I love big cities. But I have to admit that I love them in a romantic way only someone who has never actually lived in a big city could love them. Nevertheless, there’s something about the energy of big city life that appeals to me, which may very well be the common experience of glamorizing and wanting what I don’t have. I am, however, especially drawn to their energy, the diversity of the people, the abundance of cultural experiences, and the possibility that the most unpredictable thing could happen at any moment.

As a lifelong resident of Ohio, I love all of our Big Cs: Cleveland, Columbus, and Cincinnati. Each of them are unique and offer a variety of big city-like experiences, but many of the citizens of any of them might describe their home city as a “big small town,” which is in no way meant to be pejorative. By population, Columbus is only the 15th largest city in the U.S. while neither Cleveland or Cincinnati crack the top 50. Therefore, it would be unfair to compare them with the largest of U.S. cities.
With apologies to the many American metropolises which I have either never visited or spent enough time in to form an opinion, when I think of cities, it is New York and Chicago that come to mind for two reasons: 1) with the possible exception of Philadelphia, these are first and second cities of America, and 2) they are the two I have visited often enough to have conjured somewhat-informed appraisals. Therefore, with the caveat that my experience in NYC is limited to Manhattan and my time in Chicago has mostly been spent inside of its various downtown loops, allow me to provide an entirely-subjective analysis of the two cities and to humbly name my preference between the two in regard to the factors that matter most to me.
Pizza. Other than the monstrosities labeled “fruit pizza” or “vegetable pizza,” I’ve yet to encounter a style of pizza I do not enjoy. I am on record as declaring I could eat pizza seven days a week, and should I ever be in a situation as to request a meal that I know will be my last, it will definitely be some variety of pizza. Both New York and Chicago styles of pizza are excellent and served in a such a manner that a single slice of either could be a meal in and of itself. That is if I ever had the willpower to limit myself to just one slice. Chicago style pizza is a true “pizza pie,” thick and stuffed with deliciousness that requires a fork to eat; whereas, the New York style is thin, covered in melted cheese, and dripping in grease. I love them both, but I like to hold my pizza in my hands and for my money, I prefer New York.

Mass Transit. For me, the ease and convenience of NYC’s subway system – only equaled by D.C.’s – is a major point in its favor. Despite warnings to the contrary, I have found the subway cars to be as clean and safe as could ever be fairly expected of a system that daily transports so many people. In fact, on more than one occasion – when I found myself wearing a rube-like expression staring at a ticket station or a wall map of subway lines – a random New Yorker has kindly helped me navigate my way. It’s true that my good Samaritans may have been more motivated by just wanting to get me the f#@* out of their way than by altruistic neighborliness, but either way, they helped get me to where I was going. Yes, the cars can get uncomfortably hot in the summer and super-uncomfortably crowded during any season; whereby, choosing to take a seat will most likely result in trying to avoid staring at or getting too strong of a whiff of the crotches of a multitude of strangers whose nether regions regularly invade your “safe-space” as the trains navigate turns on the tracks or rock back and forth.
As for Chicago’s L trains, mostly because I typically drive to Chicago, I have had far fewer opportunities to ride them. The fact that I pretty much either need a car when in Chicago or to be constantly calling for an Uber or Lyft, is in itself a demerit against it. When I have taken the L trains, I have found them to be less crowded but more confusing to decipher, dirtier, and my fellow riders to be a bit more imposing. With the acknowledgment of a limited experience utilizing Chicago’s mass transit system, I’m declaring a preference for NYC in this category.
Theater. I love theater almost as much as I love pizza. NYC has the largest theater district in the world and a large number of off-Broadway opportunities to view theatrical productions of every ilk imaginable. Therefore, it’s a bit unfair to compare any city’s theater scene with NYC’s. I have attended a number of productions in various Chicago venues and have loved every one of those experiences. Let me add that few people, however, realize that Cleveland actually has the second largest theater district in the United States with ten fully-operational performance spaces. In the theater category, NYC claims the gold, Cleveland the silver, and Chicago the bronze medal.

Running. I make it a point to go for a run in every place I visit. I absolutely love jogging through Central Park alongside other runners, cyclists, rollerbladers, and horse drawn carriages. If I’m not careful, I find myself sightseeing and staring up at the skyscrapers that surround the park in a way that makes me a nuisance to others and a danger to myself. Even still and admittedly somewhat due to my affinity for the Great Lakes, I prefer the run along various stretches of Chicago’s lakeshore to my adventures in Central Park. The view of Chicago’s skyline is breathtaking while Lake Michigan offers its own scenic wonders and provides occasional cooling breezes. I’m going with Chicago on this one.

The People. It’s a bit ridiculous to even attempt to lump millions of people into such simplistic categories as New Yorkers or Chicagoans, so I’m going to declare a draw on this one and simply state what I like about being immersed among each of them. I find New Yorkers fascinating in their gruffness, arrogance, sense of entitlement, toughness, weirdness, and big-heartedness. Chicagoans I like because they are familiar to me as Midwesterners. They possess a kid sibling sense of being overlooked and underappreciated in comparison to NYC and various southern and coastal cities that I can relate to, but they know who they are and apologize to no one for it. If you give it time, a midwestern niceness will almost always eventually seep through their defensive and thick skins.

Although these are surface-level comparisons not based on an overabundance of data or firsthand experience and probably not worth much to anyone, these are my thoughts on comparing New York City with Chicago. Thanks to having family and/or friends in both locations, I hope to visit both with some regularity in the post-pandemic era that awaits.

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