Old Blue Eyes himself, Frank Sinatra, famously recorded the hit song that declared, “Chicago is my kind of town!” He’s not the only one to have fallen in love with the Windy City over the years. On the banks of Lake Michigan with the Chicago River running through it, the city is one of the most beloved in the United States, if not the world.
Chicago has inspired movies, musicals, television shows, art, and, of course, legions of die-hard Chicago sports fans. It has also inspired quite a bit of fantastic literature. Many great books published in the last few decades are set in Chicago. These books vary from thrillers to romance to true crime, but all have one thing in common: they all use the City of Chicago itself as a character.
On this list of some of the best books ever to be set in Chicago, we will look at the best works of fiction that take place in the Second City. The books are listed in chronological order and span the last 30 or so years, from 1987 to 2018. Here are the top 14 awesome books set in Chicago.
1. Presumed Innocent by Scott Turow (1987)
- GRAND CENTRAL
This is the first novel written by one of the masters of legal thrillers, Scott Turow. This book, and his 10 novels and 2 non-fiction tomes that followed, have sold over 30 million copies worldwide and are available in over 40 languages. Turow wrote this book in 1987 after he left his career as a lawyer.
Presumed Innocent is the first of Turow’s series of 11 legal thrillers set in the fictional, Midwestern, Kindle County. Turow uses Kindle County as a stand-in for Cook County, the county in which Chicago is situated. The book is about Rusty Sabich, a prosecutor for the Kindle County District Attorney’s office, who is assigned to investigate the gruesome and kinky murder of his colleague, Carolyn Polhemus.
Rusty accepts the assignment, even though he has a conflict of interest, due to the fact that he had an affair with Carolyn prior to her murder. As Rusty starts to investigate, he becomes the prime suspect. Rusty is put on trial for the murder as the twists continue. Evidence goes missing, the judge has a secret past, and Rusty starts to look like he may be the killer after all. This book is the first of Turow’s page-turners and shows how he became a legend in the genre.
It is no surprise that Turow uses a fictional version of Cook county to set his novels. Born in Chicago, Turow left for college and Harvard Law School in his late teens, but eventually returned to the city to become the Assistant U.S. Attorney in Chicago before becoming a full-time author. He prosecuted some high-profile cases in his time as Assistant U.S. Attorney and much of the insight he gained found its way into his novels.
2. Divine Days by Leon Forrest (1992)
- Used Book in Good Condition
Leon Forrest is a Chicago-born and raised author who is one of the most prominent African-American writers from the city. Forrest attended Park High School, Wilson Junior College, Roosevelt University, and The University of Chicago before joining the military. When he returned in 1973, he became a professor at Northwestern University. He wrote four novels and had 2 posthumously published collections of stories. In 2013, he was inducted into the Chicago Literary Hall of Fame.
Divine Days was the last book Forrest wrote and is an epic story based on James Joyce’s Ulysses. Critics have compared the 1,000-plus page book to an African-American version of Tolstoy’s War and Peace. The plot follows the main character, Joubert Jones, an aspiring playwright. When we meet Jones, he is working to make ends meet by bartending at his Aunt Eloise’s Night Lounge. The book goes on to tell the story of seven days in Jones’ life as he meets and interacts with a rich cast of characters who help to illustrate what life is like for black people in America.
The book is set in the mid-1960s in Chicago and is semi-autobiographical about the Chicago Forrest found when he returned from military service. His lead character, Jones, is trying to finish his play, with the same name as this novel, about a missing, almost mythical Chicago character, Sugar Groove. The week-in-the-life story paints an amazingly vivid picture of what it was like for a black man to return to the U.S. in the 60s and deal with all the good and the bad that was going on in its major cities at that time.
3. The Devil in the White City by Erik Larson (2002)
The Devil in the White City: Murder, Magic, and Madness at the Fair That Changed America
- Chicago Exposition
- Nineteenth Century
- True Crime
- Serial Killer
One of the few books on this list not written by a native Chicagoan, The Devil in the White City is a novelized version of a true-crime event series that took place in Chicago in 1893. Written by journalist (and New Yorker) Erik Larson, the book has won numerous awards and also had a long run on the New York Times bestseller list.
