Has there ever been a better year for funny books about Chicago? Thanks to a pithy rap memoir, an absurdist satire of the mayor’s office, and a pair of comedic novels, 2022 offered Chicago readers a refreshing dose of literary laughs. Per usual, I’ve limited this list to books with a strong focus on the city itself, so you won’t see local author Jessamine Chan’s riveting The School for Good Mothers, since it’s set in Philadelphia, nor Jeff Deutsch’s fascinating In Praise of Good Bookstores, since it bounces all over the world. With that in mind, here are my ten favorite Chicago-focused books of 2022, including fiction, nonfiction, and poetry.

Mount Chicago by Adam Levin (Doubleday)

Few books will ever make you laugh out loud as frequently as Adam Levin’s third novel, a metafictional epic about a massive sinkhole that destroys the Loop. Of course, the mayor insists on calling it a “terrestrial anomaly,” since sinkholes “made you think of swamps and they made you think of armpits,” and “people in mourning did not need that.” Alternating between the perspectives of a Jewish novelist whose family died in the tragedy and a 20-something mayoral aide, it’s an absurdist skewering of Chicago politics grounded by emotional realism—and a perfect book for fans of Kurt Vonnegut and George Saunders. (Disclosure: I took several creative writing courses taught by Levin at Roosevelt University more than a decade ago.)

Even Though I Knew the End by C. L. Polk (Tordotcom)

C. L. Polk doesn’t live in Chicago, but their latest noir fantasy novella is set in the city during the 1940s and commands a strong sense of place. It stars a warlock detective named Elena Brandt who literally makes a deal with the devil to save her brother’s life. With only a few days left before her deal expires—and desperate to spend more time with her soulmate, Edith Jarosky—Elena embarks on one last investigation that could save her from Hell: tracking down a gruesome serial killer called the White City Vampire. It’s as fun as it sounds, and if there’s a God, we’ll get a sequel or two.

Chicago in Stone and Clay: A Guide to the Windy City’s Architectural Geology by Raymond Wiggers (Northern Illinois University Press)

“The city is not a denial of nature. It’s a vast affirmation of it,” Wiggers writes in this first-of-its-kind guide to the geology of Chicago’s architecture. In surprisingly breezy chapters organized by neighborhoods and buildings, Wiggers explores the stone, brick, terra-cotta, plaster, metal, and ornamental glass that make Chicago an enormous outdoor museum. It adds a fascinating new layer of history to your brain that will change the way you see the city.

Her Word is Bond: Navigating Hip Hop and Relationships in a Culture of Misogyny by Cristalle “Psalm One” Bowen (Haymarket Books)

Cristalle Bowen—also known by her stage name “Psalm One”—has a “creative stamina and drive matched by few Chicago rappers,” according to Leor Galil, and her debut memoir is further proof. With an unmistakable voice and sense of humor, Bowen narrates her own life story growing up in Englewood, attending Whitney M. Young Magnet High School, keeping her sexuality a secret “for decades,” and battling misogyny as a trailblazing emcee with Nacrobats, Rapperchicks, and Big Silky. It’s funny, heartbreaking, enlightening, and a must-read for local music-heads and scholars of midwest hip-hop.

Marrying the Ketchups by Jennifer Close (Knopf)

Jennifer Close’s new multigenerational novel about an Irish American family running an Oak Park burger joint is both wholesome and hilarious. Set during the surreal mid-2010s when the Cubs won the World Series and Trump won the presidential election, Marrying the Ketchups kicks off with the death of the Sullivan paterfamilias. His children and grandchildren are then pulled back into the orbit of the restaurant as they struggle to define themselves in Chicago, Oak Park, and Lake Forest.

Last Summer on State Street by Toya Wolfe (William Morrow)

Set in the summer of 1999, Toya Wolfe’s debut novel is inspired by her own childhood growing up in the Robert Taylor Homes along State Street, as they were slowly demolished. Last Summer on State Street is a coming-of-age story about a group of 12-year-old girls who “ran around in this tight formation, snapping through the block in neon colors like a school of tropical fish.” It’s a brilliant debut that joins Gwendolyn Brooks’s Maud Martha as one of the best novels ever written about Bronzeville in particular and the south side in general. 

