Chicago: The heart of the country, a city rebuilt after a devastating fire most likely started by cattle, is the home of deep-dish pizza and the place I call home. I lived in five different neighborhoods for five years, and during that time, I fell in love with it. The rainbow-colored El Train is the fabric of the city, where the skyline grows and reshapes every day, and the streets are brought to life by the people who inhabit this wonderful metropolis.
This city is filled with dreamers, artists, entrepreneurs, comedians, writers—some of the best, let’s be honest. Throughout history, writers like Richard Wright and Stuart Dybek have captured the courage, struggle, and beauty of Chicago in prose and poetry, providing the world with books that will always be treasured. Some of them are particularly emblematic of the Chicago spirit, fraught with issues of race, sexuality, independence and growing up. If you're from Chicago, you probably grew up reading some of these articles, and if not, I highly recommend you put them on your TBR list! Even if you're not a Chicagoan—maybe you're a New Yorker or a Southern girl—there are still plenty of reasons to read these sensational books that take place in the Windy City.
1. “Native Son ” by Richard Wright
When I moved to the city, one of the first books I received was Native Son , which was set in 1930s Chicago and revealed the city's brutal racial divide. The story follows Biggar Thomas, a young man whose fate involves a jail cell, false accusations, and a moment of panic that will define his life. This is a deeply moving novel, and even if you're not from the heart of the Midwest, I would still recommend it to anyone who breathes.
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2. Chicago Shores: The Stuart Dyback Story
What James Joyce was to Ireland, Stuart Dyback was to Chicago. Dybek has some absolutely amazing collections that represent the city of Chicago in so many ways. In "Chicago Shores," you can read his love letter to the city.
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3. Audrey Niffenegger, " The Time Traveler's Wife "
Niffenegger's absolutely stunning debut doesn't take place in downtown Chicago, but it does explore the suburbs and some of the more well-known areas familiar to Chicago locals. Art student Claire and time-traveling librarian Henry meet in a Chicago library—a first meeting for one and a reunion for the other. It's a magical (and heartbreaking) story set near a magical city, and it doesn't get much better than this.
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4. "Damn Hairstyle" by Joe Meno
Joe Meno has written several books that capture the different vibes of Chicago, including "Office Girl" and "The Great Maybe." But my favorite will always be the punk scene’s coming-of-age masterpiece, Hair of the Damn . The protagonist, a burnout named Brian, and his punk rock best friend Gretchen navigate their high school lives and chaotic adolescence together. This novel is set in the era of mixtapes and underground concerts, arcade games and grunge—a place and setting that will captivate you from the first page.
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5. Maud Martha , Gwendolyn Brooks
Brooks gives us a raw look into the lives of young black women in 1950s Chicago that remains relevant today. In short, her writing is timeless. This is a quick read told in a short essay style, but it provides a deep and rich look at social and racial inequality in 1950s Chicago. This is a classic that will stay in your mind long after you've finished reading it.
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6. Bedrock Faith by Eric Charles May
The story of "Bedrock Faith" takes place in a black middle-class community on the South Side of Chicago. The protagonist is Gerald "Stewpot" Reeves, who returns to this community after serving 14 years in prison. The Stewpot returns with a more religious persona and provides endless gossip to his neighbors. The novel has multiple themes, but at its core is a story about the town of Parkland, a place that feels so real and reflects an important part of Chicago that most people don't get the chance to see.
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7. The House on Mango Street , Sandra Cisneros
Chicago is a melting pot of cultures, and The House on Mango Street reflects this in its depiction of the impoverished neighborhood in which protagonist Esperanza Cordero lives. Through a series of vignettes, this is a story about one woman's identity, her independence, her dreams, but it is also the story of all the fascinating people around her. The House on Mango Street is a house close to the hearts of Chicagoans because it perfectly embodies the spirit and promise of the city.
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8. The Devil in the White City by Eric Larson
This nonfiction piece takes you back to the early 1900s, when Chicago hosted the World's Fair. The World's Fair brought prestige, glamor, money... unfortunately, it also brought one of the world's most horrific serial killers, HH Holmes. The book juxtaposes the story of the World's Fair with the story of Holmes' murder and eventual arrest. It's also an interesting look at turn-of-the-century Chicago.
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9. Will Grayson, Will Grayson by John Green and David Levison
Both Green and Levison brought Will Grayson on board for this collaboration. One of them lives in Evanston on the North Shore and the other lives in Naperville in the western suburbs. When they meet on an unlikely street in Chicago, their lives are changed forever. This is a funny read about high school, friendship, and first love, and a book that celebrates the suburbs of Chicago.
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10. Building Stories by Chris Ware
This is a very interesting graphic novel. It takes place in an apartment building in Chicago and follows different characters and their lives inside. A woman in her 30s is looking for her purpose in life, a couple is annoyed by each other's company, and the landlady has been living the same lonely life for decades. The comedy and sadness of everyday life are contained within the beautiful illustrations. If you need a break from a heavy novel, consider picking up this favorite and recommended work of art from Chicago.
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