A Love Letter to Chicago: Sorry I’m a Complete Fuckboy to You

A single woman takes an intermission from the travails of life and an impending massive change, in a city she’s always loved but won’t commit to.

Chicago looking particularly majestic on a blustery day. This photo, and all others in this piece, were taken by me.

I’m a fifth-generation Bronxite with a special place in my heart for the Windy City.

While I did visit Chicago briefly on a family vacation in high school, I don’t remember much about it. I got to see the city’s alternative quarter, The Alley, for a hot second. It was a really cool place, your ideal alt fashion shop, but the area lacked that feeling that this block was meant for a melding of every subculture known to man, and even those unknown and yet to be invented, that we had back home on St. Marks Place and vicinity.

We spent more time with my dad’s friend in Glencoe. He’d come a long way from The Bronx and showed us the Home Alone house, and where The Breakfast Club was filmed. It was nice and I’m glad I got to see it, but seeing a city when you’re a 15-year-old with no money or autonomy is a lot different than being on either side of 29 and financially independent with a life of your own.

I otherwise contextualize Chicago as a city where I made various big steps in my career and life after 30 — this recent trip almost…