When Franny Stands Up by Eden Robins (Sourcebooks Landmark)

Pitched as a cross between The Marvelous Mrs. Maisel and A League of Their Own, this period piece is about a young Jewish woman named Franny Steinberg who turns her personal trauma during and after World War II into a career as a standup comedian in Chicago. But Eden Robins doesn’t just go for laughs—When Franny Stands Up is also a powerful story about antisemitism and the oppression of women in midcentury America, with fun historical cameos from the Palmer House Hotel, Marshall Field’s holiday window displays, and more.

Super Sad Black Girl by Diamond Sharp (Haymarket Books)

When publishers refer to a book as “a love letter to Chicago,” you know you’re in for something special. Diamond Sharp’s debut poetry collection is a dazzling and devastating heir to the verse of Gwendolyn Brooks and the dialogue of Lorraine Hansberry—two legendary south-side writers who speak to Sharp throughout these poems as she suffers from depression. Sharp’s truly unique perspective of the city belongs on your shelf next to Eve Ewing’s 1919 and Cortney Lamar Charleston’s Doppelgangbanger.

Book of Extraordinary Tragedies by Joe Meno (Akashic Books)

In his latest novel set around the Great Recession, Joe Meno returns just south of city limits to the neighborhood where he grew up: Evergreen Park. Book of Extraordinary Tragedies is about a 20-year-old musician named Wolfgang Amadeus Aleksandar Fa, who is slowly going deaf and is desperate to escape what feels like a century-old curse of poverty and ill-fortune on his Eastern European family. With his nuanced portrayal of Chicago’s ethnic, class, and cultural dividing lines, Meno once again proves himself a true heir to Stuart Dybek for the way he captures the essence of life in our neighborhoods.

The Billboard by Natalie Y. Moore (Haymarket Books)

Natalie Y. Moore’s powerful play about an Englewood abortion clinic turned out to be far more timely than she ever could have imagined; it premiered at the 16th Street Theater this summer during the same week the U.S. Supreme Court overturned Roe v. Wade. This book features the entire script alongside a stunning foreword from Imani Perry, author of Looking for Lorraine: The Radiant and Radical Life of Lorraine Hansberry and an afterword from Jane Saks, the founding executive director of the Institute for the Study of Women and Gender in the Arts and Media at Columbia College Chicago.

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Has there ever been a better year for funny books about Chicago? Thanks to a pithy rap memoir, an absurdist satire of the mayor’s office, and a pair of comedic novels, 2022 offered Chicago readers a refreshing dose of literary laughs. Per usual, I’ve limited this list to books with a strong focus on the city itself, so you won’t see local author Jessamine Chan’s riveting The School for Good Mothers, since it’s set in Philadelphia, nor Jeff Deutsch’s fascinating In Praise of Good Bookstores, since it bounces all over the world. With that in mind, here are my ten favorite Chicago-focused books of 2022, including fiction, nonfiction, and poetry.

Mount Chicago by Adam Levin (Doubleday)

Few books will ever make you laugh out loud as frequently as Adam Levin’s third novel, a metafictional epic about a massive sinkhole that destroys the Loop. Of course, the mayor insists on calling it a “terrestrial anomaly,” since sinkholes “made you think of swamps and they made you think of armpits,” and “people in mourning did not need that.” Alternating between the perspectives of a Jewish novelist whose family died in the tragedy and a 20-something mayoral aide, it’s an absurdist skewering of Chicago politics grounded by emotional realism—and a perfect book for fans of Kurt Vonnegut and George Saunders. (Disclosure: I took several creative writing courses taught by Levin at Roosevelt University more than a decade ago.)

Even Though I Knew the End by C. L. Polk (Tordotcom)

C. L. Polk doesn’t live in Chicago, but their latest noir fantasy novella is set in the city during the 1940s and commands a strong sense of place. It stars a warlock detective named Elena Brandt who literally makes a deal with the devil to save her brother’s life. With only a few days left before her deal expires—and desperate to spend more time with her soulmate, Edith Jarosky—Elena embarks on one last investigation that could save her from Hell: tracking down a gruesome serial killer called the White City Vampire. It’s as fun as it sounds, and if there’s a God, we’ll get a sequel or two.

Chicago in Stone and Clay: A Guide to the Windy City’s Architectural Geology by Raymond Wiggers (Northern Illinois University Press)

“The city is not a denial of nature. It’s a vast affirmation of it,” Wiggers writes in this first-of-its-kind guide to the geology of Chicago’s architecture. In surprisingly breezy chapters organized by neighborhoods and buildings, Wiggers explores the stone, brick, terra-cotta, plaster, metal, and ornamental glass that make Chicago an enormous outdoor museum. It adds a fascinating new layer of history to your brain that will change the way you see the city.

