Michigan Avenue -- specifically the stretch between the Chicago River and Oak Street Beach known as The Magnificent Mile -- is pretty much synonymous with Chicago shopping. Along this 14-block promenade you'll find all the major names in upscale retail (Tiffany & Co., Ralph Lauren, Louis Vuitton, etc.), along with more mass-market stores such as The Gap, Pottery Barn, and Crate & Barrel. High-rise indoor malls, including Water Tower Place (835 N Michigan Ave), Chicago Place (700 N Michigan Ave), and 900 North Michigan, expand the shopping possibilities and make good stop-offs during chilly and/or rainy weather.
But to see the best of what Chicago has to offer, you'll have to move beyond this tourist-clogged thoroughfare. You should head to Armitage Avenue in Lincoln Park or Bucktown to see where the best-dressed locals do their shopping. Chinatown on the city's South Side is a great place to find antiques, jewelry, art, and other quality goods.
Insider's Guide: The Best of Shopping in Chicago
The boutiques on Armitage Avenue between Halsted Street and Damen Avenue attract stylish young professionals with a mix of home decor, beauty products, and trendy-but-not-too-edgy fashion. Lori's Designer Shoes (824 Armitage Ave) has 5,000 square feet filled with shoes ranging from summer sandals to knee-high leather boots. Accessories like handbags, scarves, hats, and hosiery can also be bought, and you'll find them all reduced more than 50 percent at end-of-the-season sales. Your best bet is to go on weekdays, when crowds are more subdued.
If you're looking for something more cutting-edge, head to Bucktown, specifically the shops that line Damen Avenue north of North Avenue. Here you'll find a range of independent clothing stores specializing in new, up-and-coming designers, as well as boutiques that stock one-of-a-kind home accessories and gifts. If you're shopping for little ones, be sure to visit The Red Balloon (2060 N Damen Ave), a friendly mid- to upscale kids clothing, toys and book shop.
Head south on Damen Avenue to reach the newest burgeoning retail district at West Division Street (west of the Division L train stop on the Blue Line). Here, drawn by the relatively low rents, independent boutiques are springing up, offering an eclectic selection of clothes and gifts. For more eclectic boutiques, record stores and book stores, head southeast along Milwaukee Avenue for stores like Reckless Records, American Apparel, and John Fluevog Shoes.
Home decorating fans should also take time for a stroll through River North, with its dense concentration of design stores. Within a few blocks, you'll find everything from slick European contemporary furniture to Asian antiques to affordable reproductions of classic modern pieces.
900 North Michigan Shops (900 N Michigan Ave) has more than 70 shops, including Bloomingdale's and Gucci, surrounding a marble atrium. Crate & Barrel (646 N Michigan Ave) is a flagship store on Michigan Avenue toting housewares and home furnishings. Niketown (669 N Michigan Ave) is a five-story sports store that not only sells shoes, but includes a museum, video theater, and a display of athletic gear worn by Chicago Bulls legend Michael Jordan.
At Water Tower Place (835 N Michigan Ave), you'll find a wide range of men's and women's clothing as stores such as Lord & Taylor, Victoria's Secret, Lacoste, and French Connection.
Chicago Place (700 N Michigan Ave) is an eight-story vertical mall with more than 45 stores, including Ann Taylor Petites, Talbots, Abby & Yanni Fine Furs, and Tall Girl, and seven restaurants, including Little Tokoyo Express and Chicago Dog & Grill.
Chinatown (Cermak Road and Wentworth Ave) features more than 20 gift shops, herbal and tea stores, bakeries and 40 restaurants in its 11-block radius. Chinatown Bazaar (2221 S Wentworth) sells oriental gifts, fashion, jewelry, and antiques, and Oriental Art Imports Ltd (2239 S Wentworth) houses bone carvings, teapots, crystal, ceramics, and European canvases.
Bustling Navy Pier (600 E Grand Ave) is a good place to pick up souvenirs, including Chicago Police Department and Fire Department-themed hats and T-shirts, gourmet snacks and the usual postcards, magnets, and coffee mugs. You'll also find Sitara, which sells Indian-style clothing and handmade crafts from Bali, and TransPIERency, where you can buy stained-glass items like windows and key chains.
If you're looking for entertainment in Chicago, you'll easily find something to do. The choices are varied, ranging from the great blues clubs, the famous Second City comedy troupe, and the family-friendly ESPN Zone. Keep reading to learn more about Chicago's entertainment and nightlife.