My First Week In Chicago: Apparently Pants Are Optional

I moved to Chicago expecting a lot of things: architecture, traffic, public transportation, maybe a deep-dish pizza-induced medical emergency.

What I did not anticipate was that, within my first few days, I would find the cutest little coffee shop in my neighborhood and immediately discover a man standing outside in his underwear. Not near the coffee shop. Not walking quickly away from an unfortunate laundry-related incident. Just standing there. In his underwear. I had been in Chicago for approximately five minutes, and public trouser compliance was already concerning.

The next morning, I headed out to catch the bus because I am determined to become one of those competent city people who understands public transportation. I found the sign, stood beneath it, and waited. Eventually, I began to suspect something was wrong.

There was no bus because I was not standing at a bus stop. I was standing beneath a snow route sign. In August.

This felt like information I probably should have gathered before confidently positioning myself there like a local.

I eventually found the actual bus stop, and lying beside it were a pair of pants — the day after I had seen a man standing on the sidewalk in his underwear. I cannot prove they were his. But I also cannot prove they weren’t.

Suddenly, Chicago had presented me with a mystery: Day One: man with no pants. Day Two: pants with no man. I’m not saying I solved the case. I’m just saying the evidence is compelling.

Public transportation has also been an adjustment, but the train was actually one of the things I was most excited about before I moved. Before I got here, someone tried to explain the L to me and I could not wrap my mind around it, so naturally, I Googled pictures.

My immediate reaction was, Oh my God. It’s up in the sky.

I understand intellectually that “elevated train” is a perfectly reasonable explanation. There are tracks. There are supports. Physics is involved. None of that mattered. In my head, Chicago had a flying train, and I could not wait to ride it.

The first time I actually did, I looked out the window at the buildings passing beside me and had exactly the same reaction: Oh my God. The train is flying.

Rationally, I understand that it is an elevated train running on tracks. Emotionally?

Flying train.

Naturally, I loved it. This is how Chicago and I seem to be getting to know each other.

I moved here with my entire life stuffed into a car and my cat, Delilah, riding shotgun like a tiny disgruntled navigator who had not been consulted about the relocation. There was nothing glamorous about the arrival — trash bags full of clothes, random household objects shoved into whatever space remained, and a cat looking at me as though she had retained legal counsel.

But somewhere between unloading the car and realizing I actually lived here now, something strange happened. Chicago stopped being a place I was moving to. It became the place I was standing.

That sounds obvious until you’ve spent months saying things like, When I get to Chicago… When I get to Chicago, I’ll do this. When I get to Chicago, I’ll go there. When I get to Chicago, maybe my whole life will finally make sense.

Then you arrive and discover your new life does not announce itself with orchestral music. It starts with groceries, parking, figuring out which train goes where, and, apparently, a man in his underwear standing outside a coffee shop.

A couple of days later, I saw an older gentleman driving what appeared to be a golf cart while wearing something that looked suspiciously like a kimono. Nobody around him seemed particularly concerned. I wasn’t concerned in a negative way. I was concerned in a what exactly are the rules here? way.

Chicago considers rules more of a collaborative suggestion. This is especially challenging for me because, despite everything else about my personality suggesting otherwise, I am a ridiculous rule follower. I stop completely at stop signs. I return shopping carts. If a sign says “Do Not Enter,” I assume it has a compelling reason.

Chicago does not seem similarly burdened. Red lights? Suggestions. Lane markings? Aspirational. Crosswalks? A group negotiation. I keep looking around like, Are we all seeing the same signs? Apparently we are. We have simply reached different conclusions.

And somehow, I love that too.

Then there was the ice cream truck, which requires a little history. Years ago, I once became so convinced I heard an ice cream truck that I practically yeeted myself out of a car in pursuit of it.

It was a gazebo.

To this day, I cannot adequately explain how I confused a stationary wooden structure with a mobile frozen-dessert vendor, but there are certain questions science may never answer.

So naturally, within days of moving to Chicago, I was sitting outside when I heard an actual ice cream truck drive by. This time, thankfully, it was not a gazebo. Maybe that was Chicago’s way of welcoming me: Here. We heard about the incident. Have a real one.

I also discovered something I didn’t expect. I thought moving here might feel dramatic. Chicago had lived in my imagination for a long time before it became my address, and I expected some enormous emotional reaction when I finally arrived.

Instead, it feels surprisingly normal. Good normal.

I walk around my neighborhood. I notice buildings. I listen to the train. I find places I want to return to. I sit in my little coffee shop and write. That’s the part I keep coming back to.

For years, I said I wanted to write. Then I started writing. Then somewhere along the way, I began reluctantly admitting that maybe I was a writer.

And now I’m sitting in a coffee shop in Chicago with my laptop open, writing about the fact that everyone is wearing pants today.

Maybe this is the dream. Not the pants specifically, although it’s reassuring. The life. The ordinary little life I kept imagining from somewhere else.

This weekend, I wandered through the Harold Washington Library and got lost on purpose. Somewhere in the middle of all that, I became an official Chicagoan.

Not because I signed a lease. Not because I figured out the CTA. Not because I survived traffic without openly weeping.

Because I got a Chicago Public Library card.

I could have unpacked every box in my apartment and still felt like I was visiting. But hand me a library card with my name on it?

Citizen.

It turns out my path to belonging has always involved books.

I spent so much of my life thinking the important moments would announce themselves. I wondered what it would feel like to finally live in Chicago.

Turns out it feels like coffee shops, confusing bus stops, mysterious pants, questionable traffic laws, a flying train, and a library card in my wallet.

Honestly, I think I’m doing this exactly right.

In other words, I think we’re going to get along just fine.