Effective waste management is critical to environmental sustainability and public health. Various dynamics, such as seasonal changes and waste education programs, influence solid waste generation, increasing the complexity of prediction. This is important, as the proper prediction of waste quantity is necessary to develop a sustainable waste management system. In this study, municipal solid waste (MSW) management is examined