Here are some wonderful books where the city of Chicago feels alive on the page. Each story uses the city’s streets, neighborhoods, and history in unique ways.
You’ll find everything from historical dramas and mysteries to futuristic adventures and personal journeys, all rooted in this distinct American city.
This is a tough, essential read. Richard Wright introduces Bigger Thomas, a young Black man hemmed in by poverty and racism in 1930s Chicago. A terrible accident occurs, not entirely his fault, but it sets off a chain reaction.
His attempts to escape the consequences only pull him deeper into trouble. The story examines how fear and lack of opportunity can shape a person’s choices.
Saul Bellow’s book follows Augie March, who grows up during the Great Depression in Chicago. Augie is restless; he moves from one situation to another, always looking for something more. He gets involved with all sorts of people and tries many different jobs.
You really get a feel for the energy and chaos of Chicago through his experiences.
Alaa Al Aswany focuses on a community of Egyptian immigrants connected to a Chicago university. Their lives intersect, and the novel explores their feelings about identity, politics back home, and fitting into American culture.
There’s a professor troubled by past decisions and a student torn between his own goals and his community’s expectations. It gives a real sense of their struggles and triumphs in a new place.
Veronica Roth imagines a future Chicago walled off from the world. Society is split into five groups, or factions, based on personality traits: honesty, selflessness, bravery, peacefulness, and intelligence.
Beatrice “Tris” Prior learns she doesn’t fit perfectly into any single faction. This makes her “Divergent,” which is incredibly dangerous. She has to hide her true nature while navigating the brutal initiation into her chosen faction, Dauntless (the brave).
She starts to uncover secrets about the system that could tear her world apart.
Sandra Cisneros tells this story through short, memorable pieces. Esperanza Cordero is a young Latina girl growing up in a Chicago neighborhood. She observes her family, her neighbors, and the world from her house on Mango Street.
She dreams of a different life, a house all her own, away from the limitations she feels. Esperanza’s voice is clear and hopeful, even when she describes difficult things.
Upton Sinclair wrote this novel to expose awful conditions. Jurgis Rudkus, an immigrant from Lithuania, arrives in Chicago with his family, full of hope. They find work in the meatpacking plants of the Packingtown district.
Instead of the American dream, they face brutal exploitation, dangerous work, terrible sanitation, and corruption. Jurgis’s story is heartbreaking as he fights to survive. Sinclair famously detailed the unsanitary practices in the meat industry here.
Nelson Algren takes you into the gritty world of post-WWII Chicago. Frankie Machine is a talented card dealer (the “golden arm”) but struggles with morphine addiction. He’s caught between his life on Division Street, his wife Zosh, his friend Sparrow, and his love for Molly.
The book gives a raw look at people living on the margins, full of desperation but also moments of connection.
This is the final book in the Divergent trilogy. Tris and Tobias learn that their whole society, the faction system in Chicago, was an experiment. They decide to venture beyond the city’s fence with a small group.
What they find outside forces them to question everything they believed about their world and themselves. The narrative switches between Tris’s and Tobias’s points of view, so you see events through both their eyes as they face new dangers.
Mitch Glazer adapted the screenplay for the famous movie into this novel. Jake and Elwood Blues are on a “mission from God.” They need to raise $5,000 to save the orphanage where they grew up. Their plan involves getting their old blues band back together for a big show.
Of course, nothing goes smoothly. They cause chaos across Chicago and Illinois, pursued by police, neo-Nazis, and a vengeful country band. It’s a hilarious, music-filled ride.
Rebecca Makkai weaves together two timelines. In 1980s Chicago, Yale Tishman and his circle of friends navigate the art world and their relationships just as the AIDS epidemic begins to devastate their community.
Decades later, in 2015, Fiona, the sister of one of Yale’s friends, travels to Paris. She is searching for her estranged daughter and reflects on the losses of the past. The book explores friendship, art, loss, and the long shadow of grief.
This book introduces V.I. Warshawski, a tough female private investigator in Chicago. She gets hired to find a missing university student. What seems like a simple case quickly entangles her in a much larger conspiracy involving insurance fraud, murder, and powerful figures.
V.I. uses her wits and street smarts to navigate the city’s dangers.
Theodore Dreiser’s novel follows Caroline “Carrie” Meeber. She moves from a small town to the bustling city of Chicago around the turn of the 20th century, hoping for a better life. Initially naive, she is soon drawn to the city’s excitement and material comforts.
Her relationships with men, first Drouet and then the wealthier Hurstwood, mark her transformation and rise, while also showing the potential costs of ambition. The novel depicts the allure and the dangers of the rapidly growing city.
