Just a ten-minute cab ride from Polo and Prada on the Windy City's gold coast is the much funkier, but hardly less chic enclave of Bucktown. In recent years, this quiet neighborhood north of Wicker Park has become home to artists, pioneering shop owners, and up-and-coming chefs who have created an eclectic mix of stores and restaurants along North Damen Avenue. Exploring the area starts at Toast (breakfast, $20), where crowds line up for the Veggie Eggs Benedict, and the French Toast Orgy, so hearty it comes with a steak knife. Then the shopping begins, with Virtu, which sells exquisite, handmade items like colorful glass bowls ($260-$400) by Vermont glassmaker Nicholas Kekic and bird's-eye maple cutting boards ($70-$150) from Wisconsin craftsman Edward Wohl. For sleek leather desk accessories, as well as handbags, bar stools, and other furnishings, there's Stitch. We loved the Italian bentwood chair ($500), a minimalist gem. The Asian antiques at Pagoda Red are equally impressive, particularly the massive Tianwu "scholars' stones" from Guangxi Province (from $880). Bucktown's good taste extends to fashion too: The men's store Apartment Number 9 is the place for Paul Smith, Coast, Theory, and Nicole Farhi plus a smart assortment of woven ties by Lee Allison ($85 each). Cult-favorite T-shirts by 3 Dot are the big draw at the women's boutique Tangerine, but don't leave without twirling through the racks of whimsical corset dresses by Nanette Lepore (from $200) and classic cotton pants by Trina Turk (from $160). For little ones, PsychoBaby sells "cool, crazy kids' stuff" (that's the motto), like a T-shirt with an image of Che Guevara. But there are plenty of sensible things like wooden toys from Melissa & Doug and Birkenstocks for tiny toes. After working up an appetite, join the locals at Caffe De Luca (dinner, $25) for homemade pizza and bruschetta and the neighborhood's best espresso. For dinner we had cassoulet at Le Bouchon, a cozy (and cramped) French bistro we'd heard was the best in Bucktown. Frankly, it wasn't up to snuff—but Spring (dinner, $90) definitely was. In a 1910s Russian bathhouse complete with Zen garden, Shawn McClain makes stunning New American dishes with an Asian flair. Afterward, have a nightcap at Café Absinthe, with its great selection of Scotches and Cognacs, or on the heated patio at Meritage Café and Wine Bar, which pours more than 20 vintages by the glass.
Virtu At 2034 N. Damen Ave.; 773-235-3790.
Stitch At 1723 N. Damen Ave.; 773-782-1570.
Pagoda Red At 1714 N. Damen Ave.; 773-235-1188.
Apartment Number 9 At 1804 N. Damen Ave.; 773-395-2999.
Tangerine At 1719 N. Damen Ave.; 773-772-0505.
PsychoBaby At 1630 N. Damen Ave.; 773-772-2815.
Toast At 2046 N. Damen Ave.; 773-772-5600.
Caffe De Luca At 1721 N. Damen Ave.; 773-342-6000.
Spring At 2039 W. North Ave.; 773-395-7100.
Café Absinthe At 1954 W. North Ave.; 773-278-4488.
Meritage Café and Wine Bar At 2118 N. Damen Ave.; 773-235-6434.