Chicago: Where to Shop: Overview

You’ll find the usual array of luxe labels—Gucci, Chanel, Prada, Cartier, Bulgari, Hermès and the like—along the Magnificent Mile (www.themagnificentmile.com), the famous eight-block stretch of North Michigan Avenue in the area known as the Gold Coast. (Many are concentrated at the 900 Shops at 900 North Michigan Avenue, which also houses notable newcomers Preggers and Galt Baby.) For distinctive local shops, explore the nearby side streets: East Oak (Ultimo), East Walton (Sabbia, Samantha Chicago) and North Rush (Ikram). Ideal for a shopping lunch break is RL, on East Chicago next to Ralph Lauren.

Fashionistas may want to venture to Bucktown & Wicker Park, an up-and-coming destination with a handful of great boutiques, including Helen Yi and P45. Much like New York’s Meatpacking District was when it was just starting to gentrify, the area is still a little rough around the edges. (Overheard: Perky shopper to man walking past with mastiff: “Is your dog friendly?” Man: “Not particularly.”) The best shops are concentrated on North Damen Avenue between North Milwaukee and Armitage; most are open from 11 a.m. until 6 or 7 p.m. Tuesday through Sunday and closed on Monday. Refuel with some sweets at Hot Chocolate or take an early dinner post-shopping at Le Bouchon.