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Best Outdoor Shopping in Chicago

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The Magnificent Mile
North Michigan Avenue Chicago, IL 60611
(312) 642-3570
Chicago’s Magnificent Mile area, featuring four shopping centers, world-renowned boutiques, and locally acclaimed designers, is a shopper’s paradise. Running along north Michigan Avenue from the Chicago River to Oak Street, the Magnificent Mile features department stores such as Bloomingdale’s, Lord & Taylor and Nordstrom, home furnishing retailers such as Crate & Barrel and Pottery Barn, jewelers such as Tiffany and Van Cleef & Arpels, big name apparel retailers such as Gap, Banana Republic and Ralph Lauren, as well as a host of boutiques and specialty shops. If shopping makes you hungry stop at one of the many outdoor cafes or enjoy the ambiance of ethnic or American style restaurants. And if you’re looking to get inspired take in one of the cultural experiences including an outstanding theater, classic or on-the-edge comedy, inspirational music, modern sculpture, and celebrated works of art.
Oak Street
East Oak Street Chicago, IL 60611
1-888-909-550
The destination of shoppers from all over the world, Oak Street is an International style center, housing many of the world's most exclusive boutiques and salons in addition to world-famous designer stores, such as Jimmy Choo, Prada, and Vera Wang. Nowhere will you find better selections and service. Oak Street’s assortment of prestigious stores offer unique and upscale clothing, shoes, jewelry, home furnishings, art, linens, and music. Pamper yourself at one of the full spa facilities, salons or yoga classes. You will also find magnificent restaurants, premier hotels, movie theaters, banking, and valet parking so it’s truly a one-stop shop!
Lincoln Park
Armitage Avenue, Halsted Street, and Webster Avenue Chicago, IL 60614
Fabulous boutiques, restaurants, and salons adorn the streets of one of Chicago’s most desirable neighborhoods, Lincoln Park. As you stroll down the sidewalks while shopping, enjoy the scenic atmosphere of tree-lined streets and Victorian row houses. You will find furniture, clothing, antiques, jewelry, home accessories, tabletops, and shoes in an array of intimate and sophisticated shops. Some of the boutiques in the area include Art Effect, Cotelac, Cynthia Rowley, B Boutique, and Mint Julep. Round out your outing with a stop at one of the many four-star restaurants, hair salons or spas. The website provides a list of philanthropic, art, fashion, and social happenings in the area.
Bucktown/Wicker Park
Division St., Damen Ave., Milwaukee Ave. and North Ave. Chicago, IL 60622
Bucktown/Wicker Park is slowly becoming the nucleus of fashion for many Chicago trendsetters. With boutiques like Akira, Marc by Marc Jacobs, Scoop NYC, P.45, Stitch, Cynthia Rowley and BCBG, there is a 100% chance that you will find something fab to wear to the next big Sneaky Sunday party. The shopping selection in this area is as diverse and colorful as the people who live there.
Southport Avenue
3200-4000 Southport Ave Chicago, IL 60657-3204
Southport Avenue has been established as one of the hottest neighborhoods in northern Chicago. The area appeals to upscale, urban families with its mix of restaurants, clothing boutiques, and cafes. Tree-lined side streets and renovated historic homes provide a scenic background to your shopping excursion. Boutiques like Krista K and Red Head Boutique attract the young and fashionable with its availability of hot new designers that aren’t widely available in Chicago. On the other hand, Shane offers more casual clothing for both sexes. Other boutiques include Ciao Bella, Freesia, Trousseau, Xksito, M 2, and Tula. While in the neighborhood, visit Schubas Tavern, the historical Music Box Theatre, and the Mercury Theater.
Chicago Premium Outlets
1650 Premium Outlets Boulevard Aurora, IL 60502
(630) 585-2200
Enjoy an unparalleled collection of 120 designer and name brand stores offering savings of 25% to 65% every day at Chicago Premium Outlets, located about 40 miles west of Chicago. Amidst the outdoor village setting and covered galleries, you will find Polo Ralph Lauren, Giorgio Armani, MaxMara, Kate Spade, Calvin Klein, Coach, Villeroy and Boch, Jones New York, Diesel, Dooney and Bourke, Salvatore Ferragamo, Nike, Waterford Wedgwood and more. Check out the newest addition to Chicagoland’s bargain gems, Elie Tahari, to satisfy the materialist in you. If you work up an appetite during your bargain hunting, have no fear: Chicago Premium Outlets has multiple restaurants, cafes, and dessert options to satisfy your hunger. Hours of Operation: Mon-Sat 10am-9pm; Sun 10am-6pm
Westfield Old Orchard
4999 Old Orchard Skokie, IL 60077
847-674-7070
Located just north of Chicago in Skokie, Westfield Old Orchard has been a favorite shopping destination in metropolitan Chicago since its opening in 1956. Take a stroll through the center’s garden-like atmosphere while shopping at over 150 upscale, designer stores and top-of-the-line department store anchors Bloomingdales, Macy's, Nordstrom, and Lord & Taylor. The open-air shopping center features inviting places to sit, endless fine eateries, children’s play area, and a water garden so you can relax your swiping hand. When you are finished shopping, you escape reality and catch a movie at one of Old Orchard’s two cinemas.
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