The book reports on a series of murders around the time of the 1893 World’s Columbian Exposition in Chicago. The characters and events in the book are real but Larson writes the book like a novel. The story is mostly told from the point of view of one of the designers of the Fair, Daniel Burnham, and is about the crimes of H. H. Holmes. Holmes was a criminal and conman who used his World’s Fair Hotel, later nicknamed “The Murder Castle” in the late 19th century to murder multiple people. Holmes’ actions have led him to be considered the first modern serial killer.
The narrative of the book goes back and forth between Burnham struggling to pull together the massive undertaking of the World’s Fair and Holmes planning to murder people who are drawn to the event. In addition to taking place at this historic Chicago venue, some parts of the book are set in Philadelphia a few years later.
The rights to turn the book into a film were bought by Oscar-winning actor Leonardo DiCaprio in 2010. While the original plan was to turn the book into a film directed by legendary director Martin Scorsese, in 2019, DiCaprio and Scorsese instead began executive producing a streaming series based on the book.
4. 47th Street Black by Bayo Ojikutu (2003)
47th Street Black: A Novel
- Used Book in Good Condition
When your first book wins multiple prizes such as the Washington Prize for Fiction and the Great American Book Award, you know you are in for a great writing career. This is exactly what happened to the Nigerian-born Chicago native Bayo Ojikutu.
This is another set-in-Chicago book that also tells the tale of African-Americans in the city in the 1960s. Unlike Leon Forrest’s epic, though, this book is a straight gangster tale of crime and revenge.
The book focuses on two friends of Chicago’s Southside, Mookie and JC. When the two find a dead body, it puts them on a path that sees them start to work for the Southside’s most notorious gangster. The two friends quickly become flashy, notorious gangsters themselves but that path ultimately leads to 15 years in jail for JC. When he gets out, Mookie is now in charge of the old neighborhood and it is going to be harder than JC ever imagined to get to him to take his revenge.
The book had been praised for Ojikutu’s rich and nuanced writing and his development of both the characters and Chicago. This should come as no surprise as Ojikutu is not only a writer himself but a professor of creative writing who has taught at legendary Chicago-area institutions such as The University of Chicago, DePaul University, and Roosevelt University.
For those who enjoy Ojikutu’s book about Chicago back in the day, they can check out his second novel, Free Burning, which is also set in Chicago. This is a more modern tale about a young Chicagoan who loses his job and must navigate the mean streets of the city.
5. The Time Traveler’s Wife by Audrey Niffenegger (2003)
Her Fearful Symmetry
- Audrey Niffenegger
One of the most popular books to be set in Chicago in the last 30 years is The Time Traveler’s Wife by Audrey Niffenegger. The book has sold millions of copies worldwide and was made into a hit 2009 movie starring Racheal McAdams and Eric Bana. It is scheduled to be an upcoming HBO series.
The story is part science fiction and part romance novel but it stays grounded in the real world thanks to Niffenegger’s vivid description of her and her characters’ hometown of Chicago. The plot is about a woman, Claire Anne Abshire, whose husband, Henry DeTamble, experiences a condition where he abruptly and unexpectedly travels through time. The wife, who is an artist, has a hard time dealing with her husband’s unexpected absences and the dangerous experiences he deals with while time-hopping.
The book is semi-autobiographical for Niffenegger who is an artist based in Chicago just like her main character. She has said in interviews that the plot of the book is based on her dating history and failed relationships. She has been working on a sequel to this book, supposedly titled The Other Husband, but as of 2020, the book is yet to be released.
This book and author has an interesting connection to the first book on this list. One of the big moments that propelled this book to become an international sensation was when fellow author, Chicagoan, and family friend Scott Turow mentioned the book on The Today Show.
6. I Sailed with Magellan by Stuart Dybek (2003)
I Sailed with Magellan
|Is Adult Product|
|Number Of Pages||324|
Stuart Dybek is a born and raised Chicago author and poet who has written and published a number of collections of poetry and short stories. Dybek is known as one of the great chroniclers of the urban streets of Chicago where he came of age as the second-generation son of Polish immigrants.
