The Greatest "Chicago, Fiction" 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 305 '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.

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  1. 26. The Asphalt Jungle by W. R. Burnett

    This novel delves into the gritty underworld of urban crime, focusing on a meticulously planned jewelry heist that promises to be the ultimate payday for its diverse crew of small-time crooks and down-on-their-luck characters. However, as the operation unfolds, the group's carefully laid plans begin to unravel due to a mix of greed, betrayal, and the relentless pressure from law enforcement. Set against the backdrop of a bleak, post-war American city, the narrative explores themes of desperation, the elusive American dream, and the thin line between order and chaos in the pursuit of survival and redemption.

    The 2306th Greatest Book of All Time
  2. 27. Dangling Man by Saul Bellow

    Set in Chicago during World War II, the novel follows the life of a young man waiting to be drafted into the army. As he waits, he grapples with his feelings of isolation, frustration, and anxiety, which are exacerbated by his joblessness and the uncertainty of his future. His diary entries reveal his philosophical reflections on life, his struggles in his relationships, and his increasing mental instability as he feels more and more trapped by his circumstances.

    The 2443rd Greatest Book of All Time
  3. 28. 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.

    The 2692nd Greatest Book of All Time
  4. 29. Left Behind by Tim LaHaye, Jerry B. Jenkins

    "Left Behind" is a gripping story set in the aftermath of the Rapture, when millions of people around the world suddenly disappear, leaving behind everything but their clothes and personal belongings. The novel follows a group of survivors, including a commercial airline pilot, a journalist, and a college student, as they navigate the chaos and confusion of a world in crisis. As they search for answers and try to understand what has happened, they are drawn to the words of the Bible, which seem to predict the events unfolding around them. Together, they form the Tribulation Force, a group dedicated to fighting the forces of evil and spreading the word of God in a world on the brink of the Apocalypse.

    The 2736th Greatest Book of All Time
  5. 30. Jennie Gerhardt by Theodore Dreiser

    This novel tells the poignant story of Jennie Gerhardt, a young woman of humble origins who, through a series of unfortunate circumstances and societal pressures, becomes involved with two different men of higher social standing throughout her life. Set against the backdrop of late 19th-century America, the narrative explores themes of love, class disparity, and the struggle for personal dignity. Jennie's character embodies resilience and moral complexity as she navigates the challenges posed by her relationships and the harsh judgments of society, ultimately highlighting the human capacity for endurance and the quest for happiness amidst societal constraints.

    The 2845th Greatest Book of All Time
  6. 31. A Street In Bronzeville by Gwendolyn Brooks

    This book is a poignant collection of poetry that explores the lives and struggles of African Americans in the mid-20th century urban landscape. Through vivid imagery and emotional depth, the poems delve into themes of racial identity, social injustice, and the search for personal meaning within the confines of a segregated society. The poet's keen observations and lyrical mastery bring to life the vibrant community of Bronzeville, a neighborhood in Chicago, capturing both its beauty and its hardships, and offering a powerful commentary on the broader African American experience during this era.

    The 2898th Greatest Book of All Time
  7. 32. Eight Men: Short Stories by Richard Wright

    "Eight Men: Short Stories" is a collection of tales that explore the lives of African-American men in a racially divided America. Each story delves into the experiences of these men as they navigate through the complexities of their existence, facing racial prejudice, social injustice, and personal dilemmas. The stories are a poignant portrayal of their struggles and resilience, offering a profound commentary on race relations and the human condition.

    The 2942nd Greatest Book of All Time
  8. 33. More Die Of Heartbreak by Saul Bellow

    This novel delves into the complex relationship between an uncle, a renowned botanist, and his nephew, a reflective and somewhat aimless academic. Through their intertwined lives, the narrative explores themes of love, intellectualism, and the pursuit of happiness in a modern world that often seems at odds with the desires of the heart. The uncle's disastrous romantic entanglements and the nephew's philosophical musings on civilization and its discontents serve as a backdrop to a story that examines the human condition, the quest for meaningful connections, and the irony that, despite advances in society, individuals still suffer from emotional turmoil and dissatisfaction.

    The 3169th Greatest Book of All Time
  9. 34. The 42nd Parallel by John Dos Passos

    "The 42nd Parallel" is a novel that explores the lives of several characters in the early 20th century United States. The narrative intertwines the stories of five protagonists as they navigate through various historical events and social changes such as labor strikes, World War I, and the Mexican Revolution. The book is notable for its experimental style, which includes the use of "Newsreel" and "Camera Eye" sections that incorporate newspaper clippings, song lyrics, and stream-of-consciousness writing to reflect the chaotic and rapidly changing times.

    The 3244th Greatest Book of All Time
  10. 35. Street Games by Rosellen Brown

    "Street Games" is a collection of short stories that delve into the complexities of human relationships and the nuanced experiences of life in urban settings. The narratives explore themes of love, loss, and the struggle for personal identity, often against the backdrop of societal expectations and the gritty realities of city life. Each story serves as a vignette, offering a window into the lives of diverse characters as they navigate the challenges and triumphs of their everyday existence, revealing the profound impact of seemingly ordinary moments and the power of connection in the face of adversity.

    The 3462nd Greatest Book of All Time
  11. 36. 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.

