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This area of Chicago begins just south of the Loop and stretches south to the City Limits, generally the Calumet River. The South Side is a pretty big area, and it is a conglomeration of a great deal of neighborhoods. Redevelopment in much of this area has lingered at the doorstep, with an occasional nonprofit developer giving neighborhoods the once-over. All along, residents and developers agreed that the South Side has many of the necessary assets for revival. It is favorably located, amply convenient to downtown Chicago. Its eastern border is along beautiful Lake Michigan, and much of the shoreline beaches have recently been renovated.

Two prominent South Side neighborhoods are Bridgeport and Chinatown. Bridgeport came into being more than 160 years ago, when immigrants arrived and built the Illinois & Michigan Canal to link Lake Michigan and the Illinois River. Many arrived from Italy, Lithuania, Poland, and Ireland, hoping to recreate the tight-knit communities they had left behind. These immigrants settled in “Hardscrabble”, which was renamed “Bridgeport” in 1836, after a low bridge that crossed the South Branch of the Chicago River. Ships couldn’t fit under the bridge, and were forced to stop and unload their cargo, making the river on the lake-side of the “bridge” a “port.” When the canal was built, Bridgeport residents worked in the stockyards and packing houses of the “Back of the Yards” to the immediate south. Though it's mainly a residential area, Bridgeport is bisected by a busy central commercial district along Halsted Street. Here, Italian and Lithuanian restaurants mingle with Chinese grocers and discount variety stores. The Ramova Theater, shuttered but still displaying its marquee, is the only visible reminder of the half-dozen theaters that used to dot the neighborhood. An evening in Bridgeport is best enjoyed in one of its many taverns or restaurants. Unless, of course, there's a game at Comiskey Park (home of the Chicago White Sox), in which case follow the bright lights illuminating the sky above 35th Street near the Dan Ryan.

The sounds and smells of Chinatown are like none other in Chicago. Besides the great food of this colorful neighborhood, you'll also find unique boutiques full of imported gifts, tea shops, and any number of other interesting stopping points. The entrance to Chinatown’s oldest and most-compact section is depicted by the Chinatown Gateway; you’ll know it by the ornamental street lamps and Chinese dragon carvings on the sidewalks.

For years, the South Side has been notorious for its gangs and drug dealers, empty buildings and high crime rates. This has been an area for the poor and the disadvantaged. Problems aside, it isn’t a community without hope and it is beginning to enjoy revitalization. For instance, on the east side plans have been announced to upgrade Jackson Park and expand La Rabida Hospital. And to the south, the land formerly occupied by the South Works steel mill along the Lake is being redeveloped for industry and potentially homes. There are plenty of grand, old mansions ready for rehabbing and plenty more vacant lots aching for new houses and condos. It may take a little while, but as the highways out of the City continue to become more and more congested, its probably a safe prediction that this area will continue to see revitalization as people turn to the South Side and away from suburbia.
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