Small Business Saturday Preview: 12 Iconic Chicago Shops Worth Supporting This Year

In an era of one-click ordering and same-day delivery, Chicago’s independent retailers face an uphill battle every holiday season. Yet across the city’s neighborhoods, locally owned shops continue to thrive—not by competing with Amazon on convenience, but by offering something the algorithms can’t replicate: personal connection, curated expertise, and roots in the communities they serve.

As Small Business Saturday approaches on November 29, we’ve identified 12 Chicago shops that deserve a spot on your holiday shopping itinerary. These aren’t just stores; they’re neighborhood institutions that have weathered economic downturns, pandemic shutdowns, and shifting consumer habits to remain vital parts of their communities.

Andersonville

Women & Children First 5233 N. Clark St.

For 45 years, this feminist bookstore has been a gathering place for readers, writers, and activists. Founded in 1979, Women & Children First is one of the largest feminist bookstores remaining in North America, offering a carefully curated selection of titles by and about women, LGBTQ+ authors, and marginalized voices. The store hosts more than 100 author events annually and has become a launching pad for emerging writers.

“Every book on our shelves was chosen with intention,” said co-owner Sarah Hollenbeck. “That’s something an algorithm can never replace.”

Woolly Mammoth Antiques & Oddities 1513 W. Foster Ave.

This wonderland of curiosities has been delighting visitors since 2011 with its collection of taxidermy, Victorian medical instruments, vintage scientific equipment, and artifacts that defy easy categorization. Owner Robert Tomlinson sources items from estate sales, auctions, and private collectors, creating a shopping experience that feels more like exploring a cabinet of wonders than browsing merchandise.

Wicker Park

Myopic Books 1564 N. Milwaukee Ave.

Open since 1990, Myopic is a three-story labyrinth of used and rare books where getting lost is half the fun. The store’s cramped aisles and towering stacks reward patient browsers with unexpected discoveries, from first editions to obscure academic texts to vintage pulp paperbacks. It’s the kind of place where you come looking for one book and leave with six.

Una Mae’s 1528 N. Milwaukee Ave.

Vintage clothing enthusiasts have flocked to Una Mae’s since 1995 for its impeccably curated selection of mid-century fashion, from 1950s cocktail dresses to 1970s leather jackets. Owner Stephanie Izard (no relation to the celebrity chef) has an eye for quality and authenticity that has made the store a destination for fashion stylists, costume designers, and anyone seeking pieces with history.

Hyde Park

57th Street Books 1301 E. 57th St.

A fixture of Hyde Park’s intellectual community since 1983, this independent bookstore occupies the basement of a building that once housed a Walgreens. The subterranean setting creates an intimate atmosphere perfect for browsing the store’s strong selections in literature, history, philosophy, and children’s books. The staff’s handwritten recommendation cards throughout the store offer guidance that feels genuinely personal.

Powell’s Books Chicago 1501 E. 57th St.

Not to be confused with its Portland namesake, Chicago’s Powell’s has been buying, selling, and trading used books since 1971. The sprawling store specializes in academic and scholarly titles, making it a treasure trove for University of Chicago students and faculty. Their dollar carts outside the entrance have launched many a lifelong reading obsession.

Pilsen

Pilsen Community Books 1102 W. 18th St.

This volunteer-run bookstore operates on a radical premise: all books are priced at just $1 to $3, with proceeds supporting literacy programs in the neighborhood. Founded in 2017, the store has become a beloved community resource, offering affordable reading material to a neighborhood where rising rents have pushed out many longtime residents.

Knee Deep Vintage 1425 W. 18th St.

Specializing in workwear, Americana, and vintage denim, Knee Deep has carved out a niche serving collectors who appreciate the craftsmanship of mid-century American manufacturing. Owner Marcus Williamson can discourse for hours on the evolution of Levi’s selvedge denim or the relative merits of different era Lee jackets. Prices reflect the quality, but dedicated vintage enthusiasts consider it a pilgrimage site.

Logan Square

Wolfbait & B-Girls 3131 W. Logan Blvd.

This gift shop and gallery showcases work by local artists, with an emphasis on Chicago-themed merchandise that goes far beyond the typical tourist tchotchkes. From letterpress prints of neighborhood maps to hand-poured candles inspired by specific CTA lines, everything in the store celebrates the city with genuine affection and creativity.

Bucket O’ Blood Books and Records 2307 N. Milwaukee Ave.

Horror fans have found a spiritual home at this specialty shop, which stocks an extensive selection of horror literature, exploitation cinema, and vinyl records spanning punk, metal, and everything dark and loud. The store’s name—borrowed from a Roger Corman film—sets the tone for a shopping experience that embraces the macabre with cheerful enthusiasm.

Bucktown

The Boring Store 1331 N. Milwaukee Ave.

Don’t be fooled by the name: this “secret” spy supply shop is actually a front for 826CHI, a nonprofit tutoring and writing center founded by author Dave Eggers. While the spy gadgets and surveillance equipment on display are entertaining, the real mission is supporting creative writing programs for Chicago students. Every purchase funds youth literacy initiatives.

G Boutique 2131 N. Damen Ave.

For 15 years, this women-owned boutique has offered a thoughtfully curated selection of intimates, lingerie, and wellness products in an environment that emphasizes education and empowerment. Owner Tina Gaudette and her staff are known for their knowledgeable, pressure-free approach, helping customers find products that fit their bodies and lifestyles.

Why It Matters

According to the American Independent Business Alliance, for every $100 spent at a local business, roughly $48 stays in the local economy, compared to just $14 when that same $100 is spent at a national chain. Small Business Saturday, launched by American Express in 2010, has become a vital counterweight to Black Friday’s focus on big-box retailers.

“Independent retailers are the heart of Chicago’s neighborhoods,” said Rob Karr, president and CEO of the Illinois Retail Merchants Association. “When you shop small, you’re not just buying a product—you’re investing in your community.”

Many of the stores highlighted above will offer special promotions on Small Business Saturday. Check their social media accounts and websites for details as the date approaches.