The Best Shopping in Chicago

From the glitzy shops on North Michigan Avenue’s Magnificent Mile, you may be led to believe that Chicago is all about labels, department stores, and glamour, but scratch the city’s surface and you’ll find a wealth of antiques, bookstores, home decor, vintage boutiques, housewares, and independent designers that make Chicago a little-known shopping destination.

1528 N Milwaukee Ave # 1, Chicago, IL 60622, USA
It’s always been about affordable vintage goods at this Wicker Park boutique, which sells contemporary dresses and tops from Amuse, men’s hats from Brixton, denim from skinny-jean pros Just USA, rompers from Los Angeles–based En Crème, and handcrafted leather boots from Red Wing. The popular shop’s homewares and apothecary section is arguably the best place to pick up gifts your friends will love, from grooming and shaving goods to candles, perfumes, and barware like flasks and cocktail shakers.
851 W Randolph St, Chicago, IL 60607, USA
This skin-care sanctuary just opened its doors in Fulton Market’s bustling neighborhood after spending two years in Roscoe Village, where it built an obsessive following for its handmade products. The line was inspired by the cofounders’ mission to create items free of parabens, sulfates, and dyes, and to date they’ve already whipped up soaps, scrubs, masks, and body butters. If that wasn’t enough to keep them busy, the shop also runs several wellness classes a week (including yoga and meditation), along with a six-seat mask bar, where guests can customize their own clay masks with the guidance of skin-care pros.
2327, 833 W Washington Blvd, Chicago, IL 60607, USA
Chances are you’ve seen Maria Pinto’s works at some point in recent years—she’s known for dressing the likes of First Lady Michelle Obama, Oprah Winfrey, and Brooke Shields. That fan base is only growing with the opening of her West Loop Style Studio, where women can shop M2057 by Maria Pinto, a ready-to-wear collection inspired by urban architecture and design. Created for the time-pressed but fashion-forward woman, Pinto’s pieces marry runway ideas with a low-maintenance aesthetic (the upscale fabrics might be imported from Italy, but they’re also machine-washable and wrinkle-resistant—perfect for travel). In addition to plenty of day-to-night options like dresses, skirts, tops, and pants, the boutique also carries belts and jewelry by outside artists, curated by Pinto.
1511 West Berwyn Avenue
Teenage Mutant Ninja Turtles T-shirts, Members Only jackets, Beavis and Butthead outerwear, Max Headroom sunglasses… oh yes, these are all the droids we’re looking for. Visitors on the hunt for totally tubular leg warmers, an acid-washed jean jacket, and a Michael Jordan bobblehead need look no further than Rad Vintage, supplying all the vintage toys, clothing, videos, and accessories that our inner kids could ever dream about. It’s one of the biggest vintage stores in Andersonville; the merchandise is in spectacular condition, and the prices are reasonable. It’s rad, man.
5219 N Clark St, Chicago, IL 60640, USA
Brimfield specializes in antique glassware, vintage signs, custom upholstered chairs and plaid blankets, pillows and furnishings of every conceivable style and design. The owners began collecting antiques in the UK in the late 1990s and opened their shop in Chicago about 8 years ago. Brimfield continues to be family owned and operated and they promise unique finds to all their customers.
1472 N Milwaukee Ave, Chicago, IL 60622, USA
This charming little store on Milwaukee is stuffed with vintage goods in primo condition. Beautiful chunks of costume jewelry and frilly fascinators share space with lush leather handbags and sparkling glassware. Nothing in the store is cheaply made—or priced—but all of the items are carefully selected for maximum appeal and quality. Shoppers who come in to browse will likely find treasures they simply can’t live without, because Store B Vintage has some of the prettiest retro pieces in the city.
3020 N Lincoln Ave, Chicago, IL 60657, USA
Like most good thrift stores, the Brown Elephant is hit or miss. Sometimes you can find great books, T-shirts, and super-cheap vinyl—other times, nothing appeals, and you just wander around until your feet hurt. This shop is well organized, and most of the home goods are reasonably priced. All of the proceeds go to benefit the Howard Brown Health Center, a great LGBT charity; if you’re waffling on spending a couple extra bucks, just go for it and know that your money is going to help someone who needs it. (The Brown Elephant has three outlets: this one in Lakeview, one in Andersonville, and one in Oak Park.)
2780 N Lincoln Ave, Chicago, IL 60614, USA
This Lincoln Park destination, besides being one of the only designer-toy shops in the Midwest, has gained a reputation for being one of the best designer-toy shops in the world. It stocks a wildly diverse selection of vinyl figures and pop-culture collectibles from creative brands across the globe, including Kidrobot, Funko, Tokidoki, and Amuse. Still, it’s their “blind box” toys that sell fastest—customers don’t know which toy in a collection or series they’re buying until they open the box post-purchase. The shop’s other areas come with surprises, too: An adjacent gallery houses artwork, and its 1,000-square-foot space is available for private events (when it’s not hosting monthly BYOB Drink n’ Draw parties).
2850 N Lincoln Ave, Chicago, IL 60657, USA
Brimming with all things pulp and ink, and oozing the olfactory enjoyment that is ‘old book smell,’ Powell’s Bookstores are a Chicago institution. Focusing on academic and scholarly works for the past four decades and counting, their three locations are your literary oasis in the bustling city of Chicago. From newly written works, to those hard-to-find tomes, Powell’s is steeped in a plethora of choices guaranteed to please all. The Lakeview location pictured above is staffed by incredibly knowledgeable folks, and even has a sitting area in front for reading, or that random game of chess that may break out at any time because of the pre-populated board that is always at the ready.
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