    The 3617th Greatest Book of All Time
  12. 37. The Unpleasant Profession Of Jonathan Hoag by Robert A. Heinlein

    In this speculative fiction novel, a man with no memory of his daytime activities hires a husband-and-wife detective team to follow him and uncover the truth about his mysterious occupation. As the detectives delve deeper into the case, they find themselves entangled in a surreal, nightmarish world that challenges their understanding of reality. The investigation leads them to confront a secret society and a reality-altering substance, culminating in a confrontation with the very nature of existence and the role their client plays in maintaining the balance between good and evil.

    The 3791st Greatest Book of All Time
  13. 38. Brewster's Millions by Richard Greaves

    In this classic comedic novel, the protagonist is tasked with an unusual and seemingly enviable challenge: to spend a vast fortune of one million dollars within a year in order to inherit an even greater sum of twenty million dollars. The catch is that he must do so without acquiring any tangible assets or revealing the conditions of the will to anyone else. This seemingly delightful opportunity quickly becomes a source of frustration and comedy as the protagonist navigates the pitfalls of extravagance, the complexities of human nature, and the true value of money, all while trying to maintain his sanity and integrity amidst the lavish and often absurd spending spree.

    The 4151st Greatest Book of All Time
  14. 39. Nineteen Nineteen by John Dos Passos

    "Nineteen Nineteen" is the second novel in a trilogy that explores the social and political changes in the United States during the early 20th century. It uses a unique narrative style that blends traditional storytelling with newspaper clippings, song lyrics, and biographies of historical figures. The book focuses on the year 1919, a time of significant upheaval in America and abroad, and follows a diverse group of characters as they navigate these tumultuous times.

    The 4151st Greatest Book of All Time
  15. 40. Laura by Vera Caspary

    The novel revolves around the investigation into the murder of a beautiful and successful advertising executive, whose charm and elegance have captivated many men. As the detective delves into her life, he becomes increasingly obsessed with the victim, piecing together her complex relationships and the events leading up to her death. Through a series of twists and character revelations, the story explores themes of obsession, identity, and the facades people construct in their lives. The detective's journey through the victim's world blurs the lines between professional duty and personal fixation, leading to a surprising resolution that challenges his initial perceptions.

    The 4537th Greatest Book of All Time
  16. 41. Little Caesar by W. R. Burnett

    The book is a gritty tale of the rise and fall of a small-time hoodlum who becomes a powerful gangster in the criminal underworld. Set in the Prohibition era, it follows the ambitious and ruthless protagonist as he climbs the ranks of organized crime, driven by a desire for power and recognition. His journey is marked by violence, betrayal, and the harsh realities of gang life. As he achieves his goals, he becomes increasingly isolated and paranoid, ultimately leading to his downfall. The novel is a stark exploration of the American Dream gone awry, illustrating the cost of unchecked ambition and the inevitable consequences of a life of crime.

    The 4588th Greatest Book of All Time
  17. 42. 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.

    The 5147th Greatest Book of All Time
  18. 43. Dead Time by Eleanor Taylor Bland

    "Dead Time" is a gripping crime novel that follows the determined and resourceful African-American police detective, Marti MacAlister, as she investigates a series of mysterious deaths in a small Midwestern town. As the body count rises, Marti must navigate through a web of secrets and lies, uncovering shocking truths about the victims and their connections, while also facing personal demons from her own past. With a strong female protagonist, intricate plot twists, and a vividly described setting, this book keeps readers on the edge of their seats until the final page.

    The 5329th Greatest Book of All Time
  19. 44. 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.

    The 5329th Greatest Book of All Time
  20. 45. Against the Day by Thomas Pynchon

    The novel is a sprawling epic that spans the period from the 1893 World's Fair to the years following World War I. It follows the stories of several characters including the anarchist Traverse family, a group of balloonists, a detective, and a mathematician. The book explores themes of anarchism, capitalism, and technology, and incorporates elements of science fiction, adventure, and historical fiction. It is noted for its complex structure and dense, multifaceted narrative.

    The 5683rd Greatest Book of All Time
  21. 46. Sexual Perversity in Chicago by David Mamet

    "Sexual Perversity in Chicago" is a play that explores the relationships and sexual dynamics of two young couples in 1970s Chicago. The narrative dissects the complex nature of sexual relationships, highlighting the characters' struggles with intimacy, communication, and emotional honesty. The play uses humor and sharp dialogue to delve into themes of gender roles, sexual politics, and the difficulty of establishing genuine connections in a culture saturated with false and damaging representations of love and sex.

    The 5738th Greatest Book of All Time
  22. 47. A Million Little Pieces by James Frey

    The book is a controversial memoir that details the author's intense struggle with addiction, chronicling his experiences from the depths of substance abuse to the painful path of recovery. It vividly portrays his time in a rehabilitation facility, the colorful characters he meets there, and the personal demons he battles along the way. The narrative delves into themes of redemption, the harsh realities of addiction, and the complex journey towards self-forgiveness and healing, despite later being revealed to contain fabrications and embellishments of the author's experiences.

    The 5851st Greatest Book of All Time
  23. 48. 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.

    The 6261st Greatest Book of All Time
  24. 49. 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.

    The 6401st Greatest Book of All Time
  25. 50. Hardball by Sara Paretsky

    In this gripping detective novel, a tenacious female private investigator delves into the murky depths of Chicago's political landscape to solve the murder of a reporter. As she navigates the treacherous waters of corruption, organized crime, and the city's power elite, she uncovers a complex web of deceit that threatens to engulf her. With her sharp wit and unwavering determination, she confronts the dangerous forces at play, risking her own life to bring justice to the forefront in a world where playing hardball can have deadly consequences.

    The 6403rd Greatest Book of All Time

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