone once ran the streets?

We take a deep dive into the Windy City's history to reveal the fascinating story of Chicago.

It forms the traditional homelands of many Indigenous peoples

Long before Euro-American settlers arrived on the land that now encompasses Chicago, Indigenous people had called the region home for time immemorial. A network of waterways proved a lifesource for Native tribes including what is now the Council of the Three Fires, an alliance of the Ojibwe, Odawa and Potawatomi Nations.

Pictured is a portrait of Shabbona, a chief of the Potawatomi tribe, snapped in 1859. 

The first non-Native resident arrives

In the 1770s, the region’s first non-Native settler arrived in the region. His name was Jean Baptiste Point du Sable and he was a free Black man originally from Haiti, who had migrated north from New Orleans. He was also an entrepreneur and a fur trader, and he eventually married a Potawatomi woman named Kitihawa.

The pair had two children and established an estate that included a humble home, a bakehouse and stables.

Fort Dearborn is built

Trade continued to increase in the area and, in 1803, Fort Dearborn was constructed. After settlers colonised the Great Lakes region, tensions increased between the new inhabitants – who brought with them diseases that were deadly to the Natives – and the original inhabitants of the land.

The fort, built on a bend on the Chicago River, was intended as a defensive site.

The Battle of Dearborn is fought in 1812

Fast forward to 1812 and tensions were coming to a head.  The decade-old Fort Dearborn had become unliveable and the garrison were ordered to evacuate by a US Army commander.

However, they were met with a 500-strong army of Indigenous peoples. The Native peoples were victorious in the battle, with the US side suffering a high number of casualties.

The Indian Removal Act is signed

New settlers continued to pour into the Chicago area and the Great Lakes region, further weakening the hold that Indigenous peoples had on their ancestral homelands. Then, in 1830, President Andrew Jackson ultimately signed the Indian Removal Act and the tribes were forced west.

This is a depiction of the Chicago area in the early 1830s.

Chicago is incorporated in 1837

After continued growth through the 1830s, Chicago was finally incorporated as a city in 1837. By this point, the population sat around 4,000 people. Its location – serving as a gateway to the West and to many important waterways – made it an ideal trading hub.

This illustration is an artist's depiction of the area from 1837.

The Illinois and Michigan Canal is built

Further development came with the building of the Illinois and Michigan canal in 1848. The new waterway joined up the city with the headwaters of the mighty Mississippi River, further enhancing Chicago’s role as centre of trade. 

Chicago’s railroads are expanded

However, the need for the canal diminished with the building of the Chicago, Rock Island and Pacific Railroad in 1852. In 1854, it became the first Chicago railway to cross over the Mississippi River.

The Great Fire of Chicago ravages the city

The year 1871 will always be a blight on Chicago’s history. Given the city’s rapid growth and congestion, fires were becoming more frequent, but none matched the total devastation of the October 1871 blaze.

It began in a street barn on the West Side, tearing through the city’s wooden buildings, after a summer with barely any rain had left Chicago parched.

Chicago builds back

Devastatingly, some 300 people were killed in the blaze and many hundreds more were left homeless. The Business District was destroyed, though the stockyards remained mostly intact.

However, Chicago did not spend too long in the dirt. The effort to restore the city was termed ‘the Great Rebuilding’, with new structures made in stone, brick and marble.

Chicago hosts the World Columbian Exposition of 1893

Just over two decades later, Chicago was fighting fit once more. And in 1893, the city was the host of the World’s Columbian Exposition, which was intended to commemorate the 400-year anniversary of Christopher Columbus’s voyage to America.

Chicago gets the world’s first skyscraper

Chicago is often held up as the home of the world’s very first skyscraper. The Home Insurance building was finished in 1885, soaring to a then-towering 138 feet (42m) and 10 storeys.

The building’s pioneering architect was Major William LeBaron Jenney, who has become known as the “Father of the American skyscraper”. 

The Chicago Cubs were born in 1903

At their earliest beginnings, Chicago’s famous baseball team was known as the White Stockings, and they were a founding team of the National League back in 1876. They became the Cubs in 1903 and since 1916 they’ve called Wrigley Field – the second-oldest ballpark in the league – home.

Chicago is thriving at the turn of the century

Chicago was buzzing at the turn of the century. The population was exploding as immigration from Europe and the South continued, and the streets were filled with carts and early automobiles.

Notice the glittering Majestic Theater in this photo – it was opened in 1906 and is now the CIBC Theater.

The Great Migration

The Great Migration refers to the movement of African-Americans from the American South to cities in the north. Some half a million African-Americans settled in the Windy City from around 1916 up to the 1970s, making Chicago a hotbed for jazz music.