Her Word is Bond: Navigating Hip Hop and Relationships in a Culture of Misogyny by Cristalle “Psalm One” Bowen (Haymarket Books)

Cristalle Bowen—also known by her stage name “Psalm One”—has a “creative stamina and drive matched by few Chicago rappers,” according to Leor Galil, and her debut memoir is further proof. With an unmistakable voice and sense of humor, Bowen narrates her own life story growing up in Englewood, attending Whitney M. Young Magnet High School, keeping her sexuality a secret “for decades,” and battling misogyny as a trailblazing emcee with Nacrobats, Rapperchicks, and Big Silky. It’s funny, heartbreaking, enlightening, and a must-read for local music-heads and scholars of midwest hip-hop.

Marrying the Ketchups by Jennifer Close (Knopf)

Jennifer Close’s new multigenerational novel about an Irish American family running an Oak Park burger joint is both wholesome and hilarious. Set during the surreal mid-2010s when the Cubs won the World Series and Trump won the presidential election, Marrying the Ketchups kicks off with the death of the Sullivan paterfamilias. His children and grandchildren are then pulled back into the orbit of the restaurant as they struggle to define themselves in Chicago, Oak Park, and Lake Forest.

Last Summer on State Street by Toya Wolfe (William Morrow)

Set in the summer of 1999, Toya Wolfe’s debut novel is inspired by her own childhood growing up in the Robert Taylor Homes along State Street, as they were slowly demolished. Last Summer on State Street is a coming-of-age story about a group of 12-year-old girls who “ran around in this tight formation, snapping through the block in neon colors like a school of tropical fish.” It’s a brilliant debut that joins Gwendolyn Brooks’s Maud Martha as one of the best novels ever written about Bronzeville in particular and the south side in general. 

When Franny Stands Up by Eden Robins (Sourcebooks Landmark)

Pitched as a cross between The Marvelous Mrs. Maisel and A League of Their Own, this period piece is about a young Jewish woman named Franny Steinberg who turns her personal trauma during and after World War II into a career as a standup comedian in Chicago. But Eden Robins doesn’t just go for laughs—When Franny Stands Up is also a powerful story about antisemitism and the oppression of women in midcentury America, with fun historical cameos from the Palmer House Hotel, Marshall Field’s holiday window displays, and more.

Super Sad Black Girl by Diamond Sharp (Haymarket Books)

When publishers refer to a book as “a love letter to Chicago,” you know you’re in for something special. Diamond Sharp’s debut poetry collection is a dazzling and devastating heir to the verse of Gwendolyn Brooks and the dialogue of Lorraine Hansberry—two legendary south-side writers who speak to Sharp throughout these poems as she suffers from depression. Sharp’s truly unique perspective of the city belongs on your shelf next to Eve Ewing’s 1919 and Cortney Lamar Charleston’s Doppelgangbanger.

Book of Extraordinary Tragedies by Joe Meno (Akashic Books)

In his latest novel set around the Great Recession, Joe Meno returns just south of city limits to the neighborhood where he grew up: Evergreen Park. Book of Extraordinary Tragedies is about a 20-year-old musician named Wolfgang Amadeus Aleksandar Fa, who is slowly going deaf and is desperate to escape what feels like a century-old curse of poverty and ill-fortune on his Eastern European family. With his nuanced portrayal of Chicago’s ethnic, class, and cultural dividing lines, Meno once again proves himself a true heir to Stuart Dybek for the way he captures the essence of life in our neighborhoods.

The Billboard by Natalie Y. Moore (Haymarket Books)

Natalie Y. Moore’s powerful play about an Englewood abortion clinic turned out to be far more timely than she ever could have imagined; it premiered at the 16th Street Theater this summer during the same week the U.S. Supreme Court overturned Roe v. Wade. This book features the entire script alongside a stunning foreword from Imani Perry, author of Looking for Lorraine: The Radiant and Radical Life of Lorraine Hansberry and an afterword from Jane Saks, the founding executive director of the Institute for the Study of Women and Gender in the Arts and Media at Columbia College Chicago.

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When the Chicago Bears traded for Chase Claypool, most of us let out a collective sigh of relief that the organization finally got some more help for their young quarterback. That sigh of relief lasted about 30 seconds until we found out what they paid for this help.