Similar to Dybek’s own background, I Sailed with Magellan follows the life and times of Perry Katzek, a young Polish-American growing up on Chicago’s Southwest Side. The book is set in the 1950s and 1960s and follows Perry as he navigates the streets of Chicago where, as the book jacket says, he encounters “butchers, hitmen, mothers and factory workers, boys turned men and men turned to urban myth.”
The book is written in an interesting format. It is a novel written in parts and is actually 11 different stories. These stories are interconnected by the fact that they all feature Perry and are told from his point of view. They span two decades and take the reader all over the ethnically segregated neighborhoods that formed the melting pot of mid-20th century Chicago.
Dybek uses the Windy City as a backdrop in much of his work. One of his earlier collections of short stories, The Coast of Chicago is considered one of the best collections about the city and won numerous awards. It was chosen as a New York Times Notable Book and also an American Library Association Notable Book in 2005.
7. Hairstyles of the Damned by Joe Meno (2004)
Hairstyles of the Damned (Punk Planet Books)
- Used Book in Good Condition
The only author with 2 different novels on his list is Joe Meno who has been writing novels set in Chicago since he was 24-years-old. He has found success with a DIY ethic similar to the bands who make the punk music he so frequently writes about in his books. This book was released by Punk Planet Books, the publishing arm of the small, independent, Chicago-based punk music zine for which Meno has also written.
This is a classic coming-of-age tale that follows high school punk, Brian Oswald, as he navigates his sophomore and junior year at a Catholic high school on Chicago’s South Side. The story and its setting are very close to Meno’s adolescent period. In this world, Brian encounters many outcasts, deals with his parents’ divorce, finds a burgeoning punk scene, and tries to come to terms with the racism he sees in his town and his school. He experiences relationships and heartbreak and ultimately figures out that everyone in his world is simply trying to find their identity.
Meno has won awards for his writing and this book specifically got him included on the Barnes & Noble Discover Great New Writers list for 2004-2005. This title was a departure from his earlier books that were released by larger, more traditional publishers. Meno has railed against these types of publishers in interviews saying that they are scared to take chances on riskier material. This complaint includes his books which sometimes include profanity, drugs, violence, and other racy, taboo topics.
8. Water for Elephants by Sara Gruen (2006)
Water for Elephants: A Novel
- Algonquin Books of Chapel Hill
Author Sara Gruen is one of the rare authors on this list not from Chicago and, in fact, is not even from the U.S. Gruen hails from Vancouver, British Columbia in Canada although she moved to the U.S. in her 20s and currently resides in North Carolina. Her smash-hit book, Water of Elephants has Chicago ties.
The protagonist of the book, Jacob Jankowski is a 93-year-old man in a nursing home at the beginning of the book. The plot follows his retelling of his unique life story. As a college student, his parents are tragically killed in a car accident which sets him on a path to become a circus vet. With the circus, Jacob encounters a host of interesting characters including August, a sadistic animal trainer, and his wife Marlena with whom Jacob falls in love.
The story mainly covers the events with the circus when Jacob is in his 20s, but the end of the book briefly goes through the events that led him to the nursing home in Chicago where he is today. It is revealed that after he left circus life, he made his career as the chief veterinarian at the Brookfield Zoo in Chicago.
The book became a New York Times bestseller in 2007 and stayed on the list for 12 weeks, peaking at #7. A year later, when the paperback came out, the book had gained momentum and made it all the way to #1 on the prestigious NYT paperback bestseller list. Due to this monstrous level of popularity, the book was turned into a movie.
The 2011 movie with the same name as the novel was a big-budget production. It starred Reese Witherspoon, Robert Pattinson, Hal Holbrook, and Christoph Waltz and was directed by Hunger Games director, Francis Lawrence. The film was a modest box office success and was generally well-reviewed by critics.
9. The Fifth Floor by Michael Harvey (2008)
The Fifth Floor: A Michael Kelley Novel (Michael Kelly Series)
|Number Of Pages||288|
Michael Harvey is the creator of the Michael Kelly series of crime novels that are some of the best hard-boiled private eye books to be set in the City of Big Shoulders. Harvey’s crime novels, whether in the Michael Kelly series or not, have been compared favorably to some of the masters of the genre such as Dennis Lehane.
