Touring South Shore, Part 1: History and the Highlands

Our link to RedEye’s “next hot ‘hood” article generated a lot of comments, some of which touched on the present and future of the South Shore on the city’s South Side. We couldn’t think of any contacts in the area, so I called up Bob Dickinson of the Southside Builders Association, who in turn put me in touch with Jeff Heilbrunn, a marketing adviser for Builders Center of Chicago.

Heilbrunn should know South Shore — not only has he worked on several Builders Center projects in the neighborhood, but he actually spent the first 20 years of his life there. He grew up on Colfax Avenue, attended South Shore High School, played golf in Jackson Park, and spent his summer days at Rainbow Beach.

In the first video from today’s drive-around, Jeff takes me through the Jackson Park Highlands District on South Shore’s northwest side. There, you can find century-old single-family homes in a variety of architectural styles, built on 50-foot lots with generous setbacks. As we wound through these streets, Jeff described the South Shore he remembers from the ’50s and ’60s, and mentions some of the notable names who have emerged from the neighborhood.

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