Asrai Garden

Moodily lit and decked out in foliage, this flower shop/gift store feels extravagantly lush, just like its handmade, embroidered necklaces and artisanal candles.

1935 W. North Ave., 773-782-0680,

Barneys New York

Though highly regarded as the ultimate department store, it always takes a chance on emerging labels, often before even the smallest boutiques do. Its Co-op area—our favorite—focuses on young designers.

15 E. Oak St., 312-587-1700,


Housed in a former post office, this expansive boutique is the best spot in town for avant-garde labels—Dries Van Noten, Marni—and equally forward finds, like Nicholas Kirkwood heels.

212 W. Chicago Ave., 312-202-0047


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.

5219 N. Clark St.
, 773-271-3501,

Broadway Antique Market

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.

6130 N. Broadway St., 773-743-5444,

Chalk Boutique

Bringing an urban edge to Chicago's north shore, Chalk carries beautifully made apparel and accessories by such established designers as Nina Ricci, The Row and Chloé. For the fashion enthusiast, Chalk also showcases edgier collections like Isabel Marant and Rosie Assoulin.

2611 Prairie Ave., Evanston, 847-424-0011,

Dovetail Chicago

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 tops.

1452 W. Chicago Ave., 312-243-3100,


It's one of Chicago's big success stories (the label is sold at some of the best boutiques in the States), so it's no surprise that the Eskell flagship is equally cool: Beyond the beautifully patterned in-house line, there's a great array of nicely priced labels like Minkpink.

1509 N. Milwaukee Ave., 773-486-0830,

Edgewater Antique Mall

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.

6314 N. Broadway St., 773-262-2525,


A giant oak library counter and antique card catalogs make it feel like a study, appropriate since Greer is exclusively devoted to exquisite stationery, journals and pens.

1657 N. Wells St., 312-337-8000,

Handle With Care

Originally a small gift shop, this long-standing neighborhood favorite occupies two enormous attached storefronts, and each has a distinct identity. The original space sells prettily packaged candles along with nicely priced tops and dresses; the lofty second chamber adopts a modern exoticism as its theme, with Turkish glass lanterns and color-splashed garments.

1706 N. Wells St., 312-751-2929,

Helen Yi

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.

1725 N. Damen Ave., 773-252-3838,


On Chicago's Gold Coast, Ikram Goldman's laquer red boutique is a beacon for the city's intelligentsia. Past the porthole-like entrance, we delved into lush Lanvin ruffles, sleek Céline frocks, and Marni belts studded with lozenge-like stones. It's no wonder a certain First Lady is a fan.

15 East Huron St., 312-587-1000,

Jayson Home and Garden

We're not sure what we love most at this outstanding haven for all things home: the flea market, the outdoor garden, or the indoor furniture and home accessories.

1885 N. Clybourn Ave., 773-248-8180,


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.

2035 N. Damen Ave., 773-489-1311,


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.

710 N. Wabash Ave., 312-255-0900,


Styled like an '80s Afro-pop parlor, this spunky shop specializes in wildly well-priced vintage pieces (it's hard to find anything that tops $40), including grandpa cardigans and Swatch watches.

1323 N. Milwaukee Ave., 773-252-6996,

Krista K

Krista Kaur Meyers' light-flooded corner store—a onetime insurance office—has an easy-flow split-level layout: The upper half showcases the latest from labels like Elizabeth and James and Helmut Lang (plus a small selection of footwear and accessories); the wares downstairs fall into the more casual, jeans-and-tees camp.

3458 N. Southport Ave., 773-248-1967,

Le Dress

Dresses are the name of the game at this Wicker Park boutique. Find names like Poleci, Hayden-Harnett, Haven, and Grace Sun, plus the wearable in-house line, Denella.

1741 W. Division St.
, 773-697-9899,

Lulu's on the Avenue

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 highly coveted names.

900 North Michigan Ave., 3rd Fl.
, 312-888-9149,

Merz Apothecary

Truly old-world (it's been around since 1875), Merz stocks an intensive array of hard-to-find beauty labels, like 4711 (the world's first cologne) and Badger.

4716 N. Lincoln Ave.
, plus a downtown location, 773-989-0900,

The Mexican Shop

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 jewelry and accessories, most under $40.

801 Dempster St., Evanston, IL, 847-475-8665

Morlen Sinoway Atelier

Occupying a garage-like, sun-drenched corner in the Meatpacking District, this looks like a gallery at first glance. Closer inspection reveals paper-thin, bright orange serving bowls and baskets from Mali.

1052 W. Fulton Market St., 312-432-0100,


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.

1643 N. Damen Ave., 773-862-4523,


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.

1913 W. Division St., 773-395-2351,


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.

613 N. State St., 312-280-1602,

Ravenswood Antique Mart

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.

