5 Essential Chicago's Books [5 Best Books]

We chose books that covered not only the state’s 200-year history, but its 450-mile length. Doing so helped me understand how complicated Illinois really is. The state’s most experimental modernist novelists aren’t from Chicago, they’re from Herrin (Robert Coover) and Champaign (David Foster Wallace). And its best immigrant novel is by an Ethiopian who arrived in Peoria at age two, Dinaw Mengistu. Fiction, poetry and history are the best guidebooks.

*****

Spoon River Anthology, Edgar Lee Masters

Edgar Lee Masters put the Spoon River on the map. Of course, it’s on the cartographic map, flowing for 145 miles between Kewanee and Havana, but no one outside west-central Illinois would know its name if Masters hadn’t applied it to his collection of small-town epitaphs.

A native of Lewistown who made his living as a Chicago lawyer, Masters conceived his work as a series of posthumous remembrances by inhabitants of a graveyard who are all “sleeping, sleeping, sleeping on the hill.” Franklin Jones could have finished his flying machine and become rich and famous “If I could have lived another year.” Margaret Fuller Slack was wooed by a druggist who promised her “leisure for my novel,” then bore eight children, leaving her no time to write, and the conviction that “Sex is the curse of life!” As a young maid, Elsa Wertman was seduced by her employer. The family adopted her baby. He became a prominent politician who was never aware that his real mother was listening to his speeches, wanting to cry, “That’s my son!” The human disease of ambition survives even death. All the sleepers have eternity to regret how they spent their short time among the living, and thanks to Masters’s poetic art, their stories are still read more than a century later.

The Song of the Lark, Willa Cather

In the early 20th Century, Chicago—America’s fastest-growing city—was the place to set a realist novel. Theodore Dreiser did it with Sister Carrie, Upton Sinclair did it with The Jungle, and Willa Cather, the greatest novelist of that age, did it with The Song of the Lark, the story of Thea Kronborg, an aspiring pianist who leaves her small town in Colorado to study music in Chicago. Not even Chicago is big enough for Thea’s talent. In an age-old story, after serving her apprenticeship there, Thea moves on to New York, where she sings at the Metropolitan Opera. Another Chicago connection: the novel’s title was inspired by the painting of the same name by Jules Breton, which hangs in the Art Institute.

A Street in Bronzeville, Gwendolyn Brooks

There may be more widely read Chicago authors than Gwendolyn Brooks, but there has never been one more beloved. “Miss Brooks,” as the poetess was known (although she was married to Henry Blakely for 57 years) succeeded the Olympian Carl Sandburg as Illinois Poet Laureate. Brooks’s first collection, A Street in Bronzeville, offered a more commonplace look at Black Belt life than Wright’s drama. The lead-off poem is titled “kitchenette building”: “‘Dream’ makes a giddy sound, not strong/ Like “rent,” “feeding a wife,” “satisfying a man.” Brooks was an inspiration to the city’s rappers, and even in this early work, Brooks’s verses contain the seeds of hip-hop, as when she writes about “the soft man”: “Disgusting, isn’t it, dealing out the damns/ To every comer? Hits the heart like pain./ And calling women (Marys) chicks and broads/ Men hep, and cats, or corny to the jive.”

Five years later, Brooks became the first African-American to win a Pulitzer Prize, for Annie Allen. A statue of Brooks was recently unveiled in a Kenwood park that bears her name.

The Man with the Golden Arm, Nelson Algren

Wicker Park sure has changed since Nelson Algren lived and wrote there. Just after World War II, when The Man with the Golden Arm takes place, it was a Polish neighborhood of run-down three-flats and even more run down taverns. Frankie Machine returned from the war with a morphine habit – a “monkey on his back,” a term Algren heard among the hustlers and junkies on Division Street, and introduced to the popular vernacular in this novel. Unable to work as a musician due to his addiction, Frankie deals cards in backroom poker games, hence the title. Algren, who began his career during the Depression, was the last of the proletarian novelists, still writing about the urban underclass at a time when Americans were moving to the suburbs.

The Man with the Golden Arm won the first National Book Award, but Algren’s career went into a long decline afterwards, until he finally moved to Paterson, New Jersey, in the 1970s, to research a book on boxer Ruben “Hurricane” Carter. Nonetheless, he is considered the Great Chicago Novelist, namesake of a fountain at Division and Milwaukee, and of the Chicago Tribune’s annual fiction contest.

Bloody Williamson, Paul M. Angle

The Herrin Massacre was the deadliest incident of labor violence in Illinois’s history, with more casualties than the Haymarket Bombing or the Republic Steel Massacre. On June 22, 1922, striking coal miners captured 50 scabs from Chicago at a strip mine, and ordered them to run for their lives toward Herrin. On the road back to town, 18 hapless strikebreakers were shot or stabbed to death. Their killers were acquitted by sympathetic local juries. That was only one chapter in Williamson County’s tumultuous 1920s, which also included a Ku Klux Klan war for control of the county, and shootouts between bootleggers. Angle, director of the Chicago Historical Society from 1945 to 1965, makes the case that Southern Illinois’s culture, with its penchant for feuds and suspicion of outsiders, never strayed far from that of the upcountry Kentuckians and Tennesseeans who settled the region.