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25 Vintage Photos Of Chicago Back In The Day

Two images of Chicago.

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Published June 12, 2025

Published June 12, 2025

As decades pass, things change in pretty drastic ways. There isn't much left out there that looks the same as it did even just 10 years ago. Due to new technology, a growing population, and changing trends, cities in the past look almost unrecognizable when compared to modern times. Traffic, crowds, and big billboards are just some of the new developments in cities as years fly by.

Chicago is a major city in Illinois. Chicago is known for many things, including its cuisine. From deep-dish pizzas to Chicago-style hot dogs, beef sandwiches and much more, people are eating well in Chicago. The city also has a rich history in jazz and blues music, as well as a strong sports culture. A lot of things happen in Chicago, but it has changed a lot over time.

Here, we have collected 23 vintage and historical images of what Chicago looked like in the past. These images are all from the 1950s, so things looked quite different. It's cool to see how just one part of the world has been affected by change and development throughout the decades.

A man and his son in Chicago, 1927

(Source: Redd)

The transition from trolley to bus, Chicago, 1948

(Source: Redd)

North side of West Chicago avenue, 1970

(Source: Redd)

City parking in Chicago, 1932

(Source: Redd)

A family home and car, 1908

(Source: Redd)

Chicago, 1895

(Source: Redd)

Dearborn and Randolph streets, Chicago, 1900

(Source: Redd)

ChicagoFest, 1981

(Source: Redd)

At the water pump, 1899

(Source: Redd)

Kids in Chicago, 1910

(Source: Redd)

Out on the town, Chicago, 1950s

(Source: Redd)

Waiting for the bus, Chicago, 1925

(Source: Redd)

Two boys in Chicago, 1941

(Source: Redd)

Sears in Chicago, 1957

(Source: Redd)

Lining up to go to the movies, Chicago, 1941

(Source: Redd)

South Side Chicago, 1941

(Source: Redd)

Michigan Avenue, Chicago, 1938

(Source: Redd)

Oak Street Beach, Chicago, 1936

(Source: Redd)

Regal movie theatre, Chicago, 1941

(Source: Redd)

A couple at a rollerskating rink, 1941

(Source: Redd)

A dust storm hits, Chicago, 1934

(Source: Redd)

Maxwell Street Market, Chicago, 1957

(Source: Redd)

Traffic on Michigan Avenue, Chicago, 1927

(Source: Redd)

An accident in Chicago, 1960

(Source: Redd)

Outside the theatre, Chicago, 1940s

(Source: Redd)

Tags: history, nostalgia, nostalgic images, chicago, illinois, chicago in the past, chicago history, boomers, baby boomers, cities in the past, chicago illinois, illinois in the past, chicago photos,



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