The Windy City Is a Written-About City

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Chicago’s skyline. (Photo by Kelly Liu/Getty Images.)

Newly named Pope Leo XIV was born Robert Prevost in Chicago, so that’s as good an excuse as any to write a blog post about novels partly or fully set in “The Windy City” off Lake Michigan.

With a population of more than 2.6 million, Chicago is America’s third-largest city after New York City and Los Angeles, so there were and are plenty of stories to be told in a Midwest metropolis known for its diversity, urban architecture, commerce, arts institutions, sports teams, etc., etc.

On a personal note, my wife Laurel Cummins (Happy Mother’s Day!) was born in Chicago. Also, I went to graduate school at Northwestern University, just north of Chicago in Evanston, Illinois. Needless to say, I often took the “El” to Chicago during that year, and have since visited the city several times.

One of the best-known novels with a Chicago setting is Upton Sinclair’s The Jungle, a searing 1906 book depicting the struggles of its working-class characters and the horrendous conditions in the meat-packing industry.

Another Chicago-based classic is Richard Wright’s Native Son (1940) — which, among other things, depicts the city’s very complicated racial dynamics.

Theodore Dreiser’s two best-known novels are mostly or partly set in Chicago; those books being Sister Carrie (1900) and An American Tragedy (1925).

Published during one of the years between those Dreiser books was Willa Cather’s 1915 novel The Song of the Lark, in which future opera singing star Thea Kronborg studies music in Chicago.

Then there’s W. Somerset Maugham’s The Razor’s Edge (1944), in which the traumatized World War I pilot protagonist is from Chicago.

A 21st-century novel — Audrey Niffenegger’s 2003 bestseller The Time Traveler’s Wife — is an ode to Chicago amid its offbeat love story and frequent time-jumping.

The main character in Stephen King’s Rose Madder (1995) escapes an abusive police officer husband by fleeing to an unnamed big city that’s almost certainly Chicago.

Saul Bellow set a number of his novels in Chicago, but the only one of his I’ve read (Seize the Day) unfolded in New York City. 🙂

The title character of John Grisham’s 2012 baseball novel Calico Joe has a brief career with the Chicago Cubs.

I’ll add that while Eliot Asinof’s 1963 baseball book Eight Men Out is basically nonfiction, it does have some fictional elements. And the true story about eight Chicago White Sox players paid to “throw” the 1919 World Series for the benefit of gamblers is almost novelistic in its drama.

Your thoughts about, and examples of, this topic?

Misty the cat says: “Me eating. Birds eating. It’s a Sunday brunch frenzy.”

My comedic 2024 book — the part-factual/part-fictional/not-a-children’s-work Misty the Cat…Unleashed — is described and can be purchased on Amazon in paperback or on Kindle. It’s feline-narrated! (And Misty says Amazon reviews are welcome. 🙂 )

This 90-second promo video for my book features a talking cat: 🙂

I’m also the author of a 2017 literary-trivia book…

…and a 2012 memoir that focuses on cartooning and more.

In addition to this weekly blog, I write the 2003-started/award-winning “Montclairvoyant” topical-humor column every Thursday for Montclair Local. The latest piece — about an aging ice rink, a probably doomed-to-fail affordable housing plan, and more — is here.

98 thoughts on “The Windy City Is a Written-About City”

  1. Like your wife, I, too, was born in Chicago. The last book I read featuring Chicago was The Devil in the White City- absolutely fascinating nonfiction book about the World’s Fair and a serial killer I had never known about. I love to visit Chicago whenever I can…all the museums, and concerts at Ravinia!

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    • Thank you, Lori! Nice to hear that you’re also a Chicago native! It IS a very interesting place to live in or visit. I appreciate you mentioning “The Devil in the White City”; it sounds like a very compelling and harrowing book.

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  3. Rose Madder creeped me out for weeks! I guess at the time, I never considered Chicago as the city. Also, my great-grandmother’s last name was Cummins. I wonder if I’m related to your wife!?! (Her maiden name was Lydia Cummins- Scottish.)

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  5. Sorry I didn’t answer soon, Dave. We just got back from three weeks in Romania. Lots of catching up. The book I immediately thought of–one of my best novels of 2024–was HELLO BEAUTIFUL, which has already been mentioned by Madeline and perhaps others. I think Chicago is a fascinating city with a great art museum, and I’ve been there a couple of times in my life for short visits, but at this point, I can think of any other Chicago-based books I’ve read, except for the also already mentioned mysteries by Sara Paretsky.

