Holiday Gift Guide for the Chicagoans in Your life

By Allison Yates

Books are some of the best gifts to give. If you’re looking to gift some great reads to the Chicagoans—or friends and family you’re trying to convince to move to the Windy City—here just a few of Read & Run Chicago’s favorite books about the city. There are countless stories that help us better understand the city we call home and each other. Our list is ever growing and this is just the start. If you don’t see your favorite book listed, we likely have it in the works.

But whether your loved ones are nature enthusiasts, history buffs, or foodies, we've got you covered with the list below.

Here’s our holiday gift guide for the Chicagoans in your life.

PS—Did you know? Books are even better when purchased at a locally-owned, independent bookshop (and we’ve got tons!), or online through our bookstore partner that directly supports Queer authors, ShopQueer.co.

For the nature lovers

The Midwest isn’t often considered an outdoor lovers paradise, but at least according to Read & Run Chicago founder Allison Yates it should be. No matter the season, Chicago’s nature is a perfect place for a trail run, hike, or close encounter with flora and fauna of the region. The late Jerry Sullivan’s Hunting For Frogs: And Other Tales from Field & Street is a delightfully fun way to see and experience the Forest Preserves through the eyes of Sullivan’s experience as a nature journalist. For easily-accessible trails in and around the Chicagoland area, Lindsay Welbers’s Chicago Transit Hikes is our bible—and the inspiration for our trail run series.

Get 10% off your copy of The Chicago River: A Natural and Unnatural History by Libby Hill, the comprehensive guide to the history and infrastructure of the Chicago River that inspired our six-part series with guide Chelsey Grassfield, when you shop at Barbara’s Bookstore Loop location. Just mention Read & Run Chicago at checkout.

For the Queer History Buffs

Queer Legacies by John D’Emilio was one of our first events. This digestible and informative book explores some of the lesser-known queer history of Chicago and Illinois through select archives at Gerber/Hart Library and Archives, the largest LGBTQ archives and library in the Midwest, while Rebecca Makkai’s The Great Believers is thoughtful and heavily researched fictional tale inspired by the real-life experiences of Chicagoans during the 1980s AIDS crisis.

For LGBTQ Fiction Fans

Whether you want a close-to-home personal tale of growth set at Halsted and Roscoe or Andersonville-based horror plot, local author David Jay Collins has you covered with Gaybash and Summerdale and Summerdale II. After you Gaybash, bring the book to life with our self-guided route.

The late Valerie Taylor was a writer and activist, and helped portray positive examples of queer women in the pulp fiction genre at a time when queerness was heavily policed, mocked, and primarily used for cis heterosexual men’s voyeurism. The Girls in 3-B is a fascinating example of women’s lives in 1950s Chicago.

For the Activists & Disrupters

Conspiracy to Riot by Lee Weiner showcases on of Chicago’s dark and violent political moments during the 1968 Democratic Convention.

For the Neighborhood Enthusiasts

See new neighborhoods, try new foods, and learn new history with essays from The Chicago Neighborhood Guidebook edited by Martha Bayne and Jessica Mlinaric’s Chicago Scavenger, a riddle-based way to explore Chicago history and culture.

Self-guided routes are available for nine of the Guidebook essays.

For the Foodies

No better way to share the Chicago love than introducing folks to some of our favorite eats—pizza and historic bakeries.

Steve Dolinksy’s The Ultimate Chicago Pizza Guide will leave you sharing pizza fun facts with everyone you know, and Jennifer Billock’s Historic Chicago Bakeries will leave you nostalgic—and with a sweet tooth.

For the People Who Want to Win Chicago Trivia in 2024

Learn about the Great Migration through Isabel Wilkerson’s stunning reporting in The Warmth of Other Suns or through the eyes of young girls in Marcia Chatelain’s South Side Girls, also available in self-guided route format.

Chicago’s Fabulous Fountains by Greg Borzo, Sin in the Second City by Abbott Kahler, and Graceland Cemetery by Adam Selzer all give windows into the making of our city’s infrastructure and culture and spill some juicy details about our political history—and where the term “get laid” comes from.

For the Theater Geeks

Theater lovers will swoon over the frequent settings of Layne Fargo’s Temper, a feminist thriller based on real-life abuse that occurred in a Chicago theater. Run the self-guided route when you finish the tale—a 4-mile jaunt around Andersonville and Lakeview that even includes an unconventional method twist—the CTA!

For the Readers Who Love a Strong Female-Identifying Protagonist

If you’re inspired by strong woman-identifying characters and stories about the various cultural groups that call Chicago home, look no further than the powerful voices in Sahar Mustafaa’s The Beauty of Your Face, Michael Zapata’s The Lost Book of Adana Moreau, Erika L. Sanchez’s I Am Not Your Perfect Mexican Daughter, and Naomi Hirahara’s Clark and Division.

Watch our virtual Q&A with Naomi here.

For Readers Who Love the Memoir

Dawn Turner’s fascinating story of growing up in Bronzeville with her sister and best friend in Three Girls From Bronzeville will leave you hopeful, reflective, and likely in tears.

For Readers Fascinated by Urban Planning & Social Policy

Whether you’re curious about the Loop’s real estate markets, how Lincoln Park became one of Chicago’s most affluent neighborhoods, or what happened when so many Chicago Public Schools closed in 2013, try Rachel Weber’s From Boom to Bubble, Daniel Kay Hertz’s The Battle of Lincoln Park, and Eve Ewing’s Ghosts in the Schoolyard.

Trace the history of Lincoln Park’s development on this self-guided route of Hertz’s book.

For Runners Who Want to Read More About…Running

Sometimes, you just want to read about what we love most: running. Deena Kastor’s memoir Let Your Mind Run will teach you mental toughness skills and inspire your next big endurance event—Maybe the Bank of America Chicago Marathon? Whether in English or Spanish, Pilsen-based trainer and ultramarathoner Edna Jackeline Vazquez Nunez’s Las carreras de mi vida takes us all over the world as Edna becomes the first Mexican-American woman to tackle the 4 Deserts Ultramarathon Series. The races may have been been in some of the most inhospitable conditions in the world, but Edna argues that Chicago winters are excellent training. We couldn’t agree more!

For the Fans of Family Drama

Messy, complicated, loving—if this sounds like any relationships in your life, you’ll enjoy Claire Lombardo’s novel The Most Fun We Ever Had set in nearby Oak Park, IL. After, watch our Q&A with Claire here.

Ready to read more books in 2024? Sign up for our newsletter to get book recs, event info, and more straight to your inbox.

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2023: Our Year in Books

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Trail Runs Inspired by Chicago Transit Hikes