Only 16 days after Jackson was released by the Royals, the Chicago White Sox offered him a three-year deal, guaranteeing $700,000 per season with a performance-based upside of $8.15 million over the term. White Sox co-owner Jerry Reinsdorf stated they did not anticipate him to play all seasons while he addressed his hip issues and avascular necrosis. Jackson played two seasons appearing in 23 games in 1991 and 85 games in 1993. He appeared on White Sox' disabled roster during the 1992 season due to completing hip replacement surgery earlier that year. It was with the White Sox that he made his only post-season appearance, in the 1993 American League Championship Series, which Chicago lost to the Toronto Blue Jays in six games.