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    • Thank you, Kim! Your comment is not late at all. 🙂 I hope you had a very enjoyable trip to Romania! (One of my grandparents immigrated from there.) Three weeks is a very nice stay. I appreciate the two Chicago-related authors/books mentions! Glad you got to visit that city a couple of times, and the museums are indeed first-rate.

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  7. Hi Dave,

    I read this yesterday, but know absolutely nothing about Chicago and so had nothing to add. Except maybe wasn’t John Grisham from there? A quick Google, and no, he was absolutely from the south, which, yes, I already knew that.

    Anyway, skip forward a few hours and I’m watching a quiz show and the question is something like which city did Michael Jordan play in when he played for the Bulls? And just a day earlier I might have guessed somewhere in California, but no, now that’s a random piece of trivia that I’ll probably remember for the rest of my life (though I have trouble remembering my address). So thanks for giving me a bonus point in whatever show I was watching 🙂

    Sue

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    • Thank you, Sue! Quite a coincidence that Michael Jordan of the CHICAGO Bulls came up on that quiz show. 🙂 And it’s impossible to know a lot about every city, especially those thousands of miles away from where one lives. I went online to see what the third-largest city is in Australia (as Chicago is the third largest in the U.S.), and came up with Brisbane. My point? I know very little about Brisbane. 🙂

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      • To add to the little that you know – our tourism slogan a few years ago was beautiful one day, perfect the next. It gets a bit warm and sticky in summer, but our winters are fantastic. Always sunny, not too hot, not too cold. Until this year when it has. not. stopped. raining 😦 I still wouldn’t want to be anywhere else though. I love Brissy ❤

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  8. A great topic, Dave. Chicago’s rich history, diverse neighborhoods, iconic architecture, vibrant arts scene, and complex social dynamics provide a wealth of compelling material for writers, making it an exceptionally interesting city to set a book in.

    As you may know, I love reading Erik Larson’s books. They are non-fiction but he writes in an easy style that can only be considered page-turners. I have read “In the Garden of Beasts” a couple of times and just finished “Dead Wake: The Last Crossing of the Lusitania.” I am now embarking on “The Devil in the White City” which intertwines the stories of the 1893 Chicago World’s Fair and a serial killer, H.H. Holmes, who used the fair to lure victims to his elaborately constructed “Murder Castle.” Daniel Burnham, the architect behind the fair, races against time and immense challenges to create a spectacle of innovation and grandeur, while Holmes preys on unsuspecting visitors amidst the fair’s dazzling attractions. Larson masterfully juxtaposes these parallel narratives, highlighting the brilliance and dark underbelly of a pivotal moment in American history.

    I must leave a quote that speaks to the allure of Chicago!!!

    “Place has always been important to me, and one thing today’s Chicago exudes, as it did in 1893, is a sense of place. I fell in love with the city, the people I encountered, and above all the lake and its moods, which shift so readily from season to season, day to day, even hour to hour.” Erik Larson, The Devil in the White City

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    • Thank you, Rebecca! Erik Larson, who I’ve never read, sounds like a VERY compelling nonfiction author! And I like that excerpt of his you cited at the end of your comment. Lake Michigan does have many moods as it hugs the shore of Chicago and Evanston. I remember many bike rides along the lake from my apartment to the Northwestern campus — watching the waves, the sunlight on the water, etc. And seeing the lake freeze up and “steam” during the winter (I wasn’t cycling on those days 🙂 ).

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  9. A very appropriate moment to feature Chicago, Dave. Sad to say, and not surprisingly, I haven’t read any of the novels you’ve mentioned, but I’ve seen countless movies filmed in “The Windy City.”

