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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.
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.
Photograph: Megan Lovejoy