Support Small Business at These Chicago Shops This Holiday Season

Support your community with these local deals.

The holidays are a time for giving thanks, for seasoning everything you consume with pumpkin spice, and for stampeding into Target for a Nintendo Switch. It’s truly the most magical time of the year. Amidst the grateful gluttony of Thanksgiving and the absolute mayhem that is Black Friday, Small Business Saturday is a more modest occasion to encourage patrons to spend their dollars at independent neighborhood businesses—ya know, rather than crowd surf your way through a big box department store.

In Chicago, small businesses are a pivotal part of the city’s vibrant neighborhood patchwork. They may not command the big, ritzy real estate of a downtown conglomerate, but what they lack on Magnificent Mile frontage, they more than make up for in character, charm, and unique maker-made products you won’t be able to find in the tourist-trod byways downtown. From Bronzeville to Rogers Park, these are the types of heartfelt—and often family-owned—businesses that deserve emphasis year-round, but if ever there’s an excuse to patronize an indie artisan or timeworn company, Small Business Saturday is it. Here are 10 great places to shop this holiday season in Chicago.

“If you can shop big box, you can shop essential.” That’s the tagline of the Absolutely Anything Essential Gift Shop, a Black-owned store and venue in Bronzeville stacked with local artisans slinging everything from body scrubs and beard care to mugs, candles, and keepsakes. Like the store name suggests, if there’s a knickknack, accessory, or trinket you may need, whether for yourself or as a gift, the Absolutely Anything Essential Gift Shop likely has it. On Small Business Saturday, the store is hosting a free-to-attend shopping event from 10 am - 5 pm, complete with free arts and crafts opportunities, and special on-site vendors like RP Couture Boutique, Remree’s Blings & Things, and Passion by Design.


Lincoln Square
In spite of his tendency to overstuff his sleigh with bloodthirsty capitalism, Santa has a soft spot for small businesses. Which is why the big man is carving out time from his busy schedule to swing by the Small Business Saturday event in Lincoln Square, where numerous shops are offering special discounts and deals for the occasion. After visiting Santa in the morning at The Perfect Cup, stop off at Neighborly, a decade-old indie institution known for its charming housewares, art, and gifts. For the holidays, the shop features a festive lineup of items like tinsel trees, reindeer piñatas, ornaments, stockings, and artsy renderings of the North Pole. On Small Business Saturday (and Sunday), all items that are Chicago-made are 15% off. After your spree, listen to Dickensian characters sing carols in Giddings Plaza.

Ukrainian Village
Whether you’re looking for copal incense, chunky jewelry, pithy cards, esoteric cookbooks, quirky shin-high socks, air plants, or baby onesies emblazoned with “The Future is Female,” Komoda has it all. Outfitted with enough artsy oddities to inspire a Portlandia skit, the female-owned corner shop is an adorable, cozy nook for all your gift-giving needs—with numerous impulse opportunities for personal purchases, in case you just can’t say no to a masochistic puzzle. A long-standing fixture in Ukrainian Village, Komoda exemplifies the essence of a neighborhood small business; the kind of friendly, warm space where you feel authentically good about spending your money.

Rogers Park
With frigid weather in the offing and inevitable polar vortexes to preempt, ‘tis the season for stockpiling gifts that could provide cozy entertainment long into the winter months. And by “cozy entertainment,” we mean board games so competitive that they may have long-term ramifications in your relationships. The perfect spot to shop for all your gaming needs is Athena Board Game Cafe, a kitschy nook in Rogers Park that doubles as a place to sip lattes and play games on-site, or purchase games to take home. For Small Business Saturday, the shop is participating in a neighborhood-wide incentive that includes specials and discounts at all manner of stores. Kicking off the holiday shopping season, the nearby Welcome Station is offering free coffee, hot chocolate, and tote bags, along with live Christmas music and a holiday-themed 3D snow globe, from 10 am - 2 pm.

