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The evolution of Chicago's South Side turned an unpretentious frontier settlement on the western shores of Lake Michigan into the City of Big Shoulders. It started with scattered clusters of wild garlic whose abundance provided olfactory justification for its Indian designation: Chicagou, or “smelly place.” The pivotal geographical element of the region, beyond Lake Michigan itself, was the Chicago River, which flowed out of the Great Lake for a mile before dividing into northern and southern branches. From the Chicago River, European explorers could portage to the Des Plaines River, paddle to the Illinois River, and, eventually, reach the Mississippi. This easy access to interior hinterlands set the stage for the South Side's importance in the early days of town building.

A smattering of settlers appeared along the Chicago River by the 1790s, but real development had to wait until resolution of the Black Hawk War in 1832. Early residents favored the area south of the main branch of the Chicago River because it provided access to both Lake Michigan and the south branch. Along this stretch of the river developed landing slips and sawmills where Wisconsin timber was turned into lumber for the balloon-style housing that was so popular across the Midwest. Other businesses that made use of the slow-moving waterway included grain elevators and flour mills. Vital to the future of the South Side and to the city as a whole was completion of the Illinois and Michigan Canal in 1848. By connecting the southern branch of the Chicago River to the downstream rivers (eliminating the need for a portage), the Great Lakes now “reached” the Mississippi River through a continuous water route. Chicago's dominance as the nation's leading lake port was insured. When railroads arrived over the next decade, they typically approached Chicago through the South Side as they detoured northward off the main transportation corridor from the East Coast to the Mississippi. Rail lines brought more factories, jobs, and workers.

With the coming of the Civil War, Chicago entrepreneurs envisioned a unique opportunity to seize the nation's “porkopolis” crown from Cincinnati. Local livestock interests shrewdly drew their scattered stockyards into a centralized location on the South Side in 1865, intending to create a single railhead for the sale of the region's hogs and cattle. In turn, the Union Stockyards nurtured a second concentration of businesses. Meatpackers, whose national markets expanded rapidly following the refinement of refrigerated boxcars in the 1870s, saw the wisdom of building slaughtering plants alongside the stockyards. About the same time, George Pullman created his model industrial town on the far South Side, west of Lake Calumet. Just as the Union Stockyards spawned Packingtown, so, too, did the Town of Pullman lure other industries to the Lake Calumet area, creating a second destination for Great Lakes steamers. In 1922, the Cal-Sag Canal was built westward from Lake Calumet, providing a second link between Lake Michigan and the Mississippi River—both transecting the South Side. Also in the 1880s, a short distance from Pullman's car shops, the Illinois Steel Corporation built a manufacturing site that would eventually grow into the giant South Chicago Steel Works complex. By the beginning of the 20th century, the future of the essential Great Lakes-Mississippi River link was guaranteed when the Chicago Ship and Sanitary Canal replaced the Illinois and Michigan Canal and, in the process, addressed recurring health problems by reversing the flow of the Chicago River and emptying its pollutants into Lake Michigan. The South Side had become the focal point for the area's industrial might. A century later, however, these same industrial behemoths had corroded into stereotypical representatives of the late 20th century's Rust Belt.

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