Background During the past decades, life expectancy has continued to increase in most high-income countries. Previous research suggests that improvements in life expectancy have primarily been driven by advances at the upper end of the health distribution, while parts of the population have lagged behind. Using data from the entire Swedish population, this study aims to examine the life expectancy development among subgroups of individuals with a history of common diseases relative to that of the general population. Methods The remaining life expectancy at age 65 was estimated for each year in 1998-2017 among individuals with a history of disease, and for the total Swedish population. We defined population subgroups as individuals with a history of myocardial infarction, ischemic or hemorrhagic stroke, hip fracture, or colon, breast, or lung cancer. We further distinguished between different educational levels and Charlson comorbidity index scores. Results Life expectancy gains have been larger for men and women with a history of myocardial infarction, ischemic or hemorrhagic stroke, and colon or breast cancer than for the general population. The life expectancy gap between individuals with a history of hip fracture or lung cancer and the general population has, however, been growing. Education and comorbidity have affected mortality levels, but have not altered the rate of increase in life expectancy among individuals with disease history. The female advantage in life expectancy was less pronounced among individuals with disease history than among the general population. Conclusions Life expectancy has increased faster in many subpopulations with a history of disease than in the general population, while still remaining at lower levels. Improvements in life expectancy have been observed regardless of comorbidity or educational level. These findings suggest that the rise in overall life expectancy reflects more than just improved survival among the healthy or the delayed onset of disease.