• Buck the norm in Bucktown and Wicker Park
• Discover the city’s leading-edge fashion boutiques
• Refuel with the perfect cheeseburger or an elegantly crafted cocktail

A generation ago, Wicker Park and Bucktown were decidedly on Chicago’s periphery, inhabited mostly by immigrants and cash-strapped artists. Then came the 1990s, when indie-rock acts like Liz Phair and the Smashing Pumpkins put this scruffy enclave on the national map—setting forth a tide of hipsterfication and rising rents. While the area isn’t as gentrified as, say, NYC’s Williamsburg, plenty of high-end chains have moved in (Alexis Bittar; Cynthia Rowley; Aesop). Thankfully there are still only-here shops like Moon Voyage, overseen by Chicago native Susie Lee, whose sensibility hangs somewhere between the East and West Coasts (right around Illinois, we’d say). With boho-chic women’s clothing and accessories, Korean beauty products, and design items for the home, it’s the one-stop that sums up the ’hood. A few blocks up Damen Avenue, you’ll find P.45, founded in 1997, where Tricia Tunstall continues to curate a provocative-yet-tasteful mix of established and emerging designers. Further north on Damen is RSVP Gallery, an edgy streetwear boutique owned by Kanye West’s style consigliere, Virgil Abloh. And on Division Street, Penelope’s specializes in “underrepresented” labels for men and women, as well as shoes, accessories, and a sizable range of clothing from French sensation A.P.C. For a pick-me-up between shopping stops, we love the gooey cheeseburger at Small Cheval (a spin-off of the legendary Au Cheval in West Loop); the chorizo tacos at Big Star; and the pistachio-lemon donuts at Stan’s. Or, if it’s after 6 p.m., hit the Violet Hour for one of Chicago’s best-made cocktails.

Wicker Park and Bucktown are roughly 20 minutes by taxi from the Conrad Chicago; North Damen Avenue is the main shopping thoroughfare running through both.

MOON VOYAGE: 2010 W. Pierce Ave.; 773-423-8853;

P.45: 1643 N. Damen Ave.; 773-862-4523;

RSVP: 1753 N. Damen Ave.; 773-770-6666;

PENELOPE’S: 1913 W. Division St.; 773-395-2351;

SMALL CHEVAL: 1732 N. Milwaukee Ave.;

BIG STAR: 1531 N. Damen Ave.; 773-235-4039;

STAN’S DONUTS: 1560 N. Damen Ave.; 773-360-7386;

THE VIOLET HOUR: 1520 N. Damen Ave.; 773-252-1500;