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No matter the limit of your wallet, Chicago boasts a seemingly limitless array of shopping opportunities, from exclusive boutiques and urbane department stores to multi-level shopping malls and funky streetside shops. Best of all for die-hard hunters and gatherers, the city's premier shopping venues are centrally located and can easily be covered on foot. No wonder it's called the "City of Big Shoulders" – the bigger the shoulders, the more shopping bags you can carry! Keep in mind that Chicago sales tax is 9% on most purchases.

Shopping in Chicago

Armitage Avenue

Ancient Victorian homes tower over the haute boutiques, pricey gift shops, and high-end chocolatiers lining this bucolic avenue.

Armitage Ave., IL,
Tags: shopping | expensive | editor pick | designer

Jazz Record Mart

It’s no surprise that a city synonymous with live music, also houses the largest jazz and blues record store in the world.

27 E. Illinois St., IL, 312-222-1467,
Tags: shopping | moderate | trendy | vintage | records

Oak Street

If Chicago has a Fifth Avenue or a Rodeo Drive, this is it. Hermes, Prada and Barneys New York are just a few of the big name retailers.

Oak St., IL,
Tags: shopping | expensive | designer


It’s just your average neighborhood anarchist bookstore. Underground ‘zines, vintage erotica, indie comics, and local authors are all well represented.

1854 W. North Ave., IL, 773-342-0910,
Tags: shopping | moderate | trendy | books

Southport Corridor

This former desolate stretch of no man's land has benefited well from overnight gentrification. It’s now one of the hottest boutique enclaves in town.

Southport Corridor, IL,
Tags: shopping | moderate | trendy | designer

The Magnificent Mile

Although most famous for its retail offerings, the so-called Magnificent Mile mixes splashy shops like Niketown, American Girl Place, and the Apple Store with architectural landmarks like the Tribune Tower, a 40-story neo-gothic skyscraper speckled with pieces of the pyramids at Cairo; Westminster Abbey; and other famed sites representing all 50 states and dozens of nations. Conclude the shopping trail at Water Tower Place, a vertical mall with more than 100 stores and striking glass elevators. Or, explore the Historic Water Tower building, located one block south of the mall on Michigan Avenue; the limestone, castle-like structure is one of the few to survive the Great Chicago Fire of 1871, and admission is free.

North Michigan Avenue, from the Chicago River to Lakeshore Drive, IL,
Tags: shopping | things to do | architecture

Uncle Fun

You could spend a day inside this tiny storefront and still not unearth all the novelty items, vintage treasures, and pop culture memorabilia on display.

1338 W. Belmont Ave., IL,
Tags: shopping | moderate | novelty

Water Tower Place

Macy’s is the anchor store at this vertical shopping mall that features 70 stores and beautiful glass elevators.

835 N. Michigan Ave., IL, 312-440-3166,
Tags: family | shopping | moderate | shopping mall

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