Before sleek CB opened, you couldn’t find designer pieces by MM6, Theyskens for Theory and Sass & Bide anywhere in Chicago’s hip suburban North Shore area. Thank goodness that nightmare’s over.
Antique 19th-century wedding dresses get top billing here, but the real pull is the racks up front, full of gorgeous, big-event gowns.
The concept of this store is simple and self explanatory. Keep in mind that the store is open...sometimes.
A giant oak library counter and antique card catalogs make it feel like a study, appropriate since Greer is exclusively devote to exquisite stationary, journals and pens.
Devoted to antiques and up-and-coming furniture and industrial designers, it sits in a warehouse-size space but feels thoroughly intimate, thanks to expertly arranged mini areas.
Within the store's eccentric selection, you can stumble upon an array of furs and beautiful dresses.
Known for its affordable cornucopia of clothes, the shop hosts fun midnight sales that attract flocks of fashionable people.
It bursts with glamorous gold jewelry, silk dresses and sultry perfume bottles.
This subterranean space specializes primarily in vintage jewelry: the expansive selection is well sorted and well priced, which means you can snap up a great turquoise ring for $40.
It may be a big antiques mart, but everything here feels special and handpicked: There's an entire case of owl medallions, plus design classics, like George Nelson clocks and Paul McCobb desks.
A recent trip to this expansive antiques mall turned up both a Coogi sweater from the '80s and a rainbow's worth of Bakelite bracelets.
The racks are dotted with pristine vintage picks, like delicately patterned shirtdresses and ballet-hued silk tops.
It’s one of Chicago’s big success stories, so it’s no surprise that the Eskell flagship is equally cool with its beautifully patterned in-house line and an array of well priced labels like Minkpink.
It may be helmed by a J.Crew veteran, but there’s nothing preppy about Roslyn: Romantic one-off tops by Luxury Jones hang next to Christina Hattler dresses.
The bricks-and-mortar outpost of the famous crafts fair of the same name, this tiny store is packed with handmade things, including adorable stationery and cute canvas totes.
Occupying a garage-like, sun-drenched corner in the Meatpacking District, this looks like a gallery at first. Closer inspection reveals paper-thin, bright orange serving bowls and baskets from Mali.
Located just off the primary downtown shopping stretch, Sarca is well worth seeking out: Avant-garde Vivienne Westwood dresses mingle with Grey Ant denim trousers and spiky Camilla Skovgaard heels.
Moodily lit and decked out in foliage, this flower shop/gift store feels extravagantly lush, just like its handmade, embroidered necklaces and artisanal candles.
Though it’s officially situated in the burbs, Chalk has a citified feel. Patchwork Chris Benz skirts hang next to slick black pants (artfully turned out by Olivier Theyskens for Theory).
This home goods spot looks like an English countryside antiques shop that’s had a run-in with a Native American trading post. Highlights include footstools upholstered in iconic Hudson Bay prints.
Hotel silver, historic Queen-emblazoned ashtrays from the U.K. and a smattering of ephemera add up to P.O.S.H.’s enduringly great Parisian-flea-market feel.
Slightly retro, preppy standards by labels like A.P.C. set the tone here—while checkboard floors and midcentury-modern fixtures contribute to its schoolhouse vibe.
A mecca for toy enthusiasts, Rotofugi partners with local artists to produce limited-edition, anime-inspired figurines that are sure to be collectibles.
There’s an large array of Missoni home goods at this accessories emporium, but it finds good company with the equally luxe-feeling, well-priced handbags by Carla Mancini and woven Presh bracelets.
At this store devoted to all things garden-related, you should definitely pay special attention to the wildly cool (and packable) terrariums, peopled with hilarious miniature figurines.
On the fifth floor of a mall, this spot feels like a well-kept secret: Coffee-table books, rare European beauty products, cashmere sweaters and a smattering of cool antiques set the eclectic tone.
This new below-ground spot is a street-inspired concept shop: Christopher Kane T-shirts, Alexander Wang sunglasses and Dee and Ricky Lego brooches abound.
