When you’re looking for a good novel about Chicago, you’re most likely to turn to those writers identified as Chicago writers, such as Saul Bellow (The Adventures of Augie March), Sara Paretsky (Indemnity Only), Richard Wright (Native Son), or Joe Meno (Hairstyles of the Damned).
But there are some fine Chicago novels by writers who aren’t identified closely with the city, such as Philip Roth, Thomas Pynchon, and others. Here are six of them, with excerpts:
Letting Go (1961) by Philip Roth—Throughout his half-century career as a novelist and short story writer, Roth almost always set his fiction in his birthplace of New Jersey. But in this, his first novel, he has his characters move around 1950s Chicago, New York, and Iowa. An excerpt:
“He spent the darkening hours of the afternoon walking out of one store and into another, through the blowy Loop and then straight into the wind up Michigan Boulevard — most of the time with no idea of what he was after….
“Parked at the curb was the little beat-up convertible that he knew she had bought for herself; the bumpers were crusty and one door wasn’t shut tight. He saw her remove her walled from her purse. She handed a bill to the Negro—and traffic was moving again, horns blowing down his neck. But he did not start forward—he couldn’t. A train overhead drove down on the piles of the el with all its force. An equivalent force drove down on him.”
Lucy Gayheart (1935) by Willa Cather—In American literature, Cather is best known for her novels of frontier life on the Great Plains, such as O Pioneers! (1913) and My Ántonia (1918). Lucy Gayheart is an existential novel that alternates between Lucy’s piano studies in Chicago and her visits back home to Haverford, NE. An excerpt:
“Lucy carried in her mind a very individual map of Chicago: a blur of smoke and wind and noise, with flashes of blue water, and certain clear outlines rising from the confusion; a high building on Michigan Avenue when Sebastian had his studio—the stretch of park where he sometimes walked in the afternoon — the Cathedral door out of which she had seen him come one morning — the concert hall where she first heard him sing.
“This city of feeling rose out of the city of fact like a definite composition, — beautiful because the rest was blotted out. She thought of the steps leading down from the Art Museum as perpetually flooded with orange-red sunlight; they had been like that one stormy November afternoon when Sebastian came out of the building at five o’clock and stopped beside one of the bronze lions to turn up the collar of his overcoat, light a cigarette, and look vaguely up and down the avenue before he hailed a cab and drove away.”
Against the Day (2006) by Thomas Pynchon—Pynchon is a huge figure in American letters, tacking a vast range of subjects and genres and influencing such younger writers as David Foster Wallace, Richard Powers, David Mitchell, Dave Eggers, Don DeLillo, Salman Rushdie, Laurie Anderson, Paul Thomas Anderson, and T. Coraghessan Boyle. The action in Against the Day takes place between the 1893 Chicago World’s Fair and the time immediately following World War I. An excerpt:
“Through the winter, though it seemed like any Chicago winter, that is as sub-zero-degrees version of hell, Lew lived as economically as possible….Out the window in the distance, contradicting the prairie, a mirage of downtown Chicago ascended to a kind of lurid acropolis, its light as if from nightly immolation warped to the red end of the spectrum, smoldering as if always just about to explode into open flames.
Diversey (1928) by MacKinlay Kantor—Although little-known today, Kantor was one of the most successful novelists and magazine writers in mid-20th century America, churning out bestsellers, including the Civil War novel Andersonville (1955), winner of the Pulitzer Prize. In 1928, he was living in Chicago when he published Diversey as his first novel, with a story centered on a rooming house near Diversey Parkway in the Lake View neighborhood. An except:
“Not yet were his Loop directions familiar. He was gazing north, but somewhere behind all that muck and masonry, poor little Jo would be threading the snakes of her switchboard and hoping for one o’clock, when she could hurry to a cafeteria, buy her spaghetti and eclairs, and window-shop for twenty minutes. So many other Jos, too, all typing and grinding back of their coarse walls…So many Marrys, he realized with startling surprise, all wondering and longing for vague mists that clung to El platforms and wreathed the areaways above coughing meat trucks or florists’ deliveries.”
The Women (2009) by T. Coraghessan Boyle — The prolific Boyle has written novels and short stories covering, like Pynchon, a dizzying array of genres and subjects. In The Women, he gives a fictional account of Frank Lloyd Wright’s life through the prism of his relationships with four women. An excerpt:
“Was she delusional? He announced at dinner one evening that he was going into Chicago on business in the morning—he’d stay over a few days—and she didn’t think a thing of it, beyond the fact that he was taking a suitcase with him and a raft of his prints to sell…or that Union Station was an infestation of tracks that could have taken him anywhere—west, even, to Colorado.”
So Big (1924) by Edna Ferber—Ferber is best known for her 1926 novel Showboat, adapted as a Broadway musical (with such now-standards as “Ol’ Man River”) and as a movie three times. Although many of her novels took place in settings, such as Texas and Alaska, where she had never lived, Ferber had been a Chicagoan for a time, and So Big tells the story of a young woman living in the suburb of South Holland and, to a lesser extent, in Chicago itself. An excerpt:
“‘So many of her friends [said Dirk] are moving to the north shore, away from these hideous south-side and north-side Chicago houses with their stoops, and their bay windows, and their terrible turrets. Ugh!’
“‘Well, now, do you know,’ Selina remonstrated mildly, ‘I like ‘em. I suppose I’m wrong, but to me they seem sort of natural and solid and unpretentious, like the clothes that old August Hempel wears, so square-cut and baggy. Those houses look dignified to me, and fitting…They have a certain rugged grandeur. They’re Chicago.’”