Chicago Local Life

The Best Chicago Neighborhoods for Shopping Small

Small Business Saturday celebrates local mom-and-pop shops and independently owned stores. Traditionally held the Saturday following Black Friday—a day dominated by big-box stores and chains—this year’s Small Business Saturday falls on Nov. 24. If you want to get out and support local stores, you have plenty to choose from in Chicago. Many Chicago neighborhoods have walkable shopping districts filled with local businesses.

Here are five of the city’s best.

26th Street — Little Village

Although each of Chicago’s neighborhoods has a unique character, finding the borders separating them can be tricky. This is not the case with Little Village. A sweeping terracotta archway emblazoned with the worlds “Bienvenidos a Little Village” ushers you into the neighborhood. If you’re looking to do some shopping, the neighborhood’s two-mile stretch, unofficially known as the “Mexican Magnificent Mile,” has more than 500 local businesses. 

Places to Shop:

  • La Baguette Bakery - Come here to add a little fuel to your shopping trip with fresh-baked bread and cakes.

  • Village Discount Outlet - Serious thrifters search for hidden treasures in this three-floor second-hand store.

  • A.M. Goods - All Mexican Goods, a family-owned business, sells custom piñatas, decor, and cookware.

Armitage Avenue — Lincoln Park

Lincoln Park is characterized by beautiful brownstones, and it’s known as the home of DePaul University’s campus. With access to the lake and the Lincoln Park Zoo, this neighborhood is a lovely spot to spend a Chicago day outdoors. When it comes to Small Business Saturday shopping, venture onto Armitage Avenue, where you’ll find everything from designer clothes to musical instruments.

Places to Shop:

  • All She Wrote - A charming stationery store dedicated to the art of writing with a friendly shop dog.

  • McShane’s Exchange - Find designer labels at consignment shop prices at McShane’s, open in the neighborhood since the late 1980s.

  • Old Town School Music Store - Right off the Armitage Purple and Brown Line station, this nonprofit music store sells musical instruments and gear.

Clark Street — Andersonville

Andersonville is known for its Swedish heritage and some businesses, like the Swedish American Museum and Svea, still carry the torch for the neighborhood’s past. It’s also one of the best spots in Chicago for shopping small. Almost all of the businesses open on Clark Street, the neighborhood’s main commercial thoroughfare, are independent and owned by locals, including many of the coffee shops and cafes.

Places to Shop:

  • The Brown Elephant - Pro tip: You can negotiate prices at this secondhand store specializing in furniture and home goods. Proceeds go to LGBTQ healthcare.

  • Women & Children First - A neighborhood stalwart feminist bookstore, with in-store readings, unusual children's books, and friendlier staffers than that “Portlandia” sketch. 

  • Brimfield - It's like a Wes Anderson film come to life in this store specializing in upholstery, vintage home goods, and Midwestern kitsch.

Lincoln Avenue — Lincoln Square

Similar to Clark Street’s quaint Main Street vibe, Lincoln’s Square’s walkable commercial corridor feels like stepping back in time. 

Neighborhood anchors include the Old Town School of Folk Music, which hosts concerts and classes, and the Davis Theater, which has a historic facade but modern amenities and current box office hits. Sprinkled throughout Lincoln Avenue are charming restaurants and cafes, like the cozy Bistro Campagne and Oromo Cafe, known for creative lattes made with superfoods. 

The Chamber of Commerce, which also encompasses neighboring Ravenswood, celebrates Small Business Saturday by hosting a tree lighting, ice sculptures, and Victorian caroling.

Places to Shop:

  • The Chopping Block - Anyone with culinary aspirations will appreciate the kitchen supplies at this Lincoln Square spot.

  • Merz Apothecary - An old-fashioned pharmacy brimming with all-natural brands, high-end men’s grooming products, and perfumes in luxe bottles.

  • Savory Spice Shop - Find classic and uncommon spices here for holiday baking and cooking. 

Milwaukee Avenue — Wicker Park

Wicker Park is top-of-mind for anyone seeking a neighborhood that oozes urban cool; it’s packed with trendy bars and restaurants. Although Milwaukee Avenue has seen the arrival of many high-end chains over the years, you can still find local retail that harkens back to the neighborhood’s grungier past.

Essential to any day of shopping is access to lots of spots for refueling, and Wicker Park has that. The nerdy Werewolf Coffee—technically in Bucktown—is a neighborhood favorite, and newcomer Fairgrounds gets hipster cred with lots of plants and avocado toast.

Places to Shop:

  • Reckless Records - Add to your LP collection with new and old finds at this staple for Chicago vinyl collectors.

  • Vintage Underground - An impressive collection of costume jewelry caters to both the casual browser and serious collector.

  • Myopic Books - The slightly musty but always comforting smell of books envelops you in the winding stacks of this used book store.

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