Getting to Know Chicago

Christopher Bigelow
4 min readMay 1, 2022
Photo by Muzammil Soorma on Unsplash

2022 will be the second time I have repotted my life from one city to another. Eleven years ago, I ran away from my rural home for the bustle and anonymity-as-safety of New York City. In a speech at my high school graduation a few months before the move, I remarked about how different my life would be when there were more people in my apartment building than in my entire hometown, but intellectually anticipating the rural-urban divide is nothing to experiencing it.

New York City was overstimulating in all of the best ways. Insecure in my vision (legal blindness uncorrected for ten years will do that to you) and never able to make that extension-of-your-body connection with motor vehicles, the ability to walk and take mass transit was a dream. That there were twenty-seven different subway lines was daunting, but a worthy challenge.

The subways became the cornerstone of my transition to New Yorker.

Knowing basically no one and starting with a deficit of social skills from years of relative isolation, I set out alone to learn all I could about my new home. To do that, I rode the subway.

I started with the closest line to my dorm, the 1 train. I got on at 137th Street, headed northbound, rode to the end of the line, crossed the platform, and headed to the other end. I did the same thing over many weeks, reaching the terminal points of every one of those lines.

It was weeks before I was brave enough to explore the city on land, but by then I was no longer alone. I began to set roots in Harlem, Brooklyn, the Lower East Side, and southeastern Queens. It wasn’t long before I was a human GPS, more at ease with the MTA than even native New Yorkers. There’s no zealot like a convert, I guess.

Now that I’m preparing to leave New York — the only home I recognize — I am thinking a lot about how I will honor and get to know Chicago, where I hope I’ll make my forever home. I’ll be making the move in just under sixty days, adding a level of urgency.

I have, admittedly, done some exploring already–walking ten miles in a day more than a few times this summer, but I’m looking forward to digging in even more. Here are a few of the ideas I have in getting to know Chicago as part of my new resident initiation:

  • Visit every branch of the Chicago Public Library, review them on Instagram, and post some piece of writing I produced there on this page — I don’t know where this idea came from but I’ve been obsessed with it from the moment it was conceived. I also doubt that any branch will even hold a candle to my beloved Harold Washington, but that’s unfair competition.
  • Vote against Lori Lightfoot in the 2022 primary — Absentee ballot incoming!
  • Spend a day in each of Chicago’s major museums, become a member of one — If I had to make a bet, I’d bet on the Adler, but I surprise myself every day.
  • Spend a day in as many of Chicago’s minor museums as possible, become a member of one of those too — Next on the list: the Medieval Torture Museum.
  • Find out how many shots of Malört it takes to make it not taste like a New York City street on trash day in July smells — It’s definitely not two.
  • See at least one show at as many Chicago theaters as I can, big and small — Due to COVID, I haven’t been to as many as I’d like, and I’m so excited.
  • Collect street fests and farmer’s markets
  • Attend the Chicago Pen Show, Printers Row Lit Fest, and the American Writers Festival
  • Pay attention to local politics in a way I never did in New York — I recently started listening to the Ben Joravsky Show (Shout out to the newly-liberated Chicago Reader!) and I have to say, Chicago Alderpeople are just more interesting.
  • Go to (more) Cubs Games
  • Go to at least one Bulls, Bears, Sky, and Bandits game
  • Witness Chicagohenge
  • Go to a music festival — by which I mean, get dragged to Riot Fest with my partner, hate it the entire time, whine like a little bitch, and then pretend that I had the time of my life afterward.
  • Get a car and some throwaway object worthy to be my dibs — digging out cars in these streets is NO JOKE.
  • Get “hometown” tattoos — This is the sentimental pushover in me, I like tattoos that mark stages in my life. Something that commemorates NYC and one that commemorates Chicago feels like a beautiful living memorial.

I’m open to any suggestions. Drop yours in the comments!

  • Disclaimer — any anti-Chicago bullshit will be deleted.

Camp NaNoWriMo Day 29

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Christopher Bigelow

Queer Storyteller and Educator. I write about fiction and nonfiction in all forms. 🏳️‍⚧️🏳️‍🌈 christopherbigelow.substack.com