8 Books That Will Change the Way You See Chicago

Chicago is, and will always be, a city of layers—concrete and steel, avenues and alleys, history and soul. It’s a place where neighborhoods define much of the identities of its residents, where a single block can hold both beauty and struggle, and where stories unfold in the two-flats, bookstores, and corner bars that line the city’s streets.

The Chicago found in fiction is not always the one found in the posts of social media influencers. At times, it portrays the grittier and more intimate side of the city. Through the eyes of the memorable characters we find in the stories, we have a unique chance to live and experience the version of Chicago that other members of our community do on a daily basis.

In this article, we discuss eight fictional novels set in Chicago, that portray the city in various time periods, as experienced by a diverse group of characters. These stories don’t just romanticize Chicago, but they also challenge our assumptions, and offer glimpses into lives often left out of the official narrative. If you want to know more about the people of Chicago, then these eight novels will help to deepen your understanding of this complex city and its people.

Brian Doyle’s Chicago is a touching, semi-autobiographical novel that captures life in the Windy City In the 1970’s. The story follows a young man who moves to Chicago after college to begin his adult life.

Through his encounters with neighbors, bartenders, taxi drivers, and priests, he learns what is really at the heart of the city. For readers who appreciate character-driven storytelling, Chicago is a great choice.

The Man With the Golden Arm by Nelson Algren is a gritty novel set in Chicago post-World War II. It follows Frankie Machine, a war veteran with a talent for dealing poker and a growing drug addiction, as he struggles to stay clean while living in 1950’s West Town.

Algren paints a vivid portrait of working-class life, capturing the despair, hope, and small acts of resilience that define the lives of the story’s characters. The Man with the Golden Arm is a powerful exploration of addiction, dignity, and survival in a world that offers few chances for escape.

Crossing California is a coming-of-age novel set in Rogers Park and West Rogers Park during the late 1970s. The story follows a group of teenagers as they navigate adolescence, identity, family pressure, and cultural divisions.

The title refers to California Avenue, which acts as a symbolic and literal dividing line between different socioeconomic and ethnic communities on Chicago’s Far North Side. Adam Langer’s story paints a thoughtful and often satirical reflection on the struggle to find meaning and connection in a world shaped by boundaries.

Last Summer on State Street by Toya Wolfe is a powerful debut novel set in the final days of the Robert Taylor Homes public housing complex on Chicago’s South Side. The story follows Felicia “Fe Fe” Stevens, a thoughtful and observant twelve-year-old girl, as she navigates friendship, family, and the impending dissolution of her community.

The novel explores themes of loyalty, loss, identity, and survival, and offers an honest and deeply emotional look at an often overlooked part of Chicago’s past.

Never a City So Real tells a story of Chicago told through a series of character-driven vignettes. Author Alex Kotlowitz takes readers into the lives of everyday Chicagoans from various backgrounds and explores themes such as racial tension and the city’s working-class.

The Great Believers by Rebecca Makkai is a moving novel that shows the impact of the AIDS crisis on a group of friends in Chicago during the 1980s. Makkai’s writing evokes several emotions, and does a wonderful job at capturing both the beauty of chosen family during times of tragedy. The Great Believers is an eye opening novel about how love endures even through loss.

I Am Not Your Perfect Mexican Daughter by Erika L. Sanchez is a poignant coming-of-age novel that explores subjects such as self identity, grief, and the pressure of cultural expectations.

The story follows teenager Julia Reyes as she navigates life and family in Chicago after a tragic accident.Mexican American family in Chicago. Sanchez writes with both brutal honesty and humor, giving voice to a compelling protagonist.

Love at First by Kate Clayborn is a heartfelt romance set in a charming Chicago apartment building. The story centers on Will Sterling, a successful doctor who unexpectedly inherits a unit in the building where he once shared a magical moment in his childhood. He eventually finds himself mixed up with Nora Clarke, one of the building’s residents, who is determined to preserve the building’s community.

Love at First is a slow-burning, but satisfying novel that tells a great story of unexpected love in Chicago.

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