Flappers in front of Belmont Theater
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20 photos of Chicago in the 1920s

Written by:
July 22, 2022
Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

20 photos of Chicago in the 1920s

The 1920s in Chicago were an exciting time. Having almost finished rebuilding after the Great Chicago Fire of 1871 that destroyed 3.5 square miles of the city, the Midwestern metropolis surpassed 3 million residents before the decade was out. In order to house and move all these newcomers, the city undertook massive infrastructure projects, including adopting innovative public transportation options and breaking ground on a number of new construction projects. Dozens of iconic buildings—Wrigley Building, Chicago Daily News Building, and Union Station, among them—were all completed during the decade.

There were also a number of cultural shifts taking place in the city. For starters, tens of thousands of Black Americans moved from the Deep South to Chicago. Their arrival here, inspired by the huge quantity of jobs available, brought about the Chicago Black Renaissance, a creative movement equal in importance to the Harlem Renaissance. Chicago was also home to the first documented gay rights organization in the United States, the Society for Human Rights, founded by German immigrant Henry Gerber in 1924. And of course, there was the rise of organized crime, brought about by prohibition and culminating in the St. Valentine's Day Massacre of 1929.

It's impossible to put into words exactly what life was like in Chicago during the 1920s, so Giggster combed historical archives to compile a collection of photographs that better illustrate the time period. From shots of daily life to important historical moments, these 20 photos exemplify 1920s Chicago.

Elevated view of street traffic
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Schenectady Museum; Hall of Electrical History Foundation/CORBIS/Corbis via Getty Images

Chicago's first traffic lights

As cars became more commonplace in the 1920s, traffic lights became essential in major cities like Chicago, where roads were shared by private automobiles, horse and carriages, and streetcars. Here, traffic flows smoothly on a downtown street thanks to the installation of newfangled electric traffic lights.

Construction workers on steel frame
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Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

The Chicago Daily News building

Two construction workers sit atop the steel frame of the Chicago Daily News building. Completed in 1929, the art deco building was opened by President Herbert Hoover, who pushed the button that started the presses.

Passersby and cars congregate in the front of the Chicago Art Institue
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Bettmann // Getty Images

The Art Institute 'crosses the tracks'

The Art Institute of Chicago first opened in 1879 and immediately became a landmark location for the Windy City. As seen here, the museum was the absolute pinnacle of attention on Michigan Avenue's east side as you move south from the Chicago River. In the '20s, the museum added a major expansion, which bridged the railroad tracks that bordered its east wall, in an effort to house its growing collection. Today, those tracks remain in service and the museum's extension features large windows that allow visitors to see the service traffic below.

Union station interior
4 / 20
Archive Photos // Getty Images

Union Station

Following 10 years of construction, Chicago's Union Station opened in 1925. The third-busiest station in the country to this day, the beaux arts building cost $75 million (or around $1 billion today) to complete.

Crowd gathered at bus stop
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Kirn Vintage Stock/Corbis via Getty Images

CTA Motor Buses

In the 1920s, motor buses were a relatively new addition to Chicago's public transit system—the first motor bus route began in 1917. Here, a group of riders waits at a bus stop on North and Clark Avenues.

People in Grant Park
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Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

The Graf Zeppelin

In 1929, the Graf Zeppelin made the first passenger-carrying flight around the world. During this record-setting journey, the aircraft passed over Chicago, and here, spectators gather on the Grant Park lawn, hoping to get a glimpse of the historic moment.

Flappers in front of Belmont Theater
7 / 20
Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

Liberated ladies

The 1920s, with their looser morals and more relaxed politics, brought new levels of independence for women. Here, two liberated ladies exploit those newfound freedoms by taking their car out for a joyride.

Men dumping wine during prohibition
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Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

Prohibition in Chicago

Prohibition dealt a serious blow to Chicago's economy, as saloon licensing fees had previously accounted for nearly 25% of its overall revenues. Here, a group of men dispose of now-illegal spirits shortly after the law went into effect.

