15 E. Oak St., Gold Coast
Going to Barneys in Chicago is kind of a spiritual experience. To start, the buyers at this branch are incredible at finding pieces that you often won’t find anywhere else. A huge plus, because Chicago tends to be more conservative, is that you can actually find runway pieces, as they tend to disappear lightning fast in New York or Los Angeles.
33 E. Oak St., Magnificent Mile
Maybe it’s because it’s so damned cold in Chicago in the winter that the Moncler store here is one of the best in terms of selection. The Italian brand is famous for making winter outerwear, even big puffy jackets, look good.
1885 N. Clybourn Ave., Lincoln Park
This beloved vintage furniture/décor/botany mecca was a major contributor to making the Chicago goop Pop the experience it was. Even if you’re not in the market for say, a crushed velvet fainting sofa or crystal chandelier, perusing the bright space is an inspiring experience. Can’t do in-person? The online shop is the next best thing.
1013 W. Webster Ave., Lincoln Park
After years of putting her MBA to good use as an ad exec, Chandra Greer left it all behind for more creative pastures and never looked back. Greer is the kind of stationery-slash-gift shop you can pop into in a hurry and emerge with the perfect present (say, a Xenia Taler trivet or Lucia candle) or time permitting, pass an afternoon perusing the artfully cluttered displays. All the usual suspects—Rifle Paper Co., Delfonics, Ferme a Papier—are well represented, as are less-known indie makers like Antiquaria and Tiselle. Don’t miss the house line of miniature just-because cards, aptly called Civilettes.
2029 N. Western Ave., Bucktown
Kelly Whitesell and Elizabeth Del Castillo, the founders of this Wicker Park standby, are known for their trend-driven, yet somehow totally timeless sensibility, which is perfectly reflected in the boutique’s easy-to-navigate layout and eclectic buy (Judi Rosen denim, knits from Barcelona-based Yerse, and In God We Trust charm necklaces). And while the eponymous house line might skew a little young for some, for the right girl, the racks of retro-tinged dresses and printed separates are a sartorial goldmine. The apothecary, however, is a sure bet for just about everyone—think, D.S. & Durga fragrances and Qualitas candles.
2108 N. Damen Ave., Bucktown
With its almost exclusive focus on lesser-known European lines (tiered dresses by Tsolo Munkh, Elena Dawson separates, Guidi boots), this Bucktown shop has been a hit with the avant-garde crowd since the '90s. The airy, welcoming space is really more gallery than store, which makes sense since the buy is largely of the architectural and one-off variety.
Broadway Antique Market
6130 N. Broadway St., Edgewater
Chicago antique malls are the stuff of mid-century modern legend, and BAM is the crème de la crème. At 75-vendors strong (most with a focus on Art Deco, Mission, and Mid Century modern design), it’s got something for everyone. Furniture, clothing, accessories, costume jewelry—all of it blessedly organized so there’s little need to dig. And as locals will tell you (or more likely, not tell you) the semi-annual sales are epic.
RR #1 Apothecary
814 N. Ashland Ave., West Town
Housed in what used to be a 1930s apothecary (thankfully, the original wood paneling was left untouched), RR#1 Apothecary is one of those stores that you’ll have a hard time leaving empty-handed. On offer: a dizzying array of candles, teas, and soaps, as well as kitschy prank gifts, tea towels, and novelty books. It’s pretty ideal for picking up a last minute something for the hostess, they'll even gift-wrap your selection right at the counter.
1440 W. Hubbard St., West Town
This fabled auction house’s claim to fame is organizing modern and contemporary design shows that have the power to bring seasoned collectors to their knees and inspire novices to start investing. In addition to a gallery and consignment department, the Chicago location is home to the Wright Now showroom, which houses globally-sourced décor, furniture, and fine art that can be viewed by appointment.
745 N. Damen Ave., West Town
It’s true that here you’ll find all manner of fresh flowers and gardening tools—they’ll even help black thumbs figure out how to revive dying houseplants—but it’s the custom terrariums that make the original Sprout Home a must-see (there’s a second location in Brooklyn, NY). In addition to botany-related workshops and wedding florals, professional garden-design services (there’s a mini nursery in the back) are also available.