Explore Chicago’s skyline, architecture, and colorful past — from skyscrapers to the Mafia Trail — in Trailokya Jena’s Journey Across the Americas

Trailokya Jena

Chicago, architecture, Willis Tower, Sears Tower, Saint Regis Chicago, Jeanne Gang, Trump Hotel, Chicago Mafia, Al Capone, Mafia Trail, Chicago skyline, Chicago tourism, Trailokya Jena, Journey Across the Americas, Chicago blues, Chicago history, travel writing, iconic buildings

From the gothic and neoclassical designs of the two iconic buildings just mentioned, architects went on to build taller and taller modernist structures with use of steel and glass in geometric proportion that culminated in the construction of world’s tallest building in 1974, the Sears Tower now known as Willis Tower. It remained the tallest globally till 1998 when it lost the title to the Petronas Towers of Kuala Lumpur.

But the bland symmetry of modernist buildings became too similar to the eyes as one skyscraper was hardly distinguishable from the other save for the color and shade of the glasses. This gave way to the post-modernist architectural revolution in skyscraper building and Chicago pioneered the movement in many ways. Woman architect, Jeanne Gang, founder of Studio Gang, currently holds the record for the tallest building built by a woman, The Saint Regis Chicago surpassing her earlier building, the Aqua.

There is a very interesting boat tour for tourists in the city known as the Architecture Tour where you travel sitting on the deck of sleek boats to sail through the canals and river of the city close to the iconic buildings on both sides. Eventually you come out into the Lake to get a great view of the city’s breathtaking skyline.

I never miss this tour whenever I go to Chicago. With each trip I come to see some stunning addition to its skyline, as in this trip I was thrilled to see Gang’s heavenly Saint Regis. I also saw certain alterations to the loud and gross Trump Hotel on the river which was done in a desperate attempt to seize the ‘tallest in the city’ title from Willis Tower.

Whatever may be the background, the architecture of Chicago is pioneering and unique. Each of its famous skyscraper has an identity and brings a special character in play, unlike in New York where only a handful display distinct character. Later I shall post photos of the buildings with brief descriptions to explain the character and significance of the structures.

Chicago has a short but vigorous history compared to its peers in America. Traditionally it is regarded as the city that has given second chance to many Americans, traders, entrepreneurs, industrialists, bankers, property developers, creative artists and even shady characters including cons, bootleggers, fraudsters, violent criminals and failures of all shades and hues elsewhere.

Its past is intrinsically linked with the mafia and their bootlegging enterprise during the prohibition era of 1920s. Al Capone is a prominent name attached to the city. In fact, there is a very popular tour in the city known as the Mafia Trail. A major highlight of the tour is the St. Valentine’s Day Massacre site, a common stop on many Chicago Mafia tours to highlight the location where the 1929 murder of seven men occurred, a significant event in the history of organized crime led by Al Capone.

Then the Chicago Night Tour that introduces you to true crimes after dark. True to its legend, Chicago offered a second chance to Brooklyn born Al Capone who moved there from New York. On the other side, Richard Sears moved in from Minnesota where he was a mere rail road agent to make it big in Chicago.

If you visit the Willis Tower, you’d see display of famous personalities who originated or have lived in Chicago to significantly advance their careers. Those include Opra Winfrey, Michael Jordan, Harrison Ford, Barrack Obama, Robin Williams, Jesse Jackson, Walt Disney, Hugh Hefner, Michelle Obama and even Hilary Clinton was born here.

One of my favorite writers, Saul Bellow belongs to Chicago along with the hugely influential film critic Roger Ebert. Ernest Hemingway lived in the city for more than his 20 initial years. Saul Alinsky and Milton Friedman belong to this city. I had last visited Sears Towers fifteen years ago and don’t remember many names whose association with Chicago got displayed there. But as a Blues and Jazz follower I know some famous exponents from the city including Muddy Waters, Buddy Guy, Willie Dixon, and Benny Goodman lived there. I shall dwell on their art and craft in subsequent parts for their music flew upstream on Mississippi from New Orleans to the north in history.

(Born in Cuttack, the author is a historian, traveler, and a former Income-Tax Commissioner)

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