my three favorite things about chicago

I know many, many people from Chicago. But I have never lived there. I don’t follow any Chicago sports teams nor read news about Chicago. There are millions of people more qualified to write about it. Nevertheless, I will take up the unsolicited mantle as spokesperson for the city. I have been to Chicago several times. My sister lives there. I have aunts and uncles who lived there. Many friends are from there. The Broncos and Bears often swap mediocre players and coaches. I feel a strong connection there. The city is young and fun and has plenty to do and see. I could recount every visit I’ve had in detail. But instead I think I’ll use my anecdotal and unqualified perspective take a complex and storied city and boil it down to three general terms. Because who doesn’t love a list?

1. The Architecture

I’m not going to research anything for this, just using fallible memories and old photographs. No city comes close to having such a variety of different styles and eras of skyscrapers living side by side to each other. Every building seems to be built by a different architect from a different walk of life in a different age. Doing a riverboat tour is the best way to see the city and is worth every penny. That way someone clever and charismatic can describe the history and significance of every building on the river front instead of me writing about the “tall, sleek one with the big hole near the top” or the “one that looks like the Daily Bugle where Peter Parker’s boss demands pictures of Spiderman”.

Speaking of Spiderman, the original movies filmed in Chicago several times, featuring shots of the “L” train. No research required for that one, just a core-memory factoid that probably took the space in my brain that was needed to know how to spell orderves. Chicago has a great balance of old and new, rustic and pristine. The “L” train serves as useful public transportation for the city, but the faded iron beams holding it and the screech of the wheels on the tracks also make it feel like a relic. Then there are new things like the riverwalk that add to a modernizing city.

And there is the Bean. Which maybe counts as architecture?

Public transport makes other neighborhoods like Lincoln park, Old Town, and Wrigleyville feel like extensions of the city itself, rather than severed subdivisions. Row housing, townhomes, and smaller apartment buildings have a different charm and offer a different pace than downtown. All in all, a fun place to take long walks. Or runs.

Years ago I was tricked by my sister into running a half marathon in Chicago. Thirteen miles along Lake Shore Drive in South Chicago. We left the hotel before sunrise. The day was beautiful. A cloudless sky and a mild breeze. Hundreds gathered at the starting line ready to put their training to the test. The morning sun sparkled off Lake Michigan and gleamed from the impressive skyline. The starting gun fired, and we were off like cattle being herded from a fenced enclosure. You could not ask for better weather on that early Autumn day. I was completely miserable. This was years ago, and I haven’t run a single day since then. Walking is much better, so just do that.

2. The Drinking

Having drinking as one of the main pillars of a city seems problematic. But this isn’t like Detroit or Gary, Indiana where you drink to try and forget the city you live in. Chicago winters are brutal. There aren’t many outdoor activities available near the city. There’s no skiing. No hiking. Who would want to go boating in January? So why not gather in a warm pub and reminisce with your friends about watching the Bulls in the 90s? Going from the outside air with the icy sting on your face to a toasty, cheery environment with friends who also have flushed cheeks is a cathartic experience. It brings people together. You can see and feel the Irish influence with all the pubs and the radioactive hue of the river on St. Paddy’s day.

I have been myself for St. Paddy’s day. I have consumed the green beer and gazed upon the green river. I have adorned a silly green outfit, even through restaurant reservations for establishments we mistook to be casual. I have drunken Guinness across the city from the Celtic Crossing to the Guinness Storehouse itself. There seems to be an Irish pub on every corner, each one more inviting than the last. I wish I could tell you more specific numbers about Irish immigration to Chicago or pubs per capita, but I already said I would do no research. Just speculation.

One great memory from my most recent time in Chicago was Thanksgiving. My girlfriend and I for some reason decided to visit in the Winter from mid November to mid December. Just my sister, my girlfriend and I celebrated together because we had no other family in town. Limited both in resources and in skill, we crafted instant mashed potatoes and carved a pre-cooked rotisserie chicken. We MacGyver’d some espresso martinis from local liquor store ingredients and had a ball. As the day wore on, we eventually found ourselves at the local Irish pub, where the other patrons had had similar ideas that day. We played darts and sang songs and perhaps one of us snuck out some Smithwick’s under their coat. We had a wonderful time, just the three of us. Now, not to say this can only happen in Chicago. You could swap out “Chicago” with many other cities and it would still be believable (except maybe Mogadishu). But Chicago has a way of greasing the wheels and cultivating a homely aura that is all too inviting.

The city knows what it is and more importantly, what it isn’t. It is the last stop before the Great Plains and the American West. It is a gathering point of weary travelers and hopeful dreamers. The city does not lean on some external allure or bait with tourist traps. This junction of America with brutal winters needs a warm hearth. And these warm hearths need a hardy drink to bring friends and family closer together. Also to forget the cold, of course.

3. The Comedy

A good segue into this would be something my sister took me to called Drunken Shakespeare. In a little room downtown, decorated as a library, a group of five actors perform a Shakespeare play inches away from your feet. They run up and down the stage, they dramatically deliver olde English monologues, and one of them gets drunk. This one actor is randomly selected at the beginning to take 4-5 shots, along with more throughout the play. They still deliver their lines, but many things about the play can be changed. For example, the drunk actor told the narrator he must do an impression for every narration. As the actor gets more belligerent, the show gets funnier, or at least more unhinged.

Alcohol and comedy have been associated since I assume the invention of alcohol. I’m certain after a long day of building pyramids, the workers loved to have a few and laugh at their friend dancing on a table with his pants off. While the two are acquaintances, they are not codependent. One does not rely on the other. I think other aspects of Chicago can make people funny. The meeting point of the Rust Belt, Great Plains, and Midwest bring a variety of faces and backgrounds. I also think long, hard winters make very funny people or very serious people. You can end up like Jim Carrey (Canadian) or Vladimir Putin (Russian). And a breeding ground for comedy draws other funny people.

If you haven’t heard of Second City, check out the Wikipedia page. It is a comedy club that is a jumping off point for so many comics into SNL, movies, TV, and other limelight careers. It’s basically what Duke and KU are for the NBA. The alumni list includes Tina Fey, John Belushi, Bill Murray, Amy Poehler, Chris Farley, Steve Carrell, Stephen Colbert, Racheal Dratch, Keegan-Michael Key, and so many more. More than just Second City, Robin Williams is from Chicago. John C. Reilly is from Chicago. The list goes on forever and I think it’s more than just Chicago being a big city. How many Comedians do you know from Miami? Los Angeles has Hollywood and New York has Broadway to attract performers. In Chicago, you have to be funny to stand out in a city with many funny people already.

We got to see a show at Second City in November of 2023. The show was a balanced blend of improv and sketches and some music and some audience interaction. It was very funny, and not just funny for what passes for comedy these days. I won’t get into how there hasn’t been a true great comedy movie since The Other Guys. But the show was genuinely funny and I’d recommend it to anyone (18 or older).

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There you have it I suppose. Sure there are great museums and food and many other redeeming qualities but these three make the city unique to me. I can’t speak to activities outside the city limits. As long as you like to drink and laugh and walk around aimlessly, Chicago is for you.