The Chicago Bears exchanged their own second-round pick (currently projected to be 34th overall) in the 2023 NFL Draft for WR Chase Claypool. They won a bidding war with their biggest rival in doing so but most of us would likely agree that this is objectively an overpay.

While acknowledging that they did overpay for Chase Claypool, it is also fair to point out that this was a rather necessary one. With the WR free agent market as thin as it projects to be, and the Bears’ dire need for another playmaker, they really had no avenues to directly address this need.

Even if Chase Claypool was made available via trade or released at the end of the season, the price would have been inflated given his standing in the current market of available wide receivers.

Additionally, after moving Roquan Smith and Robert Quinn, a feel-good move was needed to lift the spirits of a deflated locker room.

With all that said, it is his trade price that has severely accelerated expectations for his production on a weekly basis. Knowing what wide receivers have been taken in the second round in the past, Claypool has been under immense pressure to immediately deliver.

Yet it is worth pointing out that for every AJ Brown or Deebo Samuel found in the second round, there has been a Tutu Atwell, Dante Pettis, or dare I say, Anthony Miller.

Chase Claypool’s price put pressure on him to produce for the Chicago Bears.

Had the Bears simply flipped the pick they got from Baltimore for Claypool, I don’t think nearly as much attention is paid to how fast he gets acclimated, as most would see this final half of the season as an “extended offseason” for him to learn the playbook and build some chemistry with Justin Fields before the season ends.

However, no one should be adjusting expectations because the Chicago Bears overpaid in the acquisition, in what was already a very shallow wide receiver market.

This is all about 2023 and what the Bears did by acquiring Chase Claypool at the deadline was give their coaching staff extra runway to figure out what role he thrives best in to better optimize their offseason program.

Additionally, his slow start shouldn’t surprise anyone. It took the Bears till week 6 or 7 to truly start clicking as a passing offense and these were players who spent all summer learning this playbook and getting reps with Justin Fields.

Chase Claypool comes in and through his first 5 games has 12 receptions on 22 targets for 111 yards. Darnell Mooney through his first 5 games this season had 10 receptions on 21 targets for 173 yards.

Even though Mooney got to work with Justin Fields last year, trained with him this summer, learned the playbook with him, and got preseason reps with him, he still struggled out of the gate to find chemistry with his quarterback.

It’s obvious that whatever system the Bears are running has a lot of nuances that take time to pick up. It would further explain their rationale behind bringing a WR in now versus potentially waiting for free agency or the draft.

The Chicago Bears needed immediate depth and another meaningful threat in addition to Mooney and they likely knew upon making the move that it wouldn’t yield immediate dividends. As a result, it’s probably premature to overreact to Chase Claypool’s production or lack thereof to this point.

If we reach this point next year and there are zero improvements, this will likely go down as a major mistake for Ryan Poles and co. Luckily for him, Poles has more than enough cap space and future draft capital to overcompensate if this Claypool move doesn’t pan out.

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Reader senior writer Ben Joravsky riffs on the day’s stories with his celebrated humor, insight, and honesty, and interviews politicians, activists, journalists and other political know-it-alls. Presented by the Chicago Reader, the show is available by 4 p.m. Tuesdays through Fridays at chicagoreader.com/joravsky—or wherever you get your podcasts. Don’t miss Oh, What a Week!–the Friday feature in which Ben & producer Dennis (aka, Dr. D.) review the week’s top stories. Also, bonus interviews drop on Saturdays, Sundays, and Mondays. 

Chicago Reader podcasts are recorded on Shure microphones. Learn more at Shure.com.

Chicago Reader senior writer Ben Joravsky discusses the day’s stories with his celebrated humor, insight, and honesty on The Ben Joravsky Show.

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Reader senior writer Ben Joravsky riffs on the day’s stories with his celebrated humor, insight, and honesty, and interviews politicians, activists, journalists and other political know-it-alls. Presented by the Chicago Reader, the show is available by 4 p.m. Tuesdays through Fridays at chicagoreader.com/joravsky—or wherever you get your podcasts. Don’t miss Oh, What a Week!–the Friday feature in which Ben & producer Dennis (aka, Dr. D.) review the week’s top stories. Also, bonus interviews drop on Saturdays, Sundays, and Mondays. 

Chicago Reader podcasts are recorded on Shure microphones. Learn more at Shure.com.

Chicago Reader senior writer Ben Joravsky discusses the day’s stories with his celebrated humor, insight, and honesty on The Ben Joravsky Show.

Read More