Chicago is a literary city—though it doesn’t always get credit for it—and its many independent, locally owned bookstores have long been the backbone of a thriving bookish culture. Across the city, readers prioritize supporting Chicago shops, Black-owned businesses and indie bookstores that offer not just books, but spaces for representation, discovery and community. And during the holidays, there are few better places to put your money.
If you’re squeezing in some last-minute gift shopping while hoping to support small businesses, Chicago’s bookstores are an easy—and thoughtful—solution. Read on for holiday gift guides and the best books of the year, curated by some of the city’s finest booksellers.
RECOMMENDED: The best bookstores in Chicago
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Pilsen Community Books
Chicago's first employee-owned and operated independent bookstore as of 2020, Pilsen Community Books welcomes readers with wall-to-wall shelves of books spanning every genre. This year, the staff—understandably reflecting on a year marred by loss—has opted against a traditional holiday gift guide. Instead, they gathered favorite titles across thoughtful categories, including books that inspired hope, works by Chicago-based community organizers and selections spanning different eras and civic movements. Shop PCB's holiday gift catalog online here.
Top picks: Perfect Victims: And the Politics of Appeal by Mohammed el-Kurd; Is a River Alive? By Robert Macfarlane; Heaven Looks Like Us: Palestinian Poetry
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Women & Children First
Chicago’s legendary feminist bookstore has been serving Andersonville and beyond since 1979. While its feminist and queer literature selection remains a standout, Women & Children First offers expertly curated picks across all genres, along with fun bundles and subscriptions. Highlights of the store’s holiday guide include the “trust me, bro” section—books that require a leap of faith with major payoff—and a roundup of “books for your cool Gen X mom.” Titles are available both in-store and online. Since August, the shop has encouraged customers to mask seven days a week, making it a strong option for those prioritizing Covid safety while holiday shopping. Shop WCF's holiday gift guide online here.
Top picks: Stag Dance by Torrey Peters; Deep Cuts by Holly Brickley; Will There Ever Be Another You by Patricia Lockwood
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Unabridged Bookstore
At Unabridged, handwritten recommendations from staff line the shelves, offering helpful, heartfelt tips for customers. The store has expanded on that tradition with an extensive list of staff favorites from 2025. From the delightful off-kilter Sky Daddy—about a woman who becomes romantically involved with airplanes—to Ocean Vuong’s widely acclaimed The Emperor of Gladness, the list offers something for nearly every literary predilection. Shop Unabridged's holiday selections online here.
Top picks: Sky Daddy: A Novel by Kate Folk; Wild Dark Shore by Charlotte McConaghy; I Do Know Some Things by Richard Siken
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Call & Response Books
Hyde Park’s Call & Response is a Black women-owned bookstore dedicated to platforming works by writers of color. For readers craving representation and intentionally curated shelves, owner Courtney Bledsoe’s vision doesn’t disappoint. The staff’s holiday gift guide organizes recommendations by reader archetype—“The Curious Young Reader,” “In Their Healing Era” and so on—making it easy to shop for even the trickiest reader on your list. Shop Call & Response's 2025 gift edit online here.
Top picks: Birds of the Great Lakes by Dexter Patterson; The African Gaze: Photography, Cinema and Power by Amy Sall; Children of Chicago by Cynthia Pelayo
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City Lit
Under the stewardship of local resident and former librarian Stephanie Kitchen, City Lit has grown into one of the city’s most formidable—and cozy—bookstores, complete with a fireplace and reading nook. Browse the store’s holiday gift guide for picks by Chicago authors as well as fiction, fantasy and sci-fi and more, then reward yourself with a snack at neighboring Lula Cafe. Shop City Lit's holiday gift guide online here.
Top picks: Shadow Ticket by Thomas Pynchon; Bury Our Bones in the Midnight Soil by V.E. Schwab; Bread of Angels by Patti Smith