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Five great books set in Chicago

28th June 2019

Chicago is the latest destination in our ‘Great books set in…’ series. Five great books set in Chicago.

It is hopeless for the occasional visitor to try to keep up with Chicago-she outgrows his prophecies faster than he can make them. She is always a novelty; for she is never the Chicago you saw when you passed through the last time.” ―Mark Twain, Life On The Mississippi 1883

Here are five books that will transport you to this fascinating North American city, whether you’re travelling to Chicago, or just reading in your favourite comfy chair at home.

1. Chicago: A Novel by Brian Doyle

On the last day of summer, some years ago, a young college graduate moves to Chicago and rents a small apartment on the north side of the city, by the vast and muscular lake. This is the story of the five seasons he lives there, during which he meets gangsters, gamblers, policemen, a brave and garrulous bus driver, a cricket player, a librettist, his first girlfriend, a shy apartment manager, and many other riveting souls, not to mention a wise and personable dog of indeterminate breed.

A love letter to Chicago, the Great American City, and a wry account of a young man’s coming-of-age during the one summer in White Sox history when they had the best outfield in baseball, Brian Doyle’s Chicago is a novel that will plunge you into a city you will never forget, and may well wish to visit for the rest of your days.

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2. Noon in Paris, Eight in Chicago by Douglas Cowie

Sharp and intimate, Douglas Cowie’s reimagining of the turbulent love affair between Simone de Beauvoir and Nelson Algren asks what it means to love and be loved by the right person at the wrong time.

Chicago, 1947: on a freezing February night, France’s feminist icon Simone de Beauvoir calls up radical resident novelist Nelson Algren, asking him to show her around. After a whirlwind tour of dive bars, cabarets and the police lockup, the pair return to his apartment on Wabansia Avenue. Here, a passion is sparked that will last for the next two decades.

Their relationship intensifies during intoxicating months spent together in Paris and Chicago. But in between are long, anguished periods apart filled with competing desires lovers old and new, writing, politics, gambling which ultimately expose the fragility of their unconventional marriage and put their devotion to the test.

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3. Ramshackle by Elizabeth Reeder

Roe is like any other fifteen year old suburban Chicago teenager. Her only worries are schoolwork, keeping up with her wayward best friend, and whether or not she should sleep with her boyfriend.

Then her adoptive father, a locksmith, disappears one winter’s day without explanation. As Roe tries to find out where he is and why he left, her past unravels, revealing secrets and lies that will change her future forever.

This is a beautiful novel about loss, identity and self-discovery in the harshest of circumstances, set in suburban Chicago.

An extraordinarily assured debut.

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4. The Jungle by Upton Sinclair

Upton Sinclair’s dramatic and deeply moving story exposed the brutal conditions in the Chicago stockyards at the turn of the twentieth century and brought into sharp moral focus the appalling odds against which immigrants and other working people struggled for their share of the American Dream.

Denounced by the conservative press as an un-American libel on the meatpacking industry, and condemned for Sinclair’s unabashed promotion of Socialism and unionisation as a solution to the exploitation of workers, the book was championed by more progressive thinkers, including then President Theodore Roosevelt, and was a major catalyst to the passing of the Pure Food and Meat Inspection act, which has tremendous impact to this day.

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5. Native Son by Richard Wright

Set in Chicago, Illinois in the 1930s, Native Son is not a sugar-coated tale. It is a tale of a black man trapped by rules that pin him down, pen him in, force him to live in a certain (rat-infested) part of the city, make him only have certain kinds of (subservient) jobs, instill fear in him in every interaction in the wold of whites, and kill his ambitions (to be a pilot) because in the world he lives in, he will never realize those dreams.

Native Son is the story of crime and criminals, and specifically, the crimes of Bigger Thomas, who, because he is a black man, is deemed a criminal before he commits his first crime. In Native Son, Bigger Thomas is not a hero. He is not likeable. He commits atrocious acts, knowingly, and without remorse. But what’s fascinating about Native Son is the psychology of those crimes. The genius in Native Son is Wright’s ability to get us inside the mind and emotions of a poor black man who turns to crime because it is the only way he can truly be liberated — it is the only way he has control over his own life. Bigger is not admirable. The reader is not on his side. But he represents something bigger: what happens to humans when they are not free.

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Andrew for the TripFiction Team

Which titles would you add to the list? Remember there are others to choose from in the Chicago listings on TripFiction. Each will transport you to some excellent fiction, travelogues or memoirs set in this Great American City. Or you may have your own favourites you would like to add. Please leave your thoughts in the Comments box below.

Other US destinations in our ‘Five/ten great books set in…’ series include:

Ten great books set in New York

Five great books set in San Francisco

Five great books set in California

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  1. User: barbara baer

    Posted on: 28/06/2019 at 3:47 pm

    interesting list, thanks, Barb