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One of the best things about shopping in Chicago is the diversity and support for independent shops within neighborhood communities. Sure, the shopping along the Magnificent Mile and Water Tower Place is pretty sweet but if you want to get a real taste of what Chicago offers, step away from Michigan Avenue and hit up the neighborhoods.
For high-end designers like Tod’s and Prada, head towards tony Oak Street, literally steps away from Michigan Avenue. Just a touch west is River North where warehouses have been transformed into art galleries within walking distance of one another.
State Street, also known as That Great Street, is home to Macy’s and several discount chains such a Nordstrom Rack, Old Navy and DSW Shoe Warehouse. Just one block east of the southern end of State Street is Wabash Avenue, home of Jewelers Row.
Independent designers can be found at boutiques that line Division Street in Wicker Park and some outlets within neighboring Bucktown. A host of great indies can be found in family friendly outposts in Andersonville and Roscoe Village as well.
A giant designer outlet mall is in suburban Rosemont, next to O'Hare, and one of the largest indoor malls in the country, Woodfield Mall, is a little further northwest in suburban Schaumburg.
For fun and inexpensive shopping for little tchotkes, try looking in the bins at Chinatown.