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There are SO many places to shop in Chicago - if you're looking for mainstream shopping, from big chains to famous department stores, be sure to check out the Magnificent Mile - a stretch of shopping on Michigan Ave.
Also check out the Lincoln Park neighborhood, where you'll find Lori's Shoes ("the sole of Chicago"), McShane's Exchange (a GREAT resale shop), and, my personal favorite, Art Effect, where you can buy plenty of really interesting gifts, accessories, clothing, housewares, and more.
Another fun neighborhood for shopping is the Bucktown/Wicker Park neighborhood - there are plenty of independent designers and shops - perfect for finding that one item that you won't see every day.
I like this site for more interesting shopping neighborhoods, etc.: http://www.conciergepreferred.com/host_cities/1-chicago/categories/2-2-shopping
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