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The Magnificent Mile, Bucktown, Lincoln Park—these are the neighborhoods you go to when you've got cash to burn, but Chicagoans don't typically venture to the South Side for a day of shopping. Although Bridgeport might be off the beaten path, don't write it off just yet. While it's not Michigan Avenue (we like it that way) and will always be known as the land of the White Sox, this neighborhood boasts a small, eclectic shopping scene that is definitely worth the trip.
RECOMMENDED: Bridgeport neighborhood guide