This is the second of five Michael Kelly books which include other titles such as The Chicago Way, The Third Rail, We All Fall Down, and The Governor’s Wife. The plot follows Michael Kelly, an ex-cop turned PI who is hired, at the beginning of the book, by an ex-girlfriend to investigate her abusive husband. The investigation turns out to be more than Kelly bargained for. The case takes him from the gritty streets of Chicago’s North Side all the way to the fifth floor of City Hall where the Mayor’s office is located.
Harvey is not originally from Chicago (he grew up in the Boston area) but after receiving a Master’s Degree from Northwestern University, he settled in the Jewel of the Midwest. He is an adjunct professor at Northwestern’s Medill School of Journalism and owns an Irish pub in the city known as The Hidden Shamrock. He is now such an ingrained part of the Chicago literary scene that in 2011, the Chicago Tribune named him the “Chicagoan of the Year” in Literature.
In addition to writing novels, Harvey has a background in investigative journalism focusing on police work. This specialty led him to become the co-creator and executive producer of A&E’s hit forensic television series, Cold Case Files. He has been nominated for Emmys in this capacity.
10. The Lazarus Project by Aleksandar Hemon (2008)
The Lazarus Project
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Like the modern-day protagonist of this novel, which jumps back and forth between 1908 and a modern-day storyline, Alexander Hemon is a Bosnian-born writer who relocated to Chicago. He came to the States in the 90s from his war-torn country knowing little English and became a popular English-language author. This incredible transition earned him the 2003 MacArthur genius grant.
This book jumps between the present-day, where Brik, a writer from Eastern Europe who is living in Chicago becomes obsessed with telling the (true) life-and-times story of another young Chicago-based immigrant Lazarus Averbuch, the title character. These two periods begin to mirror each other as a way to illustrate the similarity of the immigrant experience in America throughout history.
The present-day story sees Brik get obsessed with Lazarus and travel back to Sarajevo with his friend and photographer Rora. The 1908 story involves Lazarus, a Jewish immigrant who visited the Chicago Chief of Police, George Shippy, and wound up dead. There are differing reports about what happened but the incident stoked the built-up tensions between long-term Chicagoans and the immigrants of the day which started in earnest during the Haymarket Affair a decade earlier.
The story Is a great example of how Hemon compares and contrasts the experience of immigrants at the beginning of the 20th century with those at the beginning of the 21st century. Hemon postulates through his characters that as much as it seems like Chicago and the world at large has changed, many things have stayed exactly the same.
11. The Great Perhaps by Joe Meno (2009)
The Great Perhaps: A Novel
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|Number Of Pages||414|
This is the second entry on this list from 46-year-old, Chicago-based author Joe Meno. This book, written five years after Hairstyles of the Damned, shares some of the same themes as that book but expands on them. It is another coming of age tale but this time, it focuses on an entire Chicago family coming of age together and apart.
This book marked Meno’s return to a major publishing house. After finding success with Hairstyles of the Damned and the follow-up, The Boy Detective Fails, with an indie publisher, Meno got a deal with New York-based publisher W.W. Norton for this 2009 novel. The book found a good measure of success, won the Great Lakes Book Award for Fiction in 2009 and was named a New York Times Book Review Editor’s Choice.
The story of this book concerns a Chicago family where each member is struggling in their own way. The father, Jonathan, is a paleontologist looking for and not finding the giant squid he seeks. His wife, Madeline, is a scientist who cannot figure out why her experiments with animals are not working. Daughters Amelia and Thisbe are courting revolution and God, respectively, and their grandfather, Henry, is trying to shut down his life and leave the world.
When Jonathan and Madeline decide to divorce, the family is thrust into crisis and out of their comfort zones where they are allowed to indulge in their own pursuits. Eventually, what they each realize is that the thing for which they each search is really about their own cowardice.
