The Sombre City: The Top Ten Chicago Novels

Chicago is a uniquely American city; an inclusive melting pot perched on the edge of the Midwestern desert, it has proved to be a tantalising prospect for novelists seeking to define and elaborate the profundities of American life.

Chicago at Night

Chicago has provided ample inspiration for a wide array of writers over the decades; its distinctive blend of Midwestern suburban sprawl and Gothamesque cityscape making it a potent symbol of American urban existence. Its all-encompassing capaciousness makes it a perfect foundation for the novel form and many writers have turned to the windy city to give substance to their works. This by no means exhaustive list seeks to outline some of the best the city’s writers have offered.

Willa Cather

Willa Cather – The Song of the Lark

A story of a young girls travails as she moves from the Midwestern country side to Chicago and finds fame as a singer in the metropolis. Cather’s novel is a typical tale of a young woman finding her way in the world made distinctive by its evocation of Chicago life in the early Twentieth Century

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Letting Go

Philip Roth – Letting Go

The first full length novel by a giant of American literature, Roth’s Letting Go is a depiction of the paralysing constraints of 1950s society and the tension between academic idealism and corporeal pleasure, all set to the backdrop of the University of Chicago.

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Upton Sinclair

Upton Sinclair - The Jungle

A tale of corruption and revulsion in Chicago’s meat packing industry; this novel was so successful that it prompted new legislation of the industry. It remains relevant as an excoriating attack on capitalism and the exploitation of workers.

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Henry Blake Fuller


Henry Blake Fuller - The Cliff Dwellers

Depicting the early years of the city, Henry Blake Fuller’s novel is a testament to the rapid spread of the Chicago metropolis. It is also a prescient portrayal of the psychological implications of a typically cramped urban existence.

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Humboldt's Gift

Saul Bellow - Humbolt’s Gift

The prototypical Chicago novelist, almost all of Bellow’s works have some relation to the city in which he grew up. Humbolt’s Gift is an interrogation of the commodification of high culture in American, as well as a depiction of the Chicago underbelly.

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The House on Mango Street

Sanda Cisneros - The House on Mango Street

A portrayal of the ‘Chicano’ society in Chicago; the community of Mexican and Puerto Ricans immigrants living in the city’s slums, Cisneros’s novel is notable because of its innovative approach to the depiction of community life.

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Nelson Algren

Nelson Algren - The Man with the Golden Arm

Controversial for its time, Algren’s novel recounts the travails of the lowlife drug addicts and small time crooks who populate Chicago’s north side ghettos in the years following World War II.

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Theodore Dreiser

Theodore Dreiser - Sister Carrie

A depiction of turn of the century urban life and the changes that such a frenetic existence brought to personal relations, Dreiser’s novel reveals the way in which Victorian morality and values crumbled in the face of city existence and capitalist greed.

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Richard Wright

Richard Wright - Native Son

One of the most powerful realisations of the African-American experience in fiction, Wright’s novel is a profound interrogation of the ways in which black Americans were forced to succumb to the dominant stereotypes created by white society to define their identity.

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The Adventures of Augie March

Saul Bellow - The Adventures of Augie March

Another work by Bellow which takes Chicago as its subject, The Adventures of Augie March depicts the life of a young man struggling to define his identity in the metropolitan sprawl. Its opening lines set out its stall as both an American novel and a Chicago novel: ‘I am an American, Chicago born—Chicago, that sombre city—and go at things as I have taught myself…’

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By Thomas Storey


Images courtesy: 1: Lol19/WikiCommons, 2: Carl Van Vechten/WikiCommons, 3: Letting Go/WikiCommons, 4: Time Magazine/WikiCommons, 5: Joseph Dimuro/WikiCommons, 6: Humboldt's Gift/WikiCommons, 7: The House on Mango Street/WikiCommons, 8: Albertin Walter/WikiCommons, 9: Carl Van Vechten/WikiCommons, 10: Carl Van Vechten/WikiCommons, 11: The Adventures of Augie March/WikiCommons.

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