Ask a Book Question: The 63rd in a Series (Chicago Stories)

June 25, 2008 | 8 books mentioned 12 3 min read

Rob writes in with this question:

I’m a seventeen year old who is going to be spending five weeks this summer in Chicago (to be specific – Evanston, since I’ll be part of Northwestern’s summer high school music institute). I’m a life-long New Jerseyan, and have never been in the city of broad shoulders for longer than three days.

So, since I like reading books about the place I’m visiting, I was wondering if you could recommend anything that captured the essence of Chicago – I’m looking for works that encapsulate Chicago in the same way Kavalier & Clay encapsulates New York.

I was thinking about The Lazarus Project and Carl Sandburg’s work. Do you have any other ideas?

coverChicago has inspired some of America’s greatest fiction and continues to be a fruitful setting for contemporary writers. I’ve just completed The Lazarus Project (review hopefully forthcoming), and its twinned stories – set in Chicago 1908 and present day Eastern Europe – mine Chicago’s multicultural past and ignominious history. The book, based on the true story of the mysterious death of immigrant Lazarus Averbuch reminded me a lot of The Devil in the White City, Erik Larson’s non-fiction account of the 1893 Chicago World’s Fair and the serial killer who lurked in its shadows (my review here). Both Devil and Lazarus vividly evoke the chaos of Chicago, a turn of the century boomtown of slaughterhouses, nascent industry, and the first “skyscrapers” that was quickly aligning itself as the country’s center after only decades earlier being its frontier.

An interest in this era in Chicago will inevitably lead one to Upton Sinclair, whose 1906 novel The Jungle is a muckraking, contemporary account of the slaughterhouse workers who drove Chicago’s economic engine. The novel is a landmark among American social novels.

coverJumping forward in time, Chicago produced one of America’s greatest novelists, Saul Bellow, who haunted the hauls of Northwestern in the 1930s. Garth writes that “the greatest Chicago novel ever is The Adventures of Augie March, which is highly recommended for someone who liked Kavalier & Clay.” This contention is hard to dispute.

covercoverPatrick points us to another, more contemporary literary lodestar for Chicago: “The poet laureate of Chicago is Stuart Dybek (I mean, I don’t think he actually is, I just think he should be). The Coast of Chicago and I Sailed With Magellan are both absolute must reads. They both entirely take place in Chicago (mostly the South Side, but not exclusively). He’s one of my favorite authors, and somebody who should have a much larger audience.”

Patrick also throws a more recent selection into the mix: “Also, it’s not like a totally Chicago Chicago book, but I think [Joshua Ferris’s] Then We Came to the End is about Chicago in a really interesting way, as it encapsulates life in the Loop, full of business people commuting from all the suburbs, folks who live in Lincoln Park, people who drive up from the South Side. Plus it’s really fun.”

To these I would also add Adam Langer’s well received duo of books set in West Rogers Park, a neighborhood at the northern edge of the city not far from where I used to live: Crossing California and The Washington Story. Finally, anyone interested in Chicago fiction should consider Chris Ware’s landmark graphic novel, Jimmy Corrigan: The Smartest Kid on Earth. It’s another twinned story, with threads taking place in the near present and during 1893 Chicago World’s Fair, for so many the moment of Chicago’s emergence. Ware’s pathos is haunting and his spare, eccentric drawings are mesmerizing. Along with Devil in the White City, it is a favorite of contemporary Chicagoans.

We’ve undoubtedly skipped over much worthy Chicago literature, so please enlighten us with further suggestions in the comments. Rob, thanks for a great question!

created The Millions and is its publisher. He and his family live in New Jersey.


  1. If you're up for something a bit odd, I'd heartily recommend Mark Smith's The Death of the Detective. It's the detective novel as creeping nightmare, with Chicago playing the role of a disturbingly familiar hell. The detective of the title slowly disintegrates as he wanders all over Chicago, seeming to hit every conceivable neighborhood, each of which is carefully and memorably rendered. It's a chilling, unforgettable book.

    Oh, and if I may be allowed to recommend a couple of books from my employer, the University of Chicago Press, how about Ben Hecht'sA Thousand and One Afternoons in Chicago and Mike Royko's One More Time and For the Love of Mike, all collections of great columns from giants in the history of Chicago newspapers. And Royko's book about the first mayor Daley and his machine, Boss, which I only wish my employer published.

  2. I would recommend my own company's Looped, by Andrew Winston, which unlike most Chicago novels does not focus on a particular neighborhood, but rather takes on a much greater breadth of the city through its large, diverse, Altman-esque cast of characters.

  3. The Lazarus Project was a great book, but Chicago was mostly a footnote there to Eastern Europe. But ditto on the Upton Sinclair and Stuart Dybek titles you mentioned – all three are must-reads, along with absolutely anything by Mike Royko (including Boss, his Daley bio). I'd also strongly recommend Nelson Algren's novel The Man With the Golden Arm and story collection The Neon Wilderness (and though his nonfiction Chicago: City on the Make is one of my alltime favorites, its obscure references make it better for a more seasoned Chicagoan than a neophyte), Richard Wright's Native Son, Ward Just's An Unfinished Season and Joe Meno's Hairstyles of the Damned. And those are just for starters.

  4. Thanks everyone, these are awesome. I'll definitely be making multiple trips to the Northwestern bookstore. :-)

    I'd also love to hear anymore suggestions people have, so I'll keep watching the comments.

  5. Richard Wright's Native Son should be on this list. Set in Chicago in the 1930's it chronicles the decline and fall of a young black man named Bigger Thomas–not light summer reading (race, class, the absence of social justice, an unlikeable hero)–but one of the great American novels, I think.

  6. Try Maud Martha by Gwendolyn Brooks. It's a novella set in Chicago's African American neighborhoods during the 1940's, and tells the story of the title character in 34 vignettes. It is Brooks' only work of adult fiction–she was primarily a poet–but she should have written more because I think this book is tremendous. Maud Martha's story is nothing special–no high drama or headline material–the real attraction to this story is in the language Brooks uses to sketch out the arc of a human life, and in the character that Brooks has created in Maud Martha.

  7. Scott Simon of NPR Weekend Edition just published a novel about Chicago, Windy City. I haven't read it yet, but it's in the stack. It's a murder mystery (the mayor is killed), but it's mostly about Chicago politics, from what I've read. If you like detective stories, I would also recommend the early Sara Paretsky detective books featuring V.I Warshawsky. The later books don't have as much Chicago color (I don't know about the most recent books in the series–I stopped reading them about three novels ago). But I lived in Chicago when the earlier books came out, and my friends and I tried to find the bar where V.I. hung out. The descriptions were based on real neighborhoods, but given fictional names.

  8. Sorry I didn't see this topic sooner as I believe that James T. Farrel definitely rates a mention.

  9. One of the few mystery writers I read is Sara Paretsky whose feisty and very socially aware and active PI is based in Chicago. This is where I have learned about the actual people and neighborhoods of Chicago.

  10. Michael Harvey has written two great detective novels that take place in Chicago: The Chicago Way and The Fifth Floor.

    Sean Cherchover's Big City, Bad Blood is also worth a read.

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