4727 N. Damen Ave., 773-271-3700,

Robin Richman

When it comes to a subtly bohemian aesthetic—served up via Gary Graham's asymmetrical dresses and exotically tinged jewelry by Arielle de Pinto and Regina Dabdab—Robin Richman always gets the city's top honors.

2108 N. Damen Ave.
, 773-278-6150,


A mecca for toy enthusiasts, Rotofugi partners with local artists to produce limited-edition, anime-inspired figurines that are sure to be collectibles.

2780 N. Lincoln Ave., 773-868-3308,

R.S.V.P. Gallery

This below-ground spot is a street-inspired concept shop: Christopher Kane T-shirts, Thierry Lasry sunglasses and Hood by Air tanks abound.

1753 N. Damen Ave., 773-770-6666,

Samantha Chicago

Done up with chiffon pink shag carpets, milk-glass lamps, and a circular faux-ostrich couch, this boudoir-influenced spot presents clothing as unabashedly feminine as the decor. Missouri native Samantha Mittelman has long been a fan of traditional glamour and has put a modern-day stamp on the aesthetic through her classically flattering picks.

64 E. Walton St., 866-951-5383,

Silver Moon

Antique 19th-century wedding dresses get top billing here, but the real pull is the racks up front, full of gorgeous, big-event gowns.

1721 W. North Ave., 773-235-5797,

Space 519

Sprawled out on the fifth floor of one of Michigan Avenue's main malls, 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.

900 N. Michigan Ave., 312-751-1519,

Sprout Home

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.

745 N. Damen Ave., 312-226-5950,


There's an intensive array of Missoni home goods at this long-standing accessories emporium, but it finds fitting company with the equally luxe-feeling rainbow of Botkier bags and beachy, beaded Chan Luu bracelets.

1723 N. Damen Ave.
, 773-782-1570,


Lori Mandarino and Alex Averbach (mother and daughter) and Erica Cook, owners of Tangerine, are investing heavily in intricately patterned Tibi dresses, Society for Rational Dress blouses, and pearl-studded hoops by local jeweler Coqui.

1719 N. Damen Ave., 773-772-0505,

Veruca Salt

There's a huge range of pieces here, including super-casual picks from James Jeans and Rachel Pally, along with super-feminine dresses and teetering heels from lines like Lauren Moffatt and Sunner.

520 N. Kingsbury, 773-276-9888,

Vintage Underground

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.

1834 W. North Ave., 773-252-4559,


Beautifully crafted home goods and accessories make Virtu a favorite general gift store of sorts, where you can find everything from Ed Wohl breadboards to precious metal rings from Anne Sportun.

2034 N. Damen Ave., 773-235-3790,

The Art Institute And Museum Of Science And Industry

This is the best city for museums. My favorites are the Art Institute and the Museum of Science and Industry. The latter has a permanent fairy castle exhibit, which has nothing to do with science or industry but is awesome. 111 S. Michigan Ave., 312-443-3600; 5700 S. Lake Shore Dr., 773-684-1414

The Adler Planetarium

Another fun thing to do is visit the Adler Planetarium. My friend and I watched a show there recently and listened to David Bowie while it played. 1300 S. Lake Shore Dr., 312-922-7827

Asrai Garden

My friend calls Asrai Garden—a boutique in Wicker Park—a goth gift shop, and that sums it up well. It sells incense, candles, beautiful flowers and really cool rings. 1935 W. North Ave., 773-782-0680

The Bongo Room

There’s also a really good brunch spot in Wicker Park called The Bongo Room. It has Oreo pancakes! 1470 N. Milwaukee Ave., 773-489-0690


A really good book and zine store is Quimby’s. I’ve discovered some of my favorite cartoonists there. 1854 W. North Ave., 773-342-0910


I get my hair done at a salon called Sparrow in Logan Square. They make their own products and are just wonderful. I love it there. 2545 N. Milwaukee Ave., 773-486-9300


During the play’s Chicago run, the cast would usually get dinner at an Italian restaurant called Orso’s in Old Town. It has a piano, a back patio and chandeliers—you kind of feel like you’re in an old-fashioned train car. I always get the arugula pizza. 1401 N. Wells St., 312-787-6604

Magnificent Mile

I’ve been living near the Magnificent Mile and enjoying wandering around there—visiting Topshop, American Apparel and all those big stores. I’ll go to Lush and buy a whole bunch of bath bombs. 830 N. Michigan Ave., 312-280-6834; 46 E. Walton St., 312-255-8360; 835 N. Michigan Ave., 312-573-1805

Tavi Gevinson's Guide To Chicago

Tavi Gevinson—writer, singer, editor and star of the Broadway play This Is Our Youth—tells us where to score unique jewelry, munch on Oreo pancakes and discover cool zines.