Pictured here in 1915 is the Morris family, one of the many African-American families who made the journey.

Chicago is rocked by the First World War

The First World War affected the USA in its entirety and the Windy City played its part. Now a beloved tourist attraction, Navy Pier served as a military training base, while the city used its industrial might to produce everything from aircraft to rations.

Prohibition takes hold in the city

In the early 1900s, the city of Chicago made a tidy part of its revenue from brewing beer, but Prohibition stopped the industry in its tracks. Temperance was enforced from 1919 and this photo shows beer being dumped into Lake Michigan.

Gangsters take hold of the city

As Prohibition took hold, Chicago became a hotbed for gangster culture and the city’s illegal underworld thrived. There was no mobster more notorious than Al Capone, who ran thick gambling and bootlegging rings across the city.

Capone is pictured here exiting a hotel sometime in the 1920s.

Gangsters take hold of the city

Chicago gangsters shared fierce rivalries through the 1920s and 1930s and perhaps no conflict was stronger than that between Capone and Earl “Hymie” Weiss, leader of the North Side gang. In this photograph, crowds gathered at the site where Weiss was murdered by Capone’s mob.

Al Capone helps out during the Depression

But for all the bloodshed, Capone apparently had a benevolent side too. The Great Depression had cities across the US including Chicago in its grip throughout the 1930s and many families suffered poverty.

This photograph shows a soup kitchen organised by Capone, who was also finally sentenced in the early 1930s.

The Mother Road is built

Today Chicago is famously the start of Route 66, which was built in 1926. The new roadway joined up many existing state and national routes and wended its way 2,400 miles (3,863km) towards Santa Monica, California.

Much of the historic route is still drivable today and you can find the pictured sign in the Windy City. 

Chicago is a hub for jazz and blues

The Great Migration continued through the mid century and Chicago gained a reputation for being a cradle of jazz and blues. Snug jazz and blues joints sprung up across the city and Chicago-based record labels gained national recognition.

Chicago holds another World’s Fair

Chicago’s second World’s Fair was intended to celebrate “a century of progress”. The keenly attended event showcased everything from Art Deco buildings to new-fangled motor cars and was intended to be a rebuttal of the Great Depression, which still had a hold over the USA at this time.

The US enters the Second World War

The US entered the Second World War in 1941, after a surprise attack by Japan on Hawaii’s Pearl Harbor, and Chicago once again aided with the war effort. The Great Lakes Naval Training Station, immediately north of Chicago was extremely important, while Chicagoan factory workers turned out vital goods including military electronics.

Here citizens line up on Chicago’s streets to receive their rations.

Deep dish pizza is invented

No trip to the Windy City is complete without a belly-busting deep dish pizza feast and one parlour in particular claims to have invented this Chicagoan treat. It was apparently pioneered by entrepreneurs Ike Sewell and Ric Riccardo, who opened the Near North Side’s Pizzeria Uno in 1943.

Second City comedy troupe is born

Today Chicago is well known for its improv comedy scene and Second City, a troupe begun in 1959, is considered to be the place that it all began. Comedy heavyweights such as Tina Fey and Amy Poehler all have ties to Second City and you can still catch a show today.

Willis Tower opens

Like all of America’s major cities, Chicago’s skyline is ever changing and that was true back in the 20th century too. One of the most iconic additions was the Willis Tower, which was opened back in 1973.

Upon its completion, it was the tallest building in the world and it still remains one of the highest buildings in the world today. 

The city is ravaged by the Chicago Blizzard of 1979

Chicago is no stranger to bracing weather, suffering freezing winters with often multiple feet of snow. However, the Chicago Blizzard of 1979 has gone down in history.

More than 21 inches of snow fell over two days with large swathes of northern Illinois grinding to a halt. Public transit was largely shut down and this photo shows abandoned cars in a city street.

Millennium Park opens in 2004

Today Millennium Park is one of Chicago’s major draws, pulling in a whopping 25 million visitors each year. But it’s actually a lot newer than you might think.

With ground breaking in the late Nineties, the park wasn’t finished until 2004. The famous stainless steel sculpture, Cloud Gate, better known as simply “the Bean” was the vision of Anish Kapoor and was finished two years later, in 2006.

The Windy City today

Today some 2.7 million residents call Chicago home and it’s the third largest city in the US (behind New York City and Los Angeles). The city saw a whopping 48.9 million visitors pour into the city in 2022 too.

They come for long-standing attractions such as Millennium Park and the Willis Tower, as well as a stellar theatre scene, urban beaches and world food in the city’s 77 neighbourhoods. 

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