Background: We identify representative types of simultaneous tobacco use and alcohol consumption trajectories across the life course and estimate their association with cardiovascular and chronic respiratory diseases (CVDs and CRDs) among older people in Chile. Methods: We used data from a population-representative, face-to-face and longitudinal-retrospective survey focused on people aged 65–75 (N = 802). To reconstruct trajectory types, we employed weighted multichannel sequence analysis. Then, we estimated their associations with CVDs and CRDs through weighted logistic regression models. Results: Long-term exposure to tobacco use and alcohol consumption across life are associated with the highest CVD and CRD risks. Long-term nonsmokers and nondrinkers do not necessarily show the lowest CVDs and CRDs risks if these patterns are accompanied by health risk factors such as obesity or social disadvantages such as lower educational levels. Additionally, trajectories showing regular consumption in one domain but only in specific periods of life, whether early or late, while maintaining little or no consumption across life in the other domain, lead to lower CVDs or CRDs risks than trajectories indicating permanent consumption in both domains. Conclusions: A policy approach that considers CVDs and CRDs as conditions that strongly depend on previous individual experiences in diverse life domains can contribute to the improved design and evaluation of preventive strategies of tobacco use and alcohol consumption across the life course.