Sunday, March 29, 2026
Evolving Senses in the Windy City
America has always been about its big cities - it could be said that the Manhattan Skyline with Brooklyn Bridge on the foreground is America's most defining image. And while New York City is the most popular scene the World associates with America, it is but one of several impressive cities all around the country, each with their own character and uniqueness. As a resident of the Midwest, nothing embodies America's Big city experience to me better than Chicago.
I first visited Chicago in 2014, still a fresh graduate, working in a manufacturing plant in the northern cheese country. I had not driven much in the USA prior to that visit and was deeply intimidated by the roads per square mile in the city. Highways entering and leaving the city often had 12 lanes. Following driving directions in the early Google Maps was not easy. In many places around the downtown, you not only needed to be on the right road, but the right LEVEL of the road. One wrong exit, and you'd find yourself looping through Lower Wacker and never find a way out of that maze.
Still pinching pockets, the strategy was to find a cheap motel far far away from the Downtown area and take advantage of a unique Chicago institution to get to places: The 'L' - Chicago's vaunted 125-year old (I am not kidding) transit system.
I made more trips in the following decade, seeing that the city was only a short 4 hour drive from metro Detroit where I live. And while Chicago itself has stayed pretty much the same, my senses, sensibilities and experiences have evolved over time. Just like everything else in life, the closer you look at something, the more you see and find interesting. And I believe there are common stages to anyone who gets to know Chicago over a period of time.
The very first trips had been focused on hitting the tourist landmarks. The Bean, the River, the Observation Decks from Tall Buildings, the Chicago-style deep dish Pizza - several boxes to be checked. Along the way, you admired how impressive the skyscrapers were, but without any real feel for what they were.
On the next trip, when you're no longer the most basic Chicago tourist and do not have to cram in all the basic tourist stops, you decide to pay up for the Architecture Tour River Cruise. They tell you the story of the buildings, how the Chicago river was just a large drain for the abattoirs that lined on its shores serving the important Meat Packing Industry, and how the stench and filth forced the City to be built facing the other way for a long period of its history.
And then somehow magically, in the late 19th Century, the City planners decided to invert the flow of the river by connecting it to a nearby tributary of the Mississippi River. Fresh water from Lake Michigan now became the source of the Chicago River instead of the destination of filthy organic matter from the city.
The type of ambitious human intervention that characterized the Industrial Age in America.
In subsequent decades, every site along the upgraded river was built over. The railroad companies that owned the land surrounding the river build a whole second (and third) floor of the city above the tracks and leased them to real estate developers - another innovative American solution to land scarcity. This resulted in the maze of underground levels that had me in a jam during my earlier visits to the city.
By the time you visit the city a handful of times, your mind settles down when confronted with the chaos of the big city. You realize that there is more to Chicago than the tourist destinations. You realize there is a wide array of delightful dining choices when you give up on enjoying the deep-dish Pizza (trying hard not to use the "O" word here). You are content with just being there, walking along the river, among the megaliths.
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