    You brought to mind a funny rhyme we recited as kids growing up in Guyana: “Chicken in the car and the car can’t go. / That’s the way to spell Chicago.” 😀

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  10. Many thanks, Dave, for the interesting news I can read here about Chicago, probably thanks to the new pope! I remember having read, a long time ago, a novel about the poor workers in the meat-packing industry, which still gives me goose-pimples, if I think of it and I suppose that it was the one you mentioned or “The Jungle”

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  11. Chicago is quite close to us – just an hour or so away! 🙂 I got tickled to see you mention the Jungle. Not because it’s a book that makes a person laugh (one of those reads that always sticks with ya, to say the least) but because I do have kind of a funny story attached to it. When I was quite young still, I really wanted to read it. Because a lot of my history books kept mentioning it and I just really wanted to experience that story. So at the bookstore, I tricked my mom into buying it for me by telling her it was like the Jungle Book haha! Perhaps I was a bit young for it at the time, but I handled it well and I honestly think about it still even to this day.

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    • Thank you, M.B.! Congratulations on the successful trickery of your mom. 🙂 Some people can handle mature books at a young age, and you were one of them! And nice that you’re within easy occasional visiting distance of Chicago!

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  13. The only one I could think about was the author, Sara Paretsky (and she was mentioned earlier). I have read many of those books – V. I. Warshawski (Vic) the private investigator from Chicago – she’s brilliant (I would say).

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  14. What an interesting post; I’ve never thought about or read novels set in Chicago before. Richard Wright’s Native Son (1940) sounds like an intriguing book. I might give it a go, as I do love stories set in American cities (Midnight Cowboy is one of my all-time favorite reads!). 😊

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    • Thank you, Ada! “Native Son” is a really compelling classic. I haven’t read it since high school, but still remember a lot of it. I didn’t know “Midnight Cowboy” had been a novel before the famous movie! Glad you mentioned it! Now on my to-read list.

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  15. Great idea to highlight Chicago, as New York City is the setting for lots of books, but what about the Windy City? Your mention of “The Jungle” made me remember reading the book in school and being horrified by the conditions where people worked. It was certainly an important book for pointing out those conditions. I couldn’t think of other examples for your topic, so I asked Google for help. And from a list on Goodreads, I saw “Dark Matter” by Blake Crouch. I forgot that was based in Chicago. It’s a neat read about parallel worlds. The book didn’t include this, but maybe there’s a parallel world in which Misty the cat is governor of New Jersey?

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    • Thank you, Dave! Yes, NYC has probably inspired the most literature among U.S. cities, but there’s definitely plenty of fiction set in Chicago (as well as Los Angeles and some other U.S. cities).

      “The Jungle” is indeed a very powerful, disturbing read. And “Dark Matter,” with its parallel worlds, sounds very intriguing!

      Ha! 😂 Misty the cat is mayor of his apartment complex, so governor of New Jersey might be the next logical step. 🙂

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  16. Hi Dave!

    Interestingly, I think ‘Rose Madder’, by Stephen King is his best book!! Being from the UK I did try to work out the location it was set in. I later learnt that he deliberately left the location vague!! Chicago, sounds about right. Thank you Dave, another fascinating post, some lovely books!!

    Have a good week.

    Sharon

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    • Thank you, Sharon! “Rose Madder” is definitely a riveting novel. Very realistic (including a searing/disturbing look at domestic violence), and then it gets kind of fantastical.

      Have a great week, too!

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  17. I didn’t know you had spent time in Chicago. I lived there for four years back in the day. It is a BIG city with plenty of things to do and see, that’s for sure. It was a bit too big for my liking — but that’s just me. I got enough snow to last me for a lifetime during those four years and have not been back since. Interesting run down of all the Chicago related literature. I need to go back and revisit some of these.

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    • Thank you, Sheila! Yes, one year very near Chicago; my apartment in the south part of Evanston was literally two blocks from the city. 🙂 I didn’t know you spent four years in Chicago! Definitely an interesting memory for you. I liked the bigness of Chicago when I was in my 20s, but I also like things a little calmer now. 🙂 And, yes, all that snow — about 80 inches the one winter I was there. Ugh.

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  18. I liked “The Lazarus Project” by Aleksandar Hemon. I believe some of his other books are also set in Chicago though I have not read any of them. I also associate poet Carl Sandburg with Chicago. (K)

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    • Thank you, Kerfe! I appreciate the mention of “The Lazarus Project” and Aleksandar Hemon, and you’re right that one associates Carl Sandburg with Chicago. (And with his biography of Lincoln, among other works.)

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  19. I’m still wrapping my head around a Pope from America, Chicago,IL!

    I will say when I think of Chicago, a city i would like to visit one day,I think of the Kander and Webb musical, the music is infectious I play on my IPOD at gym on a continuum, the Fosse choreography ++ I’d have to try deep dish pizza if I go to Chicago.

