Where to Find the Best Shopping in Chicago

Shopping in Chicago has been a popular pastime dating way back to the frontier days, when hometown brands Sears and Montgomery Ward began sending their catalog items into Americans’ homes. Marshall Field’s, opened in 1852, gave the city a pioneering department store.

The Best Shopping in Chicago

Today you can buy in the Windy City pretty much what you can buy in other American cities—well, maybe there are more Bears T-shirts here! Shoppers are drawn by the name brands conveniently consolidated on the Magnificent Mile, where you can find everything from Patagonia to Hugo Boss. Housewares and clothes are the big sellers. A favorite souvenir is the delectable Frango mint chocolates on sale at Macy’s (previously Marshall Field’s). Chicago also has an emerging local fashion scene that’s worth a look. Read on to learn where to shop in Chicago.

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Magnificent Mile

The Magnificent Mile, which runs along North Michigan Avenue from the Chicago River to Oak Street, offers hundreds of designer retail stores, shops and boutiques; it’s nirvana for anyone interested in shopping in Chicago. Here you’ll find the very best in department stores: Nordstrom, Saks Fifth Avenue, and Bloomingdale’s. A must-do stop is the original Marshall Field’s (now Macy’s), a Chicago shopping icon that opened here in 1852 and boasts century-old clocks and a Tiffany dome. Magnificent Mile stores include a Nike store, American Girl Place, and much, much more (name a popular retail brand and it’s probably on the Mile).

Oak Street

Fashionistas with expensive tastes will want to check out Oak Street, the place for haute designs from Paris, Milan, and New York. Here you’ll find some of the best boutiques in Chicago.

Bucktown and Wicker Park

The hubs of the Chicago-designed fashion scene are Bucktown and Wicker Park. These artsy side-by-side neighborhoods offer a range of boutiques from ready-to-wear to couture, as well as home decor shops (contemporary and antique), art galleries, and artist studios.

Lincoln Park

Upscale Lincoln Park has a mix of chain stores and independent boutiques offering everything from jewelry and women’s clothing to bicycles and vintage furniture.

Maxwell Street Market

Maxwell Street Market is an open-air market on South Desplaines Street, open from 7:00 a.m. to 3:00 p.m. every Sunday of the year. This is a perfect place to take a stroll and meet some of the locals. Browse past the stalls of fresh fruit, vegetables, and candies, and shop at the tables full of items for sale. Bring cash; you never know what you might find! You can also have an authentic Mexican meal here. Try steak, chicken or pork tacos, or tamales.

Garrett’s Popcorn

Looking for a local specialty food to bring home for friends and familiy? Stop by one of the many Garrett’s Popcorn locations around town. Garrett has been making fresh gourmet popcorn since it opened in the Windy City in 1949. Oprah Winfrey once called it “the best popcorn on the planet.”

Gurnee Mills

Gurnee Mills contains a mix of discount outlets and full-price stores, located less than an hour north of Chicago. Brands include American Eagle, Express Factory Outlet, Guess Factory Store, and Macy’s. There are so many stores that you could easily spend a whole day here.

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• Chicago Travel Guide
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• 10 Best Cheap Hotels in Chicago
• 9 Stylish Boutique Hotels in Chicago
• 10 Best Things to Do in Chicago
• 9 Must-See Chicago Attractions
• 10 Best Day Trips from Chicago
• Chicago with Kids: 9 Fun Family-Friendly Activities
• 10 Best Cheap Eats in Chicago
• 10 Best Places for Chicago Deep-Dish Pizza
• 10 Best Restaurants in Chicago
• What to Wear in Chicago
• What to Pack for Chicago

—Original reporting by Fran Golden