• Jackson Park Golf Course
• Jackson Park (1893 World's Columbian Exposition site)
• Chicago Landmark designation (1989)
• Metra Electric District tracks

Jackson Park Highlands takes its name from a ridge that once overlooked a lagoon in neighboring Jackson Park, the 500-acre South Side park that hosted the 1893 World's Columbian Exposition. Chicago alderman and real estate developer Frank Ira Bennett, working with Charles Bour, laid out the 80-acre subdivision in 1905 as a collection of model homes designed to overlook the prized parkland less than a decade after the World's Fair had put it on the map.

The Highlands set the standard for the era's most progressive subdivision planning: fifty-foot-wide lots, thirty-foot building setbacks, underground utilities, and no alleys, with every house required to be faced in brick or stone. Most early residents relocated from the once-elegant Washington Park neighborhood, and the district, designated a Chicago Landmark in 1989, still borders the 18-hole Jackson Park Golf Course to the north and the Metra Electric District tracks to the south.

MY-NHD's Jackson Park Highlands collection is built for a neighborhood planned from its first survey stake to overlook one of the city's grandest parks, and it still does.