The Greatest "Chicago, Contemporary" Books of All Time

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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.

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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.

Contemporary

Contemporary books are a genre that focuses on stories set in the present day, often exploring current social, cultural, and political issues. These books are typically written in a modern style and often feature relatable characters dealing with real-life situations. Contemporary books can cover a wide range of topics, from romance and family drama to coming-of-age stories and thrillers. The genre is constantly evolving to reflect the changing world we live in, making it a popular choice for readers who want to stay up-to-date with the latest trends and issues.

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  1. 1. Herzog by Saul Bellow

    The novel centers around Moses Herzog, a middle-aged, intelligent yet distressed man who is going through a mid-life crisis. After his second marriage fails, he falls into a state of emotional turmoil and begins writing letters to friends, family, and even famous figures, expressing his philosophical thoughts and personal feelings. His journey of self-discovery and understanding forms the crux of the story. It's a profound exploration of a man's struggle with the complexities of life and his quest for meaning.

  2. 2. Humboldt's Gift by Saul Bellow

    This novel explores the friendship between a successful writer and his mentor, a once-celebrated poet now living in poverty and mental instability. As the protagonist navigates his own existential crisis amidst a life of material success, he reflects on the ideals of his mentor and the nature of art and personal ambition. The narrative grapples with themes of materialism, the purpose of art, and the spiritual emptiness of modern life.

  3. 3. 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.

  4. 4. 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.

  5. 5. 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.

  6. 6. Nowhere Man by Aleksandar Hemon

    "Nowhere Man" is a unique narrative that explores the life of a Bosnian immigrant who is trapped in Chicago during the outbreak of the Bosnian war. The novel uses a non-linear narrative structure and multiple perspectives to tell the story of the protagonist's life, from his childhood in Sarajevo, to his struggles and experiences in America. The book is a poignant examination of identity, displacement, and the immigrant experience.

  7. 7. Talk Before Sleep by Elizabeth Berg

    "Talk Before Sleep" is a heartfelt novel that explores the profound bond between two women as they navigate the trials and tribulations of life. When one of them is diagnosed with breast cancer, their friendship is tested in unimaginable ways. As they grapple with the harsh realities of illness, they find solace in each other, sharing their deepest fears, hopes, and dreams in the quiet hours of the night. The narrative is a poignant exploration of friendship, love, and the human capacity for resilience in the face of adversity.

  8. 8. Then We Came To The End by Joshua Ferris

    "Then We Came To The End" is a satirical novel that follows the lives of a group of advertising agency employees during a time of layoffs and uncertainty in the early 2000s. The story is told from the perspective of an unnamed narrator and explores the dynamics of office politics, relationships, and the struggle to maintain a sense of purpose and identity in the face of corporate downsizing. The novel is a witty and insightful commentary on modern work culture and the human condition.

  9. 9. Building Stories by Chris Ware

    "Building Stories" is a unique graphic novel that explores the lives of the residents of a three-story Chicago apartment building, including a lonely single woman, a couple embroiled in a failing marriage, and the building's elderly landlady. The narrative is presented in a box containing 14 different printed works including books, newspapers, and pamphlets, each offering a different perspective on the characters' lives, struggles, and dreams. The innovative format allows readers to choose their own path through the interwoven stories, resulting in a deeply immersive and interactive reading experience.

  10. 10. The Lazarus Project by Aleksandar Hemon

    The novel follows two intertwined narratives. In the first, set in 1908, a Jewish immigrant is wrongfully accused of anarchism and murdered by the Chicago Chief of Police. In the second, set in modern times, a writer from Eastern Europe is investigating the century-old murder, leading him on a journey across Eastern Europe and eventually back to the United States. The narratives explore themes of love, immigration, and the pursuit of the American dream.

  11. 11. Rails Under My Back by Jeffery Renard Allen

    The novel is a sweeping narrative that explores the complexities of African American life and the enduring impact of family legacy through the story of two brothers and their extended families. Moving back and forth in time and place, the book weaves together the brothers' lives, their relationships, and their struggles with identity, migration, and belonging. The narrative delves into the broader African American experience, touching on themes of love, faith, suffering, and redemption, while painting a vivid portrait of twentieth-century America and the historical forces shaping the characters' lives.

  12. 12. The Hating Game by Sally Thorne

    In this delightful romantic comedy, Lucy and Joshua are co-workers who despise each other. Constantly engaged in a battle of wits and pranks, their intense rivalry begins to blur the lines between love and hate. As they compete for a promotion, their relationship takes unexpected turns, revealing hidden feelings and a deeper connection. With a mix of humor, chemistry, and undeniable attraction, "The Hating Game" explores the thin line between love and hate in a workplace setting.

  13. 13. Larry's Party by Carol Shields

    Larry's Party is a thought-provoking novel that follows the life of Larry Weller, a man who finds his true passion in creating mazes. As Larry navigates through different stages of his life, the book explores themes of identity, relationships, and the search for meaning. Through Larry's experiences, readers are compelled to reflect on their own journeys and the choices they make along the way.

  14. 14. The Unnamed by Joshua Ferris

    This novel explores the life of a successful lawyer who is afflicted with a mysterious condition that compels him to walk without any control over when or where. His uncontrollable walks disrupt his professional life and strain his family relationships, leading to a profound examination of identity, mental illness, and the impermanence of life. As he grapples with his condition, the narrative delves into themes of love, the essence of self, and the search for meaning in a seemingly indifferent universe. Through his journey, the protagonist confronts the fundamental question of what it means to truly live when one's basic autonomy is stripped away.

  15. 15. The Middlesteins by Jami Attenberg

    This novel explores the complexities of family dynamics, focusing on the Middlestein family, who are grappling with various personal and collective crises, primarily revolving around Edie, the matriarch's, struggle with obesity and its impact on her health and relationships. As Edie's condition worsens, her family's reactions reveal their individual struggles, insecurities, and the ways in which they cope with stress and change. Through a narrative that is both compassionate and unflinching, the book delves into themes of love, loyalty, and the challenges of caring for someone who seems beyond help, all while painting a vivid portrait of contemporary American life and the ways in which personal and familial histories intertwine.

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