Unabridged Bookstore
Unabridged Bookstore

Few industries have been hammered by online retailers quite like independent bookstores, which is why small businesses like Unabridged Bookstore need your support and loyalty now more than ever. The Lakeview institution is a literary wonderland all year long, but in honor of Small Business Saturday, the shop is also offering 10% off purchases both in-store and online, starting at 9 am. For those who shop in-person, Unabridged will also be serving snacks and pastries from next door patisserie, Sugar Daddy, and selling adorable Totes for Tots kids’ tote bags designed by local LGBTQIA+ artist, David Lee Csicsko.

Humboldt Park
From sugar cookies to gingerbread, the holidays are prime time for pastries, and Chicago certainly isn’t lacking in bakeries and stores offering frosted goodies. Sure, you could buy panettone at Eataly, but wouldn’t you feel better about supporting a true-blue mom-and-pop that’s been honing familial recipes for more than a century? For all your holiday dinner party dessert needs, Roeser’s Bakery has your back—just like it always has since opening in 1911. The oldest family-run bakery in the city, this refreshingly frills-free bakery is beloved for its classic American confections, from sugar cookies and coffee cakes to pies, caramel-kissed cupcakes, and custard-y doughnuts. For the holiday season, the homey cafe is filled with gingerbread cookies, yule logs, and frosted Santa cupcakes.

The holidays can be a stressful, hectic, and busy time of year. Fortunately, weed is now legal here. Of the many dispensaries scattered throughout Chicago, one apt option is THC by Chitiva, a Presenting Sponsor in the third-annual Wicker Park Bucktown Chamber of Commerce’s Small Business Saturday 5K. Designed as a unique way to encourage indie shopping (and perhaps working off some of that stuffing), the neighborhood race allows runners to get out and explore the Wicker Park-Bucktown community, and encourages them to patronize area businesses—which are listed and highlighted on the race map—once they’ve crossed the finish line. It’s an opportunity to shop small, buy holiday gifts, and treat yourself for a run well done, and in the case of the neighborhood dispensary, it’s an opportunity to find a much-needed mellow amidst the holiday hoopla.

Wolfbait & B-Girls
Wolfbait & B-Girls

Logan Square
Described as a “local makers marketplace” and filled to the brim with feminist apparel and funky accoutrements, Wolfgait & B-girls has been a longtime cornerstone in the Logan Square shopping community. The eclectic women-owned boutique features all locally made gifts, art, and accessories, from earrings and Krampus ornaments to Chicago-themed coasters, stickers, candles, shirts, and more. Always a go-to shopping spot, Wolfbait is also participating in a neighborhood punch card program designed to foster economic impact for Logan Square small businesses. Happening through the end of December, with cards available for pickup at stores like Wolfbait, shoppers can get them punched by making purchases in-store. Along with Wolfbait, participating businesses include City Lit Books, Fleur, Boulevard Bikes, and The Logan Theatre. Once you’ve made at least 10 punches, you can drop off your card at Wolfbait for a chance to win prizes like movie passes, gift cards, bottles of whiskey, coffee beans, and paint parties at Pinot’s Palette.

Filipina-owned small businesses take the spotlight at a special Small Business Saturday market being held at Brewpoint Craft cafe in Elmhurst. Held from 10 am - 2 pm, the free-to-attend event will be loaded with indie vendors slinging everything from gourmet goodies and candles to jewelry, apparel, and art. Participating businesses include hand-embroidered accessories from Chicago for Keeps, handmade soy wax candles from IM Home Candles, party-planning items from Rae Lou Creative, and artwork from Jackie Andres.

West Englewood
“Flowers that empower” are in full bloom at Southside Bloom, a self-described “farm-to-vase” floral shop emphasizing sustainability and community. All of the lustrous, bouquet-worthy flowers in the Black-owned store are plucked from the surrounding community, with all purchases serving to support jobs for at-risk youth. So whether you’re handpicking a holiday wreath or wooing your partner with a dozen roses, these are florals you can feel especially good about. Even better? Governor Pritzker and the Illinois Department of Commerce and Economic Opportunity recently added Southside Blooms to the Illinois Made program, a statewide collective of independent small businesses worthy of celebration and travel for their unique products and experiences.

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Matt Kirouac is a travel writer with a passion for national parks, Disney, and food. He's the co-founder and co-host of Hello Ranger, a national parks community blog, podcast, and app. Follow him on Instagram.