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It’s time to talk shop. Whether you have a dozen trendy gal pals, hipster cousins, or tradition-loving in-laws, these city-specific guides to the Best Holiday Shopping will solve all your gift-giving dilemmas.
Best Holiday Shopping in....
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Best Holiday Shopping

Chicago

Hot & Cool

Seemingly unscathed by the economic turndown, the North Side neighborhood of Andersonville bustles day and night, and over the past three years it has become a bona fide home furnishings destination. Start at Scout (scoutchicago.com), owner Larry Vodak’s homage to found and vintage accoutrements, which include everything from barstools to dressers to antique library catalogs. Across the street, fixtures and furniture made from sustainable materials cement the top-shop reputation of Urbanest (urbanestliving.com), where bamboo flooring and cherry-wood tables impart a modern Asian feel. Smaller gift items attract shoppers to City Olive (cityolive.com) for more than 30 types of olive oil, and to Paper Trail for stationery and cheeky gag gifts. The similarly trendy Southport Corridor shopping district, a short walk from Wrigley Field, is girly-boutique central. The lingerie and swimwear shop Trousseau prides itself on expert bra sizing, while Krista K (kristak.com) keeps up with runway styles from Theory, Vince, and Rebecca Taylor.

Hip

Retail options go against the grain in Wicker Park, where you’ll find the perfect gift for your art-student sister or bike-messenger cousin. A launching pad for emerging designers, Habit (habitchicago.com) stocks handbags, jewelry, and clothing in minimal quantities, so you’ll never have to feel part of the mainstream. Similarly funky Paper Doll (paperdollchicago.com) carries gorgeous stationery and decidedly un-Hallmark greeting cards. For the bambinos in your life, Grow Kids’ (grow-kids.com) selection of gear and clothing for tykes (Bloom highchairs, Clover New York dresses) favors the modern and minimal. Next, stray from the beaten path to find a convivial mix of Mexican culture and avant-garde retail in the South Side Pilsen neighborhood. Mestiza (mestizachicago.com) displays Day of the Dead skulls and Jesus statues alongside pretty shawls from Ecuador. And at Workshop (workshopchicago.com), designer Annie Novotny of Frei Designs sells dresses, jackets, and pants, all interestingly inspired by Victorian mourning clothing.

Classic

Both big-box department stores and indie boutiques nestle in the skyscraper shadows of Chicago’s ever-popular Loop and Magnificent Mile shopping districts. In December, the tiny timber cabins of the traditional German Christkindlmarket (christkindlmarket.com) open near the busy corner of State and Washington streets, serving everything from hand-blown glass ornaments to Russian nesting dolls to wienerschnitzel. One block east, a giant fir tree towers in the wood-paneled Walnut Room restaurant at Macy’s (macys.com), where shoppers graze on soups and salads before buying classic Chicago souvenirs such as Frango Mints. Nearby, the Chicago Architecture Foundation shop (architecture.org/shop) offers Lego’s John Hancock Center construction sets and coffee table books saluting Frank Lloyd Wright, Louis Sullivan, and others that made marks locally. From there, it’s a five-minute walk north to the Magnificent Mile, where the MCA Store (mcachicagostore.org) in the Museum of Contemporary Art skews quirky with talking alarm clocks and Pop Art–influenced home décor. Another historic shopping stretch is Armitage Avenue in Lincoln Park, which houses longtime shops such as Tabula Tua (tabulatua.com), a source of fine china and tableware, and Art Effect (shoparteffect.com), a purveyor of everything from designer threads to paper goods.