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Ten Great Books set in CHICAGO

17th August 2021

Chicago is the latest location for us to visit in our Great Books series. Ten Great Books set in Chicago. The city, on Lake Michigan in Illinois, is among the largest in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. The city is also renowned for its museums, including the Art Institute of Chicago with its noted Impressionist and Post-Impressionist works.

‘Let me tell you something. I’m from Chicago. I don’t break.’ – Barack Obama

Ten Great Books set in CHICAGOChicago: 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.

Deep Dark Night by Steph Broadribb

A city in darkness. A building in lockdown. A score that can only be settled in blood…

Working off the books for FBI Special Agent Alex Monroe, Florida bounty-hunter Lori Anderson and her partner, JT, head to Chicago. Their mission: to entrap the head of the Cabressa crime family. The bait: a priceless chess set that Cabressa is determined to add to his collection.

An exclusive high-stakes poker game is arranged in the penthouse suite of one of the city’s tallest buildings, with Lori holding the cards in an agreed arrangement to hand over the pieces, one by one. But, as night falls and the game plays out, stakes rise and tempers flare.

When a power failure plunges the city into darkness, the building goes into lockdown. But this isn’t an ordinary blackout, and the men around the poker table aren’t all who they say they are. Hostages are taken, old scores resurface and the players start to die.

And that’s just the beginning…

Ten Great Books set in CHICAGODisintegration by Richard Thomas

Once a suburban husband and father, now the man has lost all sense of time. He retains only a few keepsakes of his former life: a handmade dining room table, an armoire and dresser from the bedroom, and a tape of the last message his wife ever left on their answering machine. These are memories of a man who no longer exists. Booze and an affair with a beautiful woman provide little relief, with the only meaning left in his life coming from his assignments. An envelope slipped under the door of his apartment with the name and address of an unpunished evildoer. The unspoken directive to kill. And every time he does, he marks the occasion with a memento: a tattoo. He has a lot of tattoos.

But into this unchanging existence seep unsettling questions. How much of what he feels and sees can he trust? How much is a lie designed to control him? He will risk his own life—and the lives of everyone around him—to find out.

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.

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.

The Girl Next Door by Amy Jo Cousins

Charles “Cash” Carmichael traded his high-rise condo and family-firm career for a job coaching soccer for Chicago’s inner-city kids. He’s adjusting to living on minimum wage when his young cousin, newly out and running away from home, shows up on his less-than-luxurious doorstep.

Angsty teens definitely aren’t Cash’s thing. He needs local backup, and there’s only one name he can think of: Stephany Tyler. Back in the day, the bisexual Steph was the perfect friend with benefits until she fell in love with a woman.

To his relief, his former friend steps up to the plate. Soon, though, Cash finds himself feeling the familiar need to keep her in his bed, and in his life. But Steph, burned by the ex-girlfriend and by the absentee dad she’s been trying to connect with, won’t risk her heart again.

Good thing Cash believes in leaving it all on the field. If he can just convince Steph to get in the game, there’s a chance they can both win.

Building Stories by Chris Ware

In Chris Ware’s own words, ‘Building Stories follows the inhabitants of a three-flat Chicago apartment house: a thirty-year-old woman who has yet to find someone with whom to spend the rest of her life: a couple who wonder if they can bear each other’s company for another minute: and finally an elderly woman who never married and is the building’s landlady…’.

Ten Great Books set in CHICAGOThe House on Mango Street by Sandra Cisneros

A series of vignettes, rather than a structured novel, House on Mango Street is Sandra Cisneros’s semi-autobiographical account of growing up Chicana in a poor area of Chicago. Esperanza Cordero, at age eleven, has already discovered that being able to communicate in English is a key to worldly success, and she has begun recording stories of her neighborhood, friends, and everyday life, hoping one day to become a writer. Recreating one year of her life, she vividly depicts the children’s fierce loyalties to each other, their alienation from mainstream society, and their goals in life, sadly limited by the culture and its low expectations for girls and women.

The Litigators by John Grisham

David Zinc has it all: Big firm, big salary, life in the lawyer’s fast lane.

Until the day he snaps and throws it all away.

Leaving the world of corporate law far behind, he talks himself into a new job with Finley & Figg. A self-styled ’boutique’ firm with only two partners, Oscar Finley and Wally Figg are ambulance-chasing street lawyers who hustle nickel-and-dime cases, dreaming of landing the big win.

For all his Harvard Law Degree and five years with Chicago’s top firm, Zinc has never entered a courtroom, never helped a client who really needed a lawyer, never handled a gun.

All that is about to change..

Dead Land by Sara Paretsky

Chicago is the city of broad shoulders, but V.I. Warshawski knows its politics: “Pay to Play”. Money changes hands in the middle of the night; by morning, buildings and parks have been replaced by billion-dollar projects.

Private investigator V.I. gets pulled into one of these clandestine deals when her impetuous goddaughter Bernie tries to rescue a famed singer-songwriter, now living on the streets. Thanks to Bernie, V.I. finds herself in the path of some developers whose negotiating strategy is simple: they bulldoze – or kill – any obstacle in their way.

Questions pile up almost as fast as the dead bodies. When she tries to answer them, the detective finds a terrifying conspiracy stretching from Chicago’s parks to a cover-up of the dark chapters in the American government’s interference in South American politics. Before finds answer, V.I. will be pushed closed to breaking point. People who pay to play take no prisoners.

Any others you would like to add? Let us know in the Comments below…

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Enter the 2021TripFiction 'Sense of Place' Creative Writing Competition!

A story in which the location plays as important a role as the rest of your words.

2,500 word maximum, 750 word minimum

Judges include Victoria Hislop and Rosanna Ley

First Prize of £1,000 / US$1,350

Prizes total £1,750 / US$2,362 

Winning entry published on TripFiction site and publicised on Social Media

Entries close 6th November 2021