• Jackson Park Highlands District
• South Shore Cultural Center (former South Shore Country Club)
• Allan Miller House
• Jackson Park

South Shore takes its name from its position along the city's southern lakefront, developing out of a scattering of smaller settlements — Essex, Bryn Mawr, Parkside, Cheltenham Beach, and Windsor Park — within Hyde Park Township before annexation to Chicago in 1889. The World's Columbian Exposition, held nearby in Jackson Park in 1893, spurred the sale of land and building lots, and the neighborhood's population exploded from roughly 32,000 in 1920 to nearly 79,000 by 1930.

At the neighborhood's northern edge sits Jackson Park Highlands, designated a Chicago Landmark in 1989 for its exceptional collection of American Foursquare, Colonial Revival, and Renaissance Revival homes built starting in 1905. The former South Shore Country Club, purchased by the Chicago Park District in 1972, now serves as the South Shore Cultural Center, one of the community's enduring civic anchors.

For anyone who has walked the Highlands' suburban-sized lots or strolled the grounds of the old Country Club, MY-NHD's South Shore tee is a way to carry that lakefront history with you.