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Chicago Skyline Photo History

Updated on February 19, 2008

Chicago is home to a lot of famous foods, places, and people. When you think of Chicago, what pops into your head? Chicago has a well-known nickname of the Windy City. It is also renowned for its hot dogs and deep dish pizza. Then, there is Wrigley Field with its classic red sign. You can’t forget about Oprah Winfrey. That’s right, if you ever want to be on her show, just head to Chicago (don’t forget to get tickets first). The city’s skyline is also famous with its collection of skyscrapers.

You know, there are plenty of resources available to learn about the history of Chicago, Illinois. You can find tons of books, websites, and documentaries out there full of interesting information. So, with that in mind, I’m not aiming to present that kind of information here. Who needs a regurgitated history of the Windy City? Instead, let’s watch it grow with our own eyes—through photos. I tried to choose pictures that capture views of the city for each decade of the twentieth century. There are a few gaps, but you will get a general idea of how the city grew.

Chicago gained worldwide notoriety in the 1970s by building the Sears Tower—which held the top spot for highest building in the world for a while. Currently, it is the tallest building in North America and third in the world.

Basically, Chicago is famous for the beautiful buildings that make up its memorable skyline. If you are ever in the Windy City, I insist that you take one of the historical tours—on land or water. It will be completely worth it to experience the history and story the city has to offer. Founded in the 1830s, Chicago is now one of the biggest cities in the United States.

Have fun viewing these pictures – and definitely let me know what you think by leaving a comment in the comment box at the bottom of the page. Enjoy your stroll down this historical, picture lane.

Chicago in 1910

Chicago 1927

Chicago 1930s

Chicago 1940s

Chicago 1952

Chicago 1960s

Chicago 1976

Modern Day Chicago Skyline

Chicago Skyscrapers


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      Ernesto Castro 5 years ago

      The pic labeled "Chicago 1976" is actually from the early 90's, you can tell because 2 Prudential Plaza and the AT&T Center were built in the late 80's early 90's and also because latter additions to the skyline are missing. Just wanted to additionally point out that well before the Sears Tower, Chicago was already known worldwide for its structures.

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      JOE MEDINA 6 years ago


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      Chicago pictures 8 years ago

      You have some nice photos. You might enjoy my <a href="">Chicago skylinephotos</a> which I have been taking for over 30 years now.