Maxwell street market vendors
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Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

The Maxwell Street Market

The Maxwell Street Market, a precursor to modern-day flea markets, has been a Chicago staple since the 19th century. Above, a group of men (likely all immigrants) stand in front of booths selling all types of wares.

Art museum during snowstorm
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Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

A brutal winter

One of its most brutal winters in recorded history, 1925 brought a jaw-dropping 52.3 inches of snow to the Midwestern city. Here, a horse and carriage attempt to navigate an especially brutal snowstorm.

Open drawbridge on Chicago River
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Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

The DuSable Bridge

A barge passes under the Michigan Avenue Bridge (or the DuSable Bridge). When it was first opened in 1920, the bridge was said to be the only one in the world with two decks, both of which were at highway level.

Men by sign for Bert Kelly’s Stables
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James E. Abbe/ullstein bild via Getty Images

Bert Kelly's Jazz Stables

One of the most popular jazz clubs in Chicago during the 1920s, Bert Kelly's Jazz Stables hosted icons like Joe "King" Oliver and the Dodds Brothers. Its owner, the eponymous Bert Kelly, claimed to have both brought jazz to the city and coined the term jazz himself.

Men at South Water Street Market
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Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

South Water Street Market

Up until the mid-1920s, South Water Street was the primary produce market in the city of Chicago. The buildings that housed the market unloaded produce from riverboats on one side and sold to landlocked customers on the other. In 1925, the city relocated the market to a secondary location (though it kept the name) in order to construct Wacker Drive.

Uptown traffic and pedestrians
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Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

Uptown

In the 1920s, Uptown was one of Chicago's most luxurious neighborhoods. Home to great shopping, theaters, jazz clubs, restaurants, and hotels, the area was where one went to see and be seen (as evidenced by this woman's eye-catching fur jacket).

Louis Armstrong and his orchestra appear onstage at the Sunset Cafe nightclub.
15 / 20
Photoquest // Getty Images

A black and tan club

Louis Armstrong and his orchestra perform at the Sunset Cafe, one of Chicago's famous black and tan establishments. These venues allowed entrance to both Black and white patrons, making them one of the few places in the segregated city where folks of various races could mix.

Police Squad
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Bettmann

The Chicago PD

Organized crime grew exponentially in Chicago during the 1920s and '30s. Groups of Chicago police officers, such as those seen here crammed into one of the force's automobiles, were charged with tracking down these gangsters and putting an end to their nefarious activities.

Chicago skyline
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Chicago History Museum // Getty Images

The Palmolive building

Completed in 1929, the Palmolive Building (which stands in the center of this aerial photograph) served as the headquarters for the Colgate-Palmolive-Peet Company. In the '60s, Playboy took over the lease, and in the early aughts, it was converted to residential apartments.

Lakeside ice from winter storm
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Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

A freezing job

Two men greet a steamship carrying passengers and goods during a winter cold snap. The water intake cribs behind them are completely covered in ice and snow.

Chicago Theater
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Chicago Sun-Times/Chicago Daily News collection/Chicago History Museum // Getty Images

The Chicago Theater

The Chicago Theater, one of the grandest theaters in the country, opened its doors in 1921. Built in a neo-baroque, French Revival style, the movie palace had 3,800 seats and billed itself as "the Wonder Theater of the World."

Summer crowds at Oak Street beach
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Chicago Daily News/Chicago History Museum // Getty Images

A dip in Lake Michigan

In an effort to beat the summer heat, Chicagoans gather on Oak Street Beach to take a dip in Lake Michigan. The second-largest of the Great Lakes, Lake Michigan isn't necessarily warm, but its chilly waters would have provided a welcome respite from the humidity of the Midwestern season.

This story originally appeared on Giggster and was produced and distributed in partnership with Stacker Studio.

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