Women with chronic medical conditions are at increased risk for pregnancy-related complications, yet little research has addressed how women with diabetes, hypertension, and obesity perceive their pregnancy-associated risks or make reproductive health decisions. Focus groups were conducted with 72 non-pregnant women stratified by chronic condition (diabetes, hypertension, obesity) and by previous live birth. Participants discussed their intention for future pregnancy, preconception health optimization, perceived risk of adverse pregnancy outcomes, and contraceptive beliefs. Four major themes were identified, with some variation across medical conditions and parity: (1) Knowledge about pregnancy risks related to chronic medical conditions was limited; (2) Pregnancy intentions were affected by diabetes and hypertension, (3) Knowledge about optimizing preconception health was limited; and (4) Lack of control over ability to avoid unintended pregnancy, including limited knowledge about how medical conditions might affect contraceptive choices. Women with diabetes and hypertension, but not obesity, were generally aware of increased risk for pregnancy complications, and often expressed less intention for future pregnancy as a result. However, diabetic and hypertensive women had little knowledge about the specific complications they were at risk for, even among those who had previously experienced pregnancy complications. Neither chronic condition nor perceived risk ensured intent to engage in preconception health promotion. We observed knowledge deficits about pregnancy-related risks in women with diabetes, hypertension, and obesity, as well as lack of intent to engage in preconception health promotion and pregnancy planning. These findings have important implications for the development of preconception care for women with chronic medical conditions.