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Skyscrapers of Chicago

Chicago is known as the birthplace of the skyscraper as a result of the previous wooden city that burned in the Great Fire of 1871. After the fire, an 1874 bylaw outlawed wooden building construction in the downtown area. As a result, architects had to find other building materials that were not wood.

The nine story Home Insurance Building (1885), is often credited with being the world’s first skyscraper. It was only 138 feet tall but was built with a steel skeleton which meant that the structure could be built higher than any wooden structure. By 1889, Chicago had five more skyscrapers than New York City. The Home Insurance Building was as razed in 1931 and replaced by an even taller building, the 535 ft tall Field Building.

I have always had an interest in seeing and sketching architecture and I wanted to do a pre trip sketch about Chicago’s skyline. I found my inspiration in a Fodor’s travel guide (2019).

The guide laid out some of Chicago’s more iconic buildings in chronological order. It looks like a stock prospectus, as it grows over time, with occasional dips.

A view of Chicago’s skyscrapers from its tallest skyscraper.
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Big John: The John Hancock Center

After I had visited the very touristy Skydeck on the 103 floor of the Sears Tower, I headed north of the river and went to the 93 floor of the less touristy John Hancock Center.

When the building was completed on May 6, 1968, it was the second tallest building after the Empire State Building. It is now the fifth tallest building in Chicago and the thirteenth in the United States.

This building also has a personal twist. A mother of one of the my former students not only grew up in Chicago but grew up on the 62nd floor of the John Hancock Center! She would swim at the world’s highest indoor swimming pool on the 45th floor. For some reason, it never occurred to me that people actually lived in these skyscrapers. I always thought of them as just office towers. The docent on my architecture river cruise noted that Big John was one of the first residential towers ever built.

The John Hancock Center from Michigan Avenue. My neck hurts just looking at this image!

I entered the tower on the Michigan Avenue side and secured a ticket to the 93 floor. The elevator was not as pacy as the Sears Tower but I arrived at 360 Chicago in due time.

The view from the 93 floor was astonishing. Partly because it seems like you are right on the shore of one of the Great Lakes, Lake Michigan. You can walk around the 93 floor and have views from all the cardinal points of the compass. But first I needed a sketching seat and a drink.

Looking down from the east side of the tower.

I found both at the Cloud Bar on the northern facing part of the tower. Here you certainly pay for the view. At elevation, drinks on my flight to Chicago where cheaper!

I took my bubbling concoction to a table and sketched the shoreline below me and the skyscrapers to my left. Out on the lake where sailboats and motor craft and a steady stream of traffic heading north on Lake Shore Drive.

$21 for Windex in a glass. It was smoking and bubbling like something in Doctor Frankenstein’s lab. But it was delicious!
My Cloud Bar sketch from the 93rd floor. From the view looking north. I chose to only paint in Lake Michigan.
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Skyscrapers of Chicago From the River

The Great Chicago Fire of 1871 started it all.

The city had to first burn down before it could build up. And up and up.

Before the fire of 1871, the city of Chicago was a city of wood. When the city was rebuilt, wooden buildings where banned in downtown by bylaws. Architects had to find other building materials and they chose steel!

A great way to see Chicago’s architecture, especially the skyscrapers, is from the Chicago River. And the best way to do that is to take an architectural boat cruise.

Cruises are offered by many companies but the best are run by the Chicago Architecture Center, so I boarded Chicago’s First Lady at 3:15 and sketched the scene before we departed (featured sketch).

Each cruise has a volunteer docent that gives history and insight into the towering buildings the boat passes under. Our docent, Mike, was especially interested in my sketches. I feel the best way to understand architecture (or anything else really), is to sketch it. I planned to do some quick sketches on the tour but I was too engrossed with the architecture and history to open a sketchbook and make that pen dance.

What follows are some photos from the cruise.

The twin 61 story residential towers of Marina City (1967).
A Chicago Art Deco masterpiece the Union Carbide and Carbon Building (1929). It is said that the top of this build was designed to look like a Champagne bottle. You be the judge.
Another Art Deco masterpiece: the Merchandise Mart (1930).
One of Chicago’s newest skyscrapers: the St. Regis tower, at 1,198 feet is the third tallest skyscraper in Chicago. The 101 story tower was completed in 2020. It was designed by Jeanne Gang making it the tallest building in the world designed by a woman.