MAGNIFICENT MILE. This shopping center features more than 450,000 square feet of space and includes many name-brand stores like Bloomingdale's, Gucci, Williams-Sonoma Grande Cuisine, and J. Crew. The complex also includes dining options that range from casual to sophisticated. Baisi Thai, Oak Tree, and Seasons Restaurant (of the adjacent Four Seasons Hotel) can all be found here. N.B. Some stores may be open extended hours.

Oakbrook Center sits just 30 minutes from downtown Chicago and features major department stores and over 160 shops and restaurants. The open-air mall features lovely gardens and fountains, and all your favorite stores are here, including Neiman Marcus, Sears, Bloomingdale's, Macy's, and Nordstrom. You'll also find specialty stores like Crate & Barrel, Kenneth Cole, and J. Jill.

OLD TOWN. Piper's Alley is an interesting mix of theatre, dining, nightlife, and shopping options. This smartly renovated building features exposed brick walls and lively colors and six floors of entertainment choices. Browse the stores, eat at the notable Adobo Grill, sip on a martini at the Tequila bar, or catch a show at the Loews Movie Theatre, the Black Orchid performance theatre, or the Second City comedy club.

STREETERVILLE. River East Plaza is a venture at a historic site located on the North Pier. The 500,000-square-foot building hosts a number of art galleries, along with office space. If you get hungry or thirsty, visit Fox & Obel Food Market or Dick's Last Resort. A fine wines shop is also available.

RIVER NORTH. The Merchandise Mart is the largest wholesale design center as well as the world's largest commercial building. Sixty percent of the building is used for wholesale showrooms alone. The facility features over 4.2 million square feet, covers two city blocks, and stands 25 stories. Over 50 retail stores and restaurants are located here as well as showroom floors that represent the commercial, residential, kitchen and bath, decorative accessories, and gift industries. A 90-minute walking tour of the mart is available.