Sam Greenlee wrote this sharp political thriller. Dan Freeman is recruited into the CIA as its token Black agent. After years of training in espionage and guerilla warfare, he leaves the agency.
He returns to Chicago and uses his skills to organize street gangs into a revolutionary force fighting against systemic racism and oppression. It’s a provocative story about power, race, and rebellion set against the backdrop of the city’s social landscape.
In this novella by Saul Bellow, Harry Trellman is a keen observer of people. He reflects on his life in Chicago, particularly his quiet love for Amy Wustrin. A wealthy acquaintance, Sigmund Adletsky, asks Harry for help regarding Amy.
This request forces Harry to confront his feelings and his place in the world. The story focuses on connections, memory, and understanding human behavior within the city environment.
V.I. Warshawski is back. While checking on an elderly client who is concerned about trespassers, V.I. discovers the body of a young Black journalist in the woman’s pond.
The investigation pulls V.I. into a dark chapter of Chicago history involving McCarthy-era blacklisting, old secrets, racism, and political corruption that still affects the present day.
This art mystery is for younger readers but enjoyable for adults too. Two Chicago sixth-graders, Calder Pillay and Petra Andalee, live near the University of Chicago. They become intrigued by the theft of a famous Vermeer painting.
Using pentomino puzzles, secret codes, and their knowledge of the Hyde Park neighborhood, they try to piece together clues about the crime and the artwork itself. Frank Lloyd Wright’s Robie House also plays a part.
Jim Butcher created Harry Dresden, Chicago’s only professional wizard listed in the phone book. He works as a private investigator who consults for the police on supernatural cases. This urban fantasy series blends detective noir with magic.
Harry deals with vampires, demons, faeries, werewolves, and other magical threats, often finding himself in over his head. The city of Chicago, from its underground tunnels to its landmarks, is a constant presence. The first book is Storm Front.
Richard Wright explores deep philosophical questions in this novel. Cross Damon feels trapped by his life in Chicago. When a subway accident gives him a chance to fake his death and escape, he takes it. He tries to live with complete freedom, unbound by morality or identity.
However, his journey leads him into violence and manipulation, questioning whether true freedom is possible or even desirable.
Joshua Ferris captures the absurdity and anxiety of modern office life. The story unfolds inside a Chicago advertising agency facing layoffs during an economic downturn.
Told from a collective “we” perspective, it follows the employees’ gossip, pranks, romances, and fears as they try to keep their jobs and navigate workplace dynamics. It’s funny and insightful about corporate culture.
Audrey Niffenegger wrote this unique love story set largely in Chicago. Henry DeTamble has a rare genetic disorder that causes him to involuntarily jump through time. Clare Abshire meets Henry throughout her life, but his appearances are out of order due to his condition.
Their relationship unfolds across decades, shaped by his unpredictable absences and reappearances. Familiar Chicago locations, like the Newberry Library where Henry works, ground their extraordinary story.
Marcus Sakey tells the story of Danny Carter. He’s a regular guy in Chicago with a good job and a girlfriend he loves. But years ago, he was involved in crime with his childhood best friend.
That friend gets out of prison and reappears in Danny’s life, threatening to expose his past and pull him back into violence. Danny has to decide how far he’ll go to protect the life he built.
This thriller blends crime and science fiction. Davis Moore is a fertility doctor in Chicago whose daughter is murdered. Years later, convinced the police have failed, he uses DNA evidence left at the scene and his expertise in cloning to create a clone of the killer.
He hopes that by raising the boy, he can understand the killer’s nature or perhaps even identify him when the clone reaches the same age. It raises fascinating questions about identity and fate.
Meyer Levin based this novel on the infamous Leopold and Loeb case from 1920s Chicago.
Two wealthy, intelligent university students, Judd Steiner and Artie Straus (fictionalized names), decide to commit the “perfect crime” – kidnapping and murdering a young boy – just to prove they can.
The story follows their planning, the act itself, the police investigation, and the sensational trial, offering a chilling look into their minds and the society they lived in.
Fredric Brown wrote this mystery novel that won an Edgar Award. Ed Hunter is eighteen when his father is murdered in a Chicago alley. Dissatisfied with the police investigation, Ed teams up with his uncle, Ambrose “Am” Hunter, a former carny worker.
Together, they delve into the city’s gritty underbelly, visiting bars (“clipjoints”) and encountering shady characters to find the truth. It’s a classic hardboiled story with a unique uncle-nephew dynamic.
