In assembling my list of the top 40 Chicago novels, I have selected only those books that unfold at least partly in Chicago. That’s why you won’t find any of the award-winning novels—Larry Heinemann’s Paco’s Story, for instance—that were written here but set elsewhere. Nor will you encounter the great mythic figures birthed in Chicago: no Tarzan of the Apes, no Dorothy of Oz. Apologies to Edgar Rice Burroughs and L. Frank Baum, but residence here doesn’t guarantee entry to the list. (As for Ernest Hemingway, he essentially left Chicago behind in his early 20s and never looked back—which is why none of his works show up.) Books are ordered with an eye to their level of artistry, their long-term impact, and the extent to which they capture Chicago.

40. Barriers Burned Away
E. P. Roe (1872)
A historical curiosity, the first Chicago novel—a New York clergyman’s didactic tale about the great fire of 1871—served as the basis for a 1925 silent movie directed by W. S. Van Dyke.

39. Cooler by the Lake
Larry Heinemann (1992)
The jokes fall flat and the reviews were terrible, but this ostensibly comic novel, about a benign hustler named Maximilian Nutmeg, ably limns Chicago during the first term of the second Mayor Daley.

38. Presumed Innocent
Scott Turow (1987)
Before John Grisham, before Law & Order, Turow invented the modern legal procedural with this story of a Kindle (read “Cook”) County prosecutor charged with murdering his former mistress.

37. Letting Go
Philip Roth (1962)
The author’s first novel, coming three years after the National Book Award–winning Goodbye, Columbus (a novella), relates the travails of an academic at the University of Chicago, where Roth had also studied and taught.

36. The Moments Lost: A Midwest Pilgrim’s Progress
Bruce Olds (2007)
Having tackled the abolitionist John Brown and the gunfighter Doc Holliday in two earlier experimental novels, Olds took a more straightforward approach to his tale of a Chicago newsman, who, among other things, covers the deadly Iroquois Theatre fire of 1903.

35. Rebellion
Joseph Medill Patterson (1911)
A noted editor and publisher—his grandfather and father both ran the Chicago Tribune—Patterson centered his second novel on the long-suffering wife of a drunken ward heeler, who flouts public opinion and the Catholic faith to embrace her true love.

34. The Girls
Edna Ferber (1921)
Though most of her best-known works are set elsewhere—the Texas of Giant, the Mississippi River of Show Boat, the Broadway of Stage Door—Ferber, a Midwesterner, set this multigenerational tale in the city once called Che-ca-gou.

33. The Dean’s December
Saul Bellow (1982)
Against the backdrop of a murder trial, the politically incorrect Albert Corde (sitting in for the author) sets off a firestorm with a pair of essays upbraiding Chicago for its problems with race, class, and corruption.

32. The Song of the Lark
Willa Cather (1915)
A Colorado girl travels to Chicago, perfects her singing skills, and promptly decamps for the opera houses of New York and Europe—establishing a pattern followed all too often by subsequent generations of artists.

31. The Lazarus Project
Aleksandar Hemon (2008)
The author’s own status as a displaced immigrant gives a special resonance to this novel, half of which reimagines the 1908 killing—and subsequent investigation and cover-up—of a poor Russian-born Jew by Chicago’s police chief.

30. Windy McPherson’s Son
Sherwood Anderson (1916)
Best known for Winesburg, Ohio, Anderson set much of his first novel—about a newsboy who becomes an unscrupulous tycoon—in Chicago, where the author had realized his own artistic awakening.

29. I Sailed with Magellan
Stuart Dybek (2003)
As James Joyce is to Dublin, Dybek is to Chicago, and these interconnected stories, centered initially on the Little Village world of Perry Katzek, may be the closest we will ever get to a novel from one of the city’s finest writers.

28. Peel My Love Like an Onion
Ana Castillo (1999)
With cool Lake Michigan shimmering in the background, Carmen “La Coja” Santos, a crippled flamenco dancer, carries on two sizzling love affairs at once.

27. The House on Mango Street
Sandra Cisneros (1984)
Channeling her disillusionment into poetry, Esperanza Cordero plots to escape her home so that, paradoxically, she might one day return.

26. Hairstyles of the Damned
Joe Meno (2004)
Unfolding to the soundtrack of its own built-in playlist, this coming-of-age novel, set among the schools, homes, and shops of the Far Southwest Side, transcends its punk label to present a timeless tale of troubled adolescence.

25. The Rivers of Eros
Cyrus Colter (1972)
After 35 years, an adulterous liaison with her sister’s husband still haunts an African American woman—but did that indiscretion tragically curse three generations of her family?

24. The Odyssey of Kostas Volakis
Harry Mark Petrakis (1963)
In this 35-year saga that intermingles triumph and tragedy, Petrakis, the city’s Greek bard, relates the story of a young couple who exchange sun-kissed Crete for a Halsted Street restaurant.

23. The Old Bunch
Meyer Levin (1937)
Framed by snatches of song and references to Al Capone, Samuel Insull, and “Big Bill” Thompson, this bulky novel follows a dozen young second-generation Russian Jews from 1921 to 1934.

22. Maud Martha
Gwendolyn Brooks (1953)
In her only novel, the Pulitzer Prize–winning poet renders a commonplace life with the same lyricism that made her the state’s poet laureate.

21. Prairie Avenue
Arthur Meeker (1949)
Tarnished by the passage of time, Chicago’s most desirable Gilded Age address limps into the 20th century in this heartfelt tribute written by a former resident.