    I also think of mobsters like Al Capone ,Murder Inc. I think you’ll agree Dave,a great Springsteen song!

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    • Thank you! It IS hard to believe there’s an American-born pope!

      Yes, the “Chicago” musical. 🙂 And I loved deep-dish pizza when I lived near Chicago.

      I agree that “Murder Incorporated” is one of Springsteen’s better mid-career songs.

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  20. A fitting topic and an interesting city. I would love to visit some day. Chicago was a city that drew a lot of Scandinavian immigrants in the late 1800’s and early 1900’s – my great grandfather emigrated from Sweden to Chicago in 1905. It seems there were many religious congregations there as well – it was in this city my great grandfather became a Christian and this later spurred him to becoma missionary in China. I will surely pick up one of your book suggestions to get more of a feel for the city 🙂

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    • Thank you, Thérèse! Great that you have an interesting family history with Chicago, which — like some other parts of the American Midwest — indeed has quite a few descendants of Scandinavian immigrants. I hope you get to visit Chicago someday!

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  21. Chicago has such a storied history that I think many characters could be drawn from the area in almost any time period. I’m drawing a blank on characters/books at the moment, Dave and to be honest, I don’t recognize all the ones you mentioned. But, I enjoyed the post and I look forward to more of the comments. I do have characters in my books who are from Chicago, but other than having worked for the Tribune, there is nothing that ties them to the city.

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    • Thank you, Dan! Yes, Chicago is so big and significant in the U.S. that some past and present literature would reflect that. Former Chicago Tribune staffers in your books — nice! I knew a number of people who worked for that newspaper and the Chicago Sun-Times from when I worked for a magazine covering the newspaper biz.

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  22. I am sure I will come up with a book tomorrow. But I am smiling because earlier I was speaking to what might just be my oldest friend,… I don’t see her very often, but we were talking about the film Calamity Jane cos she loved that film and in particular we were talking about ‘I Just blew in from he Windy City’ and how we used to act it out. So really this is kinda ‘spooky….’

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  23. I’m afraid you have me beaten on this one, Dave. I’ll have to plead extreme Englishness and a limited knowledge of Chicago, aside from several movies and TV series set there. Should I remember any books I’ve read set in the city I’ll be sure and let you know. Sorry. 😦

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  24. I’m not Catholic, but Leo XIV is likely to be one of the three best known Illinoisans in history after Presidents Lincoln and Obama and he was the only one born in Illinois.

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    • To the best of my knowledge, Ronald Reagan was the only U.S. President born in Illinois, but he was considered a Californian rather than an Illinoisan. Which state a native born American identifies with can be complicated sometimes. On another matter Hemingway was more associated with Paris and Spain than with Chicago.

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      • True, Tony, that a person being a native of one state can be associated more with another state. And, yes, Hemingway’s Oak Park, Illinois, birth feels like merely a footnote in his life. He wanted badly to be in what he considered more interesting places.

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  25. It was as horrifying, but I used to work for the FBI, and there was no way I could see an FBI agent going undercover in the UK with no backup and no plan. Too unbelievable. (Not to mention that the author made it sound as if the FBI relies on ghosts as part of their evidence gathering.)

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  28. I remember reading an article, many years ago, by Studs Terkel re: his observations concerning working people. I think in this article he interviewed a number of characters. It’s been so far back in the past I don’t recall the particulars. I found it interesting primarily because I’ve always liked to watch people work similar to the fascination I have watching artists paint or sculpt. Anyway, he had a significant connection to Chicago and was an amazing interviewer, radio host and novelist. Here’s a link about him: https://apwu.org/news/studs-terkel-voice-work-and-american-worker

    Happy mother’s day to all moms as well, and speaking of mother’s day and work, I’ll leave this little proverb– “A man works from sun to sun, but a mother’s work is never done.”

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    • Thank you! Yes, Studs Terkel was indeed a terrific writer associated with Chicago. Glad you mentioned him! Also in the nonfiction realm, the columnist and author Mike Royko was a compelling Chicago writer with a working-class bent.

      That classic proverb is a little out-of-date, with women in the paid workforce and sone men doing their share of housework and child-rearing, but there’s still plenty of truth to it. 🙂

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      • I think I read that Terkel article in the AFL-CIO news my dad would receive. Dad was a FireFighter (Houston) and was very active in the union. I was reading his news because I became interested about what businesses to boycott, and I wasn’t even old enough to work. Ha. So Terkel was a little before my time. It was the 60s and my literary interests veered off into another direction.

        And yes that proverb is a little dated. I ran across a modernization of it re: “a mother’s work is never done because she doesn’t get paid for it.” Nice theme Dave. Susi

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        • Thank you, Susi, for the follow-up comment! Nice that your dad was a firefighter and a very active union member! (My father was also working class: a radio and TV repairman.)

          So many companies deserve boycotting…

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  29. I’m glad you mentioned Upton Sinclair’s “The Jungle”. He was a prolific writer and earned his reputation of “muckraker” from US President Theodore Roosevelt when that book came out. Public awareness of the filth in the packaged meat industry also gave rise to TR’s “Pure Food and Drug Act”, which led to the creation of the FDA.
    I vaguely remember Maugham’s “The Razor’s Edge”. My mother, now in heaven (I hope), always claimed Maugham was her favorite author. I still have her copies of his books.
    For the record, Hillary Clinton was also born in Chicago.

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    • Thank you, Katharine! You’re absolutely right that “The Jungle” was a VERY influential book — one of a small number of novels that really changed things.

      While Maugham isn’t my favorite author (as he was for your late mom), he was a great writer. In addition to “The Razor’s Edge,” I’m a big fan of his novels “Of Human Bondage,” “The Moon and Sixpence,” “The Painted Veil,” and “Cakes and Ale.”

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  32. Happy Mother’s Day to all mothers!

    So, I did think of 3 books.

    A Raisin in the Sun by Lorraine Hansberry is set in Chicago. Originally a play, It has actually been adapted into a novel.

    I find this interesting, as usually it’s the other way around. Novels are adapted into plays or films.

    I must mention The First Time by Joy Fielding. (a wonderful story)

    One of my faves, The Untouchables, is actually a memoir by Eliot Ness and Oscar Fraley.

    I bet many did not know it was a memoir, even though they know Eliot Ness was a real person.

    Chicago is a cool topic, Dave, windy even.

    I like that … windy. Think I’ll start saying “that’s windy” instead of “that’s cool”.

    Hope I have better luck with that than I’ve had with bringing back “Groovy”!

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    • Thank you, Resa! Great mention of “A Raisin in the Sun,” which I have seen on stage. Didn’t know that there was a novel version of it! And nice that Joy Fielding has used a Chicago setting in addition to Toronto, Florida, etc.!

      “Chicago is a cool topic, Dave, windy even” — ha! 😂 When I finished graduate school near the city, I didn’t job-hunt there because I wanted to flee the cold. The weather that winter was not…groovy. 🙂

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      • Windy! So you escaped to the tropics. 🥵
        Careful of those hot spices. They are pretty windy too!
        Harsh winter! I grew up in Winnipeg, Canada’s windy city. Many -40 days in the winter (or worse). I remember rolling home (like summersaults)in snow storms a couple of times.
        Now… I’d have to roll home like a cabbage roll, on my side. Gotta wonder how that would work out? Might make a groove? 🤔

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        • LOL! 😂 (Some of your comment.)

          Well, New York City (where I ended up) was a little warmer than Chicago. 🙂 And, yes, parts of Canada are quite a bit colder than Chicago — as you know. I did live in Chicago during a particularly harsh winter, with about 80 inches of snow and temperatures below zero (Fahrenheit) for parts of about 30 days. Some of Lake Michigan froze over. 😲

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          • I lived in Winnipeg for 4 years, and I believe it should be called the Windy City (although I live near Detroit now, and we get plenty of wind here, too–I think as much as Chicago but not as much as Winnipeg).

            I recently read Hello Beautiful by Ann Napolitano, which is set in the Pilsen section of Chicago.

            The Devil in the White City by Erik Larson, historical fiction set in Chicago. (I recently started reading Death Behind Every Door which brings the story to the present day and the dark web, but I gave up because the FBI agents were too unrealistic.)

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            • Thank you, Madeline! I guess there are windier cities than Chicago. 🙂 And I appreciate the mentions of Hello Beautiful and The Devil in the White City. Sorry the sequel to the latter wasn’t as good as it could have been.

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