Aleksandar Hemon intertwines two narratives. In 1908 Chicago, Lazarus Averbuch, a young Jewish immigrant and alleged anarchist, is shot and killed by the Chief of Police.
In the present day, Vladimir Brik, a Bosnian writer living in Chicago, becomes fascinated by Lazarus’s story. Brik receives a grant to travel to Eastern Europe, Lazarus’s homeland, to research the events.
The journey explores themes of immigration, identity, storytelling, and historical trauma. Actual historical photos are woven into the text.
This is another mystery featuring Calder, Petra, and also Tommy Segovia, set in their Hyde Park, Chicago neighborhood. Frank Lloyd Wright’s famous Robie House is scheduled to be dismantled and moved to museums.
The three kids believe the house holds secrets and hidden treasures related to Wright himself. They work together, using codes and observation skills, to try and save the house and uncover its mysteries before it’s too late.
Sandra Cisneros tells a sprawling family saga through the eyes of Celaya “Lala” Reyes. Each summer, her family makes an epic road trip from Chicago to Mexico City to visit the “Awful Grandmother.” Lala listens to family stories, secrets, and gossip.
She tries to piece together her own identity within this loud, loving, complicated Mexican-American family. A treasured striped caramelo rebozo (shawl) becomes a symbol connecting generations.
Part of the “Dear America” series, this historical novel is presented as the diary of eleven-year-old Nellie Lee Love. In 1919, after facing danger and racism in Tennessee, Nellie’s family moves north to Chicago as part of the Great Migration.
Nellie records her experiences adjusting to the city, facing new forms of prejudice but also finding opportunities and community. It offers a child’s perspective on this important period in American history.
Jacquelyn Mitchard’s novel became a huge bestseller (and an Oprah’s Book Club pick). Beth Cappadora takes her three young children to her high school reunion in Chicago. In a crowded hotel lobby, her three-year-old son, Ben, vanishes.
The story explores the devastating impact on the family over the next nine years – the grief, guilt, and strain on their relationships. Then, a boy who looks remarkably like Ben shows up in their neighborhood, leading to an emotional reckoning.
Richard Powers sets this story partly in Chicago. Russell Stone is teaching a creative writing night class when he meets Thassa Amzwar. Thassa, an Algerian immigrant, possesses an extraordinary, unshakeable happiness.
Her constant joy seems almost unnatural, attracting media attention and the interest of geneticists who wonder if they’ve found a “happiness gene.” The novel explores genetics, media, and the question of whether happiness should, or could, be engineered.
This young adult novel presents a stark scenario. A sudden plague kills everyone over the age of twelve. Lisa Nelson, a ten-year-old living near Chicago, finds herself responsible for her younger brother. Resourceful and determined, she scavenges for supplies.
She realizes survival depends on cooperation and defense, so she organizes the neighborhood kids, fortifies Glenbard High School, and forms a militia to protect their territory from other gangs. It’s a story about children forced to create their own society.
Valerie Taylor was an early writer of lesbian pulp fiction. This novel follows Barby, Annice, and Pat, three young women who leave their small hometowns for new lives in Chicago in the 1950s.
They share apartment 3-B and navigate work, independence, and relationships in the big city. The story touches on the challenges and freedoms women faced during that era, including explorations of sexuality that were rare for the time.
This is a fast-paced, witty crime novel from the 1930s. William Crane, a sophisticated private detective known for his drinking, is hired by a man on death row in Chicago’s Cook County Jail.
The condemned man, Robert Westland, insists he didn’t murder his wife and has only days before his execution to prove it. Crane races against time, interviewing suspects, dodging danger, and drinking his way through the city’s high society and underworld to find the real killer.
Another Bill Crane mystery set in Chicago. Detective Crane is sent to the city morgue to identify the body of a woman who supposedly committed suicide in her apartment. However, when he arrives, the body is missing.
Crane must track down the vanished corpse, plunging him into a convoluted case involving gangsters, blackmail, quirky characters, and more than a few cocktails. Latimer’s writing is known for its blend of suspense and dark humor.
Aleksandar Hemon tells the story of Jozef Pronek in a series of interconnected episodes. We see glimpses of his youth in Sarajevo, his experiences during the Bosnian War, a stint in Kyiv, and his eventual life as an immigrant in Chicago.
Pronek works various jobs (canvasser for Greenpeace, deli worker), observes American culture with an outsider’s eye, and tries to make sense of his displaced identity.
The book captures the feeling of being adrift between worlds, with Chicago as the backdrop for his American experience.