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, ravenswoodantiquemart.com
4727 N. Damen Ave., 773-271-3700, ravenswoodantiquemart.com
Renegade Handmade
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.
1924 W. Division St., 773-227-2707, renegadehandmade.com
1924 W. Division St., 773-227-2707, renegadehandmade.com
Robin Richman
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.
2108 N. Damen Ave., 773-278-6150, robinrichman.com
2108 N. Damen Ave., 773-278-6150, robinrichman.com
Roslyn
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, roslynboutique.com
2035 N. Damen Ave., 773-489-1311, roslynboutique.com
R.S.V.P. Gallery
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.
1753 N. Damen Ave., 773-770-6666, rsvpgallery.com
1753 N. Damen Ave., 773-770-6666, rsvpgallery.com
Sarca
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, shopsarca.com
710 N. Wabash Ave., 312-255-0900, shopsarca.com
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, silvermoonvintage.com
1721 W. North Ave., 773-235-5797, silvermoonvintage.com
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, space519.com
900 N. Michigan Ave., 312-751-1519, space519.com
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, sprouthome.com
745 N. Damen Ave., 312-226-5950, sprouthome.com
Stitch
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 (but well-priced) handbags by Carla Mancini and woven Presh bracelets.
1723 N. Damen Ave., 773-782-1570, stitchchicago.com
1723 N. Damen Ave., 773-782-1570, stitchchicago.com
