The Near South Side is a community area of Chicago, Illinois, United States, just south of the downtown central business district, the Loop. The Near South Side's boundaries are as follows: North—Roosevelt Road ; South—26th Street; West—Chicago River between Roosevelt and 18th Street, Clark Street between 18th Street and Cermak Road, Federal …The Near South Side is a community area of Chicago, Illinois, United States, just south of the downtown central business district, the Loop. The Near South Side's boundaries are as follows: North—Roosevelt Road ; South—26th Street; West—Chicago River between Roosevelt and 18th Street, Clark Street between 18th Street and Cermak Road, Federal between Cermak Road and the Stevenson Expressway just south of 25th Street, and Clark Street again between the Stevenson and 26th Street; and East—Lake Michigan.