The August 5-8 visit by Lee Hee-Ho is ostensibly humanitarian in nature, with the 93-year-old planning to tour a children's hospital, a maternity home and an orphanage in Pyongyang.
But all eyes are on whether she will meet with North Korean leader Kim Jong-Un, who has yet to receive any South Korean citizen since formally assuming power more than three years ago.
Her late husband is best known for his "sunshine policy" of engagement with the North that led to a historic summit with Kim Jong-Il in 2000.
The policy - which helped Kim Dae-Jung win a Nobel Peace Prize in 2000 - was largely abandoned when a conservative administration took power in Seoul in 2008 and cross-border relations soured.
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A series of nuclear and missile tests, as well as occasional military clashes along the border, have kept tensions on a high simmer.
But Kim Dae-Jung still commands some level of respect from Pyongyang, and the North's pugnacious state media has refrained from subjecting him to the same personal, vitriolic attacks it reserves for most South Korean presidents, past and present.
And Lee's visit - personally approved by Kim Jong-Un - may offer a window for resuming a dialogue over relatively non-political issues, said Jeung Young-Tae, an analyst at the Seoul-based Korea Institute for National Unification.
Those might include long-stalled talks to hold another family reunion for those separated during the 1950-53 Korean War, as well as the resumption of tours to a scenic mountain resort in the North, he said.