20. Knock on Any Door
Willard Motley (1947)
A onetime columnist for the Chicago Defender (where he wrote under the byline Bud Billiken), Motley, an African American, drew some criticism when he gave his first novel a white protagonist: Nick Romano, an altar boy gone bad. The book was later the basis for a Humphrey Bogart movie.

19. Erik Dorn
Ben Hecht (1921)
A restless journalist (not unlike the book’s author) bounces from a hectic Chicago newsroom to the chaos of postwar Berlin, along the way forsaking his wife, his mistress, and a German ingénue. This was the first novel by the legendary newsman, playwright, and Academy Award–winning screenwriter.

18. The Titan
Theodore Dreiser (1914)
Fresh from the penitentiary, Frank Cowperwood—a fictional rendering of the crooked mass-transit tycoon Charles Yerkes—brings his boodle-loving ways to Chicago in the second volume of Dreiser’s Trilogy of Desire.

17. Rose of Dutcher’s Cooly
Hamlin Garland (1895)
Remembered today for his Middle Border memoirs, Garland was also a prolific novelist; this story, about an ambitious Wisconsin farm girl—the novel’s eponymous hero—coming to adulthood in Chicago, was one of his best.

16. The Smiths
Janet Ayer Fairbank (1925)
A Civil War veteran and his wife forge a family and a fortune in the iron-and-steel business. Written by the sister of Margaret Ayer Barnes (number 11), the novel stretches from Lincoln’s funeral through the great fire of 1871 to the emergence of U.S. Steel.

15. The Memoirs of an American Citizen
Robert Herrick (1905)
A Harvard-educated professor at the University of Chicago, Herrick was never entirely comfortable with his adopted city for reasons laid out in this story of a devious meatpacker’s rise to the U.S. Senate.

14. With the Procession
Henry Blake Fuller (1894)
A wealthy, old-guard Chicago family makes a belated move to keep up with the city’s more noticeable newcomers in this fourth novel from the city’s first great man of letters.

13. Trumbull Park
Frank London Brown (1959)
Fed up with life in decrepit inner-city tenements, a group of African American families courageously integrates an all-white housing project on the Far South Side. The book was based on the actual experiences of the author, whose promising future was cut short by leukemia when he was only 34.

12. The Pit
Frank Norris (1903)
This second installment (after The Octopus) in Norris’s unfinished wheat trilogy zeroes in on the Chicago Board of Trade, the obsessive speculator Curtis Jadwin, and Laura Dearborn, the woman who becomes his wife.

11. Years of Grace
Margaret Ayer Barnes (1930)
A winner of the Pulitzer Prize and the best-selling novel of its time, this (unjustly) forgotten book covers 40 years in the privileged life of the Wards of Pine Street—later the commercially driven North Michigan Boulevard.

10. The Jungle
Upton Sinclair (1906)
Remembered now for spurring reforms in the country’s meatpacking industry, this account of the Chicago stockyards has a forgotten human side, embodied by the Lithuanian immigrant Jurgis Rudkus, who is nearly broken on the wheel of American capitalism.

9. Chin Music
James McManus (1985)
As Soviet missiles rocket toward Chicago, “Gamma” Ray Zajak, an amnesiac White Sox pitcher, endeavors to return to his family in this heartbreaking, virtuosic riff on The Odyssey.

8. The Man with the Golden Arm
Nelson Algren (1949)
A wounded vet and backsliding junkie, the card-dealing Frankie Machine inhabits Chicago’s seamy underside in this winner of the first National Book Award.

7. The Adventures of Augie March
Saul Bellow (1953)
With its unforgettable opening—“I am an American, Chicago born”—this barbaric yawp of a book introduces the city’s quintessential hero, a 20th-century Huck Finn. And like his literary predecessor, Augie insists on navigating the world on his own terms.

6. The Cliff-Dwellers
Henry Blake Fuller (1893)
Focusing on the denizens—aptly characterized by the book’s title—of the first skyscrapers, Fuller’s greatest novel unflinchingly portrays the newly emerging modern city and all the rapacious baggage trailing in its wake.

5. The Studs Lonigan Trilogy
James T. Farrell (1932–1935)
These three novels—Young Lonigan, the first, is the best—trace the career of a callow Irish Catholic street tough in Washington Park whose failure to recognize his deepest longings casts a tragic light on his tawdry tale.

4. Native Son
Richard Wright (1940)
Bigger Thomas, a brutish young African American on the South Side, battles—and tries to comprehend—the forces of racism and poverty that bind him. He ultimately stands trial for the accidental murder of a white woman in one of the first novels about the black experience to find a mass-market audience.

3. Sister Carrie
Theodore Dreiser (1900)
Sure, this novel famously kicked down the doors of convention—but it also offers a mesmerizing tale of corrupted innocence and besotted love set against a precisely drawn portrait of Chicago at the dawn of the 20th century.

2. Humboldt’s Gift
Saul Bellow (1975)
A lowlife gangster, a highbrow poet, and a vengeful ex-wife intersect in this tale of Charlie Citrine, a bewildered middle-aged man—and one of Bellow’s great protagonists—searching for his soul amid the detritus of America’s single-mindedly materialistic society. A winner of the Pulitzer Prize, the novel propelled Bellow to the Nobel Prize.

1. Divine Days
Leon Forrest (1992)
Although fictional Forest County stands in for Chicago, this novel still reigns as the city’s big-shouldered epic, when over eight days in February 1966, the would-be playwright Joubert Antoine Jones attempts to snare the spirit of the mythical Sugar-Groove. This modern masterpiece deserves to stand alongside the best of Pynchon and Joyce, as well as another great American novel: Moby-Dick.