12. Divergent Series by Veronica Roth (2011-2018)
Divergent Series Four-Book Paperback Box Set: Divergent, Insurgent, Allegiant, Four
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- Katherine Tegen Books
At only 32 years of age, Veronica Roth, a Northwestern alum who grew up in the Cook County suburbs, has written a trilogy of novels that have become one of the most popular Young Adult (YA) series since the Hunger Games. The series has sold millions of copies worldwide and was turned into a trilogy of big-budget movies as well.
Roth wrote the first book in the series, Divergent, as a senior at Northwestern. The book was published in 2011. She followed that up with Insurgent in 2012 and Allegiant in 2013. In 2014, Roth released a collection of short stories set in the Divergent Universe entitled, Four: A Divergent Collection.
The Divergent series is set in the Divergent Universe where society is divided into five separate factions in a post-apocalyptic Chicago. The main character, Beatrice (Tris) Prior goes from one faction to another and must hide her true identity from her new societal niche or risk being killed by the leaders of the faction.
Tris begins a romance with another teen who transferred between two factions, Tobias Easton. Together, Tris and Tobias begin to search for meaning in this dystopian world and find a conspiracy that, if exposed, will throw off the balance of the whole world and plunge the entire system into chaos.
The books were made into a movie trilogy that was released between 2014 and 2016. These films sported an all-star cast with Shailene Woodley and Theo James in the lead roles, along with Ansel Elgort, Zoë Kravitz, Miles Teller, and Kate Winslet playing lesser characters. Even though the movies were not loved by critics, the trilogy made over $750 million worldwide.
13. The Nix by Nathan Hill (2016)
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- NOVEL ,BOOK PAPERBACK, NEW YORK BEST SELLER, THE NIX, NATHAN HILL,
Nathan Hill was born in Cedar Rapids, IA but frequently moved throughout the Midwest while growing up. His debut novel, The Nix, shares his place-hopping experience and is not only set in Chicago but takes us on a journey throughout the Midwest, to New York City, and even as far away as Norway. This novel develops as good a sense of place as any of the Chicago books on this list, it just happens to do this on a journey as opposed to in a static location.
The plot concerns Samuel Andresen-Anderson, a blocked writer, bored college professor and an online gamer, whose world is turned upside down when his estranged mother appears on the news one day throwing rocks at a presidential candidate. Samuel thinks she never left the small town where he grew up, but the media paints her as a wild, political radical. This sets Samuel on a quest to find out who his mother really is.
This journey takes him from the cornfields of the Midwest to the tumultuous 1968 Democratic National Convention in Chicago to the Occupy Wall Street movement in New York City and, in the end, to Norway where Samuel goes in search of the mysterious Nix that his mother told him stories about.
The novel is an epic one, with almost 700 pages. It is written with depth and humor and is often compared to the work of the highly-regarded author Jonathan Franzen. The book is broken into 10 parts and is an interesting portrait of the history of America and the people who have fought for change.
14. The Great Believers by Rebecca Makkai (2018)
The Great Believers: A Novel
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|Number Of Pages||448|
Following the success of her first two novels, The Borrower in 2011 and The Hundred-Year House in 2014, author Rebecca Makkai published her latest work, The Great Believers in 2018. The book was critically acclaimed and included on a host of “best of” lists in 2018 including The New York Times Best 10 Books of the Year list, the Washington Post Notable Books list, and the New York Public Library’s 2018 Best Books list.
On this list, we have had books set in Chicago in the 60s, 70s, 90s, throughout the 21st century, and even in post-apocalyptic Chicago. This one takes a look at Chicago in the fascinating and tumultuous decade of the 1980s. Specifically, it tells the tale of the burgeoning AIDS epidemic at that time. The AIDS story has been told many times, in many big books and movies but almost always set on the east or west coast. This tells a story about the early days of this brutal disease from a Midwestern point of view.
The book tells two interwoven stories and jumps between two timelines. One is based in 1980s Chicago where Yale, an art dealer, is dealing with the AIDS epidemic and watching many of his friends dying around him. He ends up becoming very close with his friend Nico’s younger sister, Fiona.
In the second timeline, Fiona is in modern-day Paris searching for her daughter who may have joined a cult. When a friend in Paris’ old photos remind her of that time in 1980s Chicago, she is forced to deal with her past and how the AIDS epidemic has shaped her present and future.