When it comes to a subtly bohemian aesthetic—served up via Gary Graham’s asymmetrical dresses and exotically tinged jewelry—Robin Richman always gets the city’s top honors.
This was one of our favorite boutiques in the country when Lucky launched more than a decade ago: It’s still spot-on, offering labels like Winifred Grace, Lizzie Fortunato Jewels and 3.1 Phillip Lim
The emphasis here is on costume jewelry, all arranged in the center of the store, but the bordering racks deserve a look too, since they’re lined with vintage party dresses, many from coveted names.
Styled like an ’80s Afro-pop parlor, this newcomer specializes in wildly well-priced vintage pieces (it’s hard to find anything that tops $40), including grandpa cardigans and Swatch watches.
Tucked away on a quiet stretch near DePaul University, Kaveri focuses on slightly adventurous cuts, like cropped Rag & Bone bombers and slouchy Demy Lee cashmere sweaters.
Everyday wearable underpinnings—that are still undeniably pretty—are consistently stocked at this Chicago institution.
Helen Yi has been one of Chicago’s fashion pacesetters for nearly a decade, and somehow it’s lost none of its edge: Gorgeously tailored Derek Lam blazers mingle with feminine blouses by Barbara Bui.
There’s an offbeat vibe here: The wallpaper-wrapped room hosts cool drawings by locals and racks are dotted with pristine vintage picks, like delicately patterned shirtdresses and ballet-hued silk top
A maze-like array of cases, packed with blown-glass vases, enamel Chicago charms and prints from the ’60s, makes it easy to spend a whole afternoon here.
This is the best spot in town for avant-garde labels—Dries Van Noten, Marni—and equally forward finds, like Nicholas Kirkwood heels.
Mention Lucky to save 30% on everything (through Dec. 20) at this always satisfying and affordable boutique, packed with pieces from Doma, James Jeans, Susana Monaco and much, much more. Read more.
Slouchy leather satchels and dark clothes with cool detailing (pleats, ruching, and elbow patches) are why this local designer is a standout. Through Dec. 20, save 30% by mentioning Lucky. Read more.
This shop has long been a staple for beautiful basics as well as essential accent pieces, like over-the-knee boots from Joie. Save 30% through Dec. 20 by name-dropping Lucky. Read more.
Arguably offers one of the city’s best waxes, thanks to the all-natural wax Épilyss. Through Dec. 20, save 50% on the Brazilian Bikini Wax by mentioning Lucky. Read more.
This salon has two locations in the city, both conveniently open until 9 pm during the week, so getting a cut, a deep-conditioning treatment, or a blowout is easier than ever.
Frei Designs creator Annie Novotny offers her full collection of eco-conscious, classic-with-a-twist clothes, as well as the lines of favorite indie designers, like Brooklyn-based Loup Charmant.
Designer Ashley Zygmunt, a recent grad of the Chicago Fashion Incubator project, just opened this shop, where browsing is appointment-only. Read more.
Many fantastic local designers are on the roster at this new shop like Jules, Kate Boggiano, and Nora Del Busto. Read more.
Beautifully crafted home goods and accessories make this spot a favorite general gift store of sorts. Read more.
Colorful gems are the focus of this designer who creates her own collection of pieces but encourages you to DIY at her in-boutique gem bar. Read more.
We’re not sure what we love most at this haven for all things home: the flea market, the garden, or the indoor furniture and accessories. Read more.
This younger cousin of old-guard Winnetka boutique Frances Heffernan stocks pieces that have a sense of quiet luxury. One perk of shopping here is the in-house alteration department. Read more.
This mom-and-pop store closes for two months at the start of every year while the owners take a buying trip to a far-flung locale. They come back with amazing finds, most under $40. Read more.
Occupying a former gallery, the concrete-floor-clad space is a fitting backdrop for elegantly cool labels that are hard to find elsewhere. Read more.
A modern Hollywood Regency look is a fitting setting for elegantly tailored picks (many of which are exclusive to the store) from designers like Sea and Adam. Read more.
This upscale standard has long been known as the place to zero in on high-end-but-experimental talents. Our favorite reason to visit: its wait-list-worthy selection of shoes. Read more.
