Two Recent Novels Set in Chicago

"All roads--always, always--lead back to Chicago."

-Peter Orner, The Gossip Columnist's Daughter

 

More even than Rome? And I thought I was a Chicago booster...

 

I read two new releases set in Chicago. The first one was:

 

Rob Osler/The Case of the Murdered Muckraker (2026)

 

This is the second case in a new series about Harriet Morrow, the Lesbian, bike-riding first female detective at the Prescott Agency in Chicago. It takes place in 1898. The Pinkertons (historical fact) had hired their first female agent not long before, and Theodore Prescott thinks it could work for him as well. But Morrow is still on probation, even in this her second case.

 

Eugene Eldridge is an investigative journalist, who has evidence about corruption among Chicago aldermen. (Shocking, I know.) He's stabbed while in a tenement near the Stockyards. Where did the evidence go? Somebody in the tenement must have seen something, and maybe Morrow, posing as a worker from a settlement house, is more likely to earn their trust?

 

The recurring characters in this series are fun: the orphaned Harriet Morrow, looking after her younger brother, her boss Theodore Prescott, her fellow detectives. Her possible girlfriend. The plot is strong as well. It's a series I'll continue to follow.

 

Peter Orner/The Gossip Columnist's Daughter (2025) 

 

The gossip columnist is Irv Kupcinet, known around Chicago as Kup. He was an actual newspaperman and from 1943 until he died in 2003, he wrote a gossip column for the Chicago Sun-Times. "Among the guests at Joan Crawford's Mental Health Ball at the Conrad Hilton Friday was crooner Vic Damone and Blackhawk Bobby Orr." That sort of thing.

 

In 1963, a few days after JFK was shot, his daughter Karyn "Cookie" Kupcinet died in Los Angeles. Cookie was an aspiring actress with a few credits--her last was a Perry Mason episode--but also with a drug problem. Was it murder, accident, suicide? Was it somehow tied in to the Kennedy assassination? (Almost certainly not, though conspiracy addicts were sure it was.) The case is open even now. Her hyoid bone was cracked, suggesting strangulation, but there's evidence the autopsy was botched. That's all historical fact and it's a good setup.

 

The book is billed as a novel, and Orner tells the story obliquely. Babs and Lou Rosenthal are friends of the Kupcinets--Babs and Essee Kupcinet had both aspired to be dancers and took classes together--and it's their grandson Jedediah Rosenthal, a not terribly successful author and single parent living in Chicago, who is telling the story. It offers a plausible (but not provable) solution to the death of Karyn Kupcinet about halfway through the novel, but that not Orner's real target. In the aftermath of the tragedy, the friendship between the Kupcinets and the Rosenthals falls apart. Why? 

"A friendship ended. In November of 1963, seven years before I was born, a friendship between two couples severed."

Rosenthal's sister jokes in the book to Rosenthal, so how's your auto-fiction going, and I believe, while it says 'Novel' on that matchbook on the cover, it owes a fair amount to Orner's family history. He wrote an earlier novel Love and Shame and Love that covers the same three generations of a Jewish Chicago-area family, with a different last name, but the same family structure.

 

Chicago's my home town, and I sometimes read novels just because they're set there. Chicago's a fairly easy city for such a project, though not as easy as London or Paris, of course. I get curious how they do it. Osler and Orner have fairly different styles. Both men have lived in Chicago but don't currently. Orner grew up in the Chicago suburbs; I'm not sure about Osler.

 

Osler uses fairly well-known landmarks in the city. Theodore Prescott lives on Prairie Avenue and either in visiting him or Prescott's neighbor, Harriet Monroe goes there often. As you can see Prairie Avenue has a Wikipedia article and was once known as Millionaire's Row. People with brand-name names like Pullman, Field, or Armour once lived there, and a couple of years ago I visited one of the mansions myself, now a museum, though when I was a kid the street was considered a no-go zone, and if you drove down it you didn't get out of your car: you were likely to see impoverished Black men warming themselves at fires in barrels. He similarly uses downtown office buildings or the University of Chicago Settlement House.

 

Orner has a different, but curious strategy for locations that works in Chicago, though maybe not elsewhere. He gives an actual address. For example: 1739 W. Jarvis or 711 W. Pratt, Apt. 5D. Often the locations don't actually exist--711 W. Pratt would be in the lake, though not by much--and I can picture the places he specifies. I know exactly the sort of building that would be near the lake at the end of Pratt, and I would be pretty knowledgeable about the socio-economic class of a person living there. (Well-made brick apartment buildings of three stories, a little worn, in better shape now than they were forty years ago. Some of them will have been turned into condos. You could live there cheaply in the 80s. Living there now would cost more.) You can use Google streetview to get a sense of the neighborhood if you don't just happen to know it. But how would it feel if you weren't from Chicago? I'm less certain.

 

Anyway, there could be more said, but this post is long enough, and it's been sitting in my draft folder for a while. Do you particularly enjoy novels set in your hometown or where you live? Double-check them for accuracy? 😉