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Chicago’s Underbelly: A Literary Survival Guide

Photo by K Tao

An alternative introduction to experiencing Chicago

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Chicago has had its share of literary coverage, from stories exposing its underbelly to poetry.

Life’s tough in the city. Anywhere really if you’re a working class hero. The stories below shed light on what life is like living in the Windy. Chicago may not be the world’s hog butcher anymore, but it still has quite the underbelly. However, that leftover grit has transformed into an empowering attribute of the city. Without grit, chances of survival are slim.

Stephen Elliot, exposed his darkness (as he so often does), in Where I Slept. The Pacific Garden Mission has been a haven for homeless people for decades, Zac Lowing shares his story of finding hope and how the mission helped him get back on his feet.

Scott shares his avant-garde way of becoming acquainted with a prospective mate. This happened just before the days of Tinder when people spent a little more time online Getting to Know Each Other.

Chicago is beautiful and depending on who you talk to, the weather may not be top of mind unless it’s summer. It may also be reason enough to part with this metropolis. An Arizonian transplant talks about her love/hate relationship in Chicago, I love you but you’re bringing me down. Gabriella shares her sentiment in Please Cover in Winter.

Patrick Chesnut’s fictional piece starts with a kid’s admiration of the city, how it builds on the horizon, and well, you’ll just have to read it in City Work. Chestnut also spins a tale from a Southwest Airline pilot’s point of view in Flyover Drive Through.

After a long day, sometimes you need a drink, a martini in particular with “not so much vermouth”. Allen’s poem captures that moment in Cocktails on Clybourn. Allen also has some staunch guidelines for how to read a piece of poetry in Operating Instructions.

How many times have you had to do a cold meds run in the middle of winter? And how many time have you run into a 12 point buck? Bull Garlington recounts his experience in Deer.

Katya Grokofsky is a feminist artist working and living in NYC. Glitter Bomb is a stream of consciousness writing during her graduate studies at Chicago’s Art Institute about traversing the Atlantic Ocean to come to America.

Lunar Shift is a poem with a little whimsy written by yours truly when I used to look out on Lake Michigan during undergrad. The vastness of the lake was soothing, but the glistening skyline reminded me of how much work I still needed to do. Watching the buildings transform on the water was a momentary escape. There’s also a transit piece I wrote waiting for the red line in Uptown titled Rushtown.

If you even wanted to know what it is like to run a marathon mile by mile, read Ben Gerber’s Race To Finish, he made it the whole way without stopping and may have shed a few tears at the finish line.


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