The Best Shopping in Chicago
Collected by Nicole Schnitzler , AFAR Local Expert
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.
1643 N Damen Ave, Chicago, IL 60647, USA
Tricia Tunstall opened the doors to this Bucktown boutique back in 1997, which makes it a pioneer in the neighborhood for its upscale and diverse design lineup in women’s apparel. That roster features tops, dresses, bottoms, shoes,...
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...
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...
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...
2136 W Fulton St unit j, Chicago, IL 60612, USA
The inspiration for this Chicago-based apparel retailer came from the desire to make timeless, hardy menswear at the right price—and in the United States. As such, its pieces range from button-down sports shirts and heavy-duty-denim work...
1870 N Damen Ave, Chicago, IL 60647, USA
This Bucktown lifestyle boutique carries everything for the home, closet, and beyond—and at an affordable price point to boot. Owner Emily McKenney curates an inventory focused on Chicago designers (Le Coeur, Sophia Reyes, Ali's Collection,...
1913 W Division St, Chicago, IL 60622, USA
Founded by a husband-and-wife team in 2002, this Wicker Park boutique specializes in goods crafted by independent creators, with both local and international viewpoints represented. The styles are attractive and accessible, with an...
934 W Armitage Ave, Chicago, IL 60614, USA
This shop has been supplying Lincoln Park tastemakers with the finest jewelry, women’s clothing, home decor, stationery, and gifts since 1984—all at a range of price points and styles. Today, those items include the works of jewelry...
1432 W Chicago Ave, Chicago, IL 60642, USA
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...
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...
1854 W North Ave, Chicago, IL 60622, USA
Quimby’s says they specialize in “unusual publications, aberrant periodicals, saucy comic booklets and assorted fancies” and if that description doesn’t grab you, then this isn’t your kind of place. However, if this is your kind of place then you...
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...
1379 N Milwaukee Ave, Chicago, IL 60622, USA
Reckless Records specializes in DVDs, vintage vinyl and used CDs of all kinds from Top 40 music to every obscure band that ever put out an album. The workers at Reckless have a reputation for being the tiniest bit elitist and because of that...
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,...
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...
5216 N Clark St, Chicago, IL 60640, USA
Located just two blocks from Wrigley Field, this apparel fun house has been making a name for itself ever since 1983 for its quirky threads (not to mention a solid inventory of Converse Chuck Taylors and whoopee cushions). Once you’re here,...
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...
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