The Greatest "Chicago, Coming of age" Books of All Time

Click to learn how this list is calculated.

This list represents a comprehensive and trusted collection of the greatest books. Developed through a specialized algorithm, it brings together 300 'best of' book lists to form a definitive guide to the world's most acclaimed books. For those interested in how these books are chosen, additional details can be found on the rankings page.

Filter by: Genres Dates Countries
Follow on:

Genres

Chicago

The "Chicago" category of books refers to literature that is set in or inspired by the city of Chicago. These books may explore the city's rich history, diverse culture, and unique architecture, or delve into the lives of its residents and the challenges they face. From gritty crime novels to heartwarming coming-of-age stories, the Chicago genre encompasses a wide range of themes and styles, all united by their connection to this iconic American city.

Coming of age

The "Coming of age" category of books typically refers to stories that explore the transition from adolescence to adulthood. These books often focus on the challenges and experiences that young people face as they navigate the complexities of growing up, including issues such as identity, relationships, sexuality, and personal growth. Coming of age stories can be set in any time period or cultural context, and may feature protagonists of any gender, race, or background. Overall, the genre offers readers a glimpse into the universal struggles and triumphs of youth, and the process of becoming a fully realized adult.

Add additional genre filters

Countries

Date Range

Filter

Reading Statistics

Click the button below to see how many of these books you've read!

Download

If you're interested in downloading this list as a CSV file for use in a spreadsheet application, you can easily do so by clicking the button below. Please note that to ensure a manageable file size and faster download, the CSV will include details for only the first 500 books.

Download
  1. 1. On the Road by Jack Kerouac

    This novel follows the story of a young man and his friend as they embark on a series of cross-country road trips across America during the late 1940s and early 1950s. The protagonist, driven by a desire for freedom and a quest for identity, encounters a series of eccentric characters and experiences the highs and lows of the Beat Generation. The narrative is a testament to the restlessness of youth and the allure of adventure, underscored by themes of jazz, poetry, and drug use.

  2. 2. The Adventures of Augie March by Saul Bellow

    "The Adventures of Augie March" is a novel set in Chicago during the Great Depression. The story follows the life of Augie March, a poor but spirited boy growing up in a broken home, as he navigates his way through life. The narrative explores his various jobs, relationships, and adventures, as he constantly seeks his identity and place in the world. His journey is marked by a series of encounters with different people and experiences, each shaping him in unique ways.

  3. 3. Sister Carrie by Theodore Dreiser

    The novel follows a young country girl who moves to the big city where she starts realizing her own American Dream by first becoming a mistress to men she perceives as superior and later as a famous actress. It is a portrayal of the realities of the modern city and the complexities of the modern world, illustrating the influence of consumer culture on the individual. Despite her moral decline, the protagonist's rise to fame seems to defy the conventional social norms and moral values, making the novel a notable instance of naturalist literature.

  4. 4. The House on Mango Street by Sandra Cisneros

    The book is a collection of interconnected vignettes that detail the experiences of a Latina girl growing up in the Hispanic quarter of Chicago. It explores her struggles with her identity, her desire for a better life, and her experiences with poverty and gender roles. The protagonist's observations and experiences weave a vivid picture of life in a Latinx community, and her dreams of a better future give the narrative a sense of hope and resilience.

  5. 5. Black Boy by Richard Wright

    "Black Boy" is an autobiographical account of a young African-American boy growing up in the South during the early 20th century. The book explores his experiences with extreme poverty, racism, and his struggle to find his place in a society that marginalizes and devalues him. The protagonist's desire for self-expression and understanding leads him to a love of literature and writing, providing him with a means to challenge and critique the oppressive social structures around him.

  6. 6. Maud Martha by Gwendolyn Brooks

    The novel is a poignant exploration of the inner life of an African American woman navigating the complexities of identity, beauty, and dignity in 1940s Chicago. Through a series of vignettes, the protagonist reflects on the joys and challenges of her everyday experiences, from the nuances of family dynamics and marriage to the sting of racial prejudice and societal expectations. Her journey is one of self-discovery and resilience, as she seeks to affirm her worth and find contentment amidst the often harsh realities of her world.

  7. 7. A Heartbreaking Work of Staggering Genius by Dave Eggers

    A Heartbreaking Work of Staggering Genius is a memoir that follows the life of a young man who, after the cancer-related deaths of his parents, is tasked with raising his 8-year-old brother. The book explores themes of death, family, and the responsibilities that come with sudden adulthood. It is a testament to the strength of the human spirit, showcasing the protagonist's journey through grief, financial struggles, and the challenge of raising a child, all while trying to navigate his own young adulthood.

  8. 8. Studs Lonigan by James T. Farrell

    "Studs Lonigan" is a trilogy that follows the life of an Irish-American man growing up in the South Side of Chicago. His life is marked by aimlessness and self-destruction, as he navigates through adolescence into adulthood against the backdrop of the Great Depression. The protagonist's struggle with his own ambitions, societal pressures, and personal weaknesses provides a stark examination of the human condition and the American Dream.

  9. 9. Jimmy Corrigan, the Smartest Kid on Earth by Chris Ware

    The book is a graphic novel that tells the story of Jimmy Corrigan, an awkward and lonely man in his mid-thirties. Jimmy has lived his entire life under the thumb of his overbearing mother. When he receives a letter from his estranged father, whom he has never met, he embarks on a journey that takes him from his home in Chicago to a small town in Michigan. Along the way, the narrative delves into the lives of his ancestors, revealing a history of loneliness and disappointment that seems to be repeating itself in Jimmy's own life.

  10. 10. Quicksand by Nella Larsen

    "Quicksand" is a semi-autobiographical novel about a mixed-race woman named Helga Crane who, feeling out of place in both African-American and white societies, embarks on a journey of self-discovery. From the Southern United States to Denmark and back, she struggles with racial identity, sexual repression, and societal expectations, eventually marrying a reverend and becoming disillusioned with her life as a preacher's wife in the rural South. The novel explores themes of racial identity, class, and gender in the early 20th century.

  11. 11. The Help by Kathryn Stockett

    Set in the early 1960s in Jackson, Mississippi, the story revolves around three main characters: two black maids and a young white woman. The maids, who have spent their lives taking care of white families and raising their children, agree to share their experiences with the young woman, who is an aspiring writer. The book offers a poignant and humorous look at the complex relationships between these women, while also exploring the racial tensions and social changes of the era.

  12. 12. The Last Samurai by Helen DeWitt

    "The Last Samurai" is a unique, intellectual novel that follows the life of a young boy named Ludo, who is raised by his single mother, Sibylla. Sibylla, a freelance transcriber, educates Ludo in various subjects from Greek to mathematics, using the film "The Seven Samurai" as a moral compass. As Ludo grows older, he embarks on a quest to find his father, using clues from his mother's past. His journey leads him to several men who could potentially be his father, each encounter teaching him more about the world and himself.

  13. 13. The Great Believers by Rebecca Makkai

    "The Great Believers" by Rebecca Makkai is a powerful novel that tells the story of two interconnected groups of people: a group of gay men in 1980s Chicago during the height of the AIDS epidemic, and a woman in 2015 who is searching for her estranged daughter in Paris. The novel explores themes of love, loss, friendship, and the devastating impact of the AIDS crisis. Makkai's writing is both heartbreaking and hopeful, and she skillfully weaves together the two timelines to create a poignant and unforgettable story.

  14. 14. Aquamarine by Carol Anshaw

    "Aquamarine" is a novel that explores the divergent paths that a woman's life could take after a pivotal event. The story centers on a competitive swimmer whose life splits into three distinct trajectories following her participation in the Olympics. Each narrative thread examines the different directions her life could have taken, delving into themes of love, regret, and the choices that define us. The novel weaves these alternate realities together, offering a poignant look at the what-ifs that haunt our lives and the ways in which a single moment can have a ripple effect on our existence.

  15. 15. 18% Gray by Zachary Karabashliev

    In this gripping novel, a man finds himself at a crossroads in life, grappling with the loss of his wife and the disintegration of his marriage. In a spontaneous attempt to escape his pain and find meaning, he embarks on a transformative journey across America with a stolen stash of marijuana and a camera, capturing moments of beauty and introspection. As he travels from the East to the West Coast, his road trip becomes a quest for redemption and self-discovery, revealing the complexities of love, memory, and the pursuit of happiness.

  16. 16. Caramelo by Sandra Cisneros

    This novel is a rich tapestry of family history and Mexican and American cultures, told through the eyes of a young girl, Lala Reyes, during her annual road trips to Mexico City. The narrative weaves through generations, focusing on the complexities of family dynamics, identity, and the search for one's place within two cultures. Central to the story is the symbolic caramelo rebozo, a striped shawl inherited from Lala's grandmother, which serves as a metaphor for the blending of traditions, histories, and the colorful stories that make up Lala's heritage. Through vivid storytelling, the book explores themes of memory, storytelling, and the immigrant experience, offering a poignant look at the bonds that tie families together across borders and generations.

  17. 17. Paper Fish by Tina de Rosa

    "Paper Fish" is a poignant novel set in Chicago's Italian-American neighborhood during the 1940s and 1950s. The story centers around Carmolina BellaCasa, a young girl navigating the complexities of her family's past and the cultural tensions of her immigrant community. As she grows, Carmolina grapples with her mother's mental illness and the haunting memories of her grandmother's struggles in Italy, all while trying to find her own identity. The narrative beautifully captures the essence of memory and the impact of heritage on personal identity, weaving a rich tapestry of community life, familial bonds, and the enduring strength of women.

  18. 18. So Big by Edna Ferber

    "So Big" is a novel that follows the life of Selina Peake De Jong, a woman who moves from Chicago to a rural Dutch community in Illinois after the death of her father. She becomes a school teacher and marries a farmer, living a life of hardship and poverty. Despite the challenges, she instills a love of beauty and art in her son Dirk, who grows up to become a successful architect. The book explores themes of resilience, the American Dream, and the often overlooked value of hard work and artistic integrity.

  19. 19. Years of Grace by Margaret Ayer Barnes

    "Years of Grace" is a novel that follows the life of a woman named Jane Ward Carver from her adolescence in the late 19th century to her adulthood in the early 20th century. The book explores her struggles and triumphs in navigating societal expectations, love, marriage, and motherhood in a rapidly changing world. The story is set against the backdrop of significant historical events, including World War I and the Roaring Twenties, providing a rich and detailed portrait of a woman's life during this transformative era.

  20. 20. My Favorite Thing Is Monsters Vol. 1 by Emil Ferris

    "My Favorite Thing Is Monsters Vol. 1" is a graphic novel that follows the story of Karen Reyes, a ten-year-old girl living in 1960s Chicago. Through her vivid imagination and artistic talent, Karen transforms herself into a monster to navigate the complexities of her life, including her brother's mysterious death and her mother's illness. As she uncovers secrets and delves into the dark underbelly of her neighborhood, Karen's journey becomes a poignant exploration of identity, family, and the power of art.

Reading Statistics

Click the button below to see how many of these books you've read!

Download

If you're interested in downloading this list as a CSV file for use in a spreadsheet application, you can easily do so by clicking the button below. Please note that to ensure a manageable file size and faster download, the CSV will include details for only the first 500 books.

Download