
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.
Armitage Avenue Ancient Victorian homes tower over the haute boutiques, pricey gift shops, and high-end chocolatiers lining this bucolic avenue. Armitage Ave.; www.armitageshopping.com
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.; 312-222-1467; www.jazzmart.com
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.; www.oakstreetchicago.com
Quimby's 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.; 773-342-0910; www.quimbys.com
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
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.; www.unclefunchicago.com
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.; 312-440-3166; www.shopwatertower.com