Chicago

Where to Shop: The glories of the Magnificent Mile, Chicago’s main shopping drag, are widely known, but a few miles west in hipster-heavy Wicker Park sits a sizable crop of edgier fare. Habit (1951 W. Division St., 773-342-0093, www.habitchicago.com ) favors emerging designers like local talent Abigail Glaum-Lathbury; a couple of doors down, Renegade Handmade (1924 W. Division St., 773-227-2707, renegadehandmade.com) sells affordable, unique artwork alongside vintage denim and dresses. On the same strip, you’ll find Silver Moon (1755 W. North Ave., 773-235-5797, silvermoonvintage.com), a resale store with an impressive selection of apparel dating back to the late 1800s.
Where to Stay: The Ruby Room (1743–45 W. Division St., 773-235-2323, rubyroom.com) is a day spa/salon/yoga studio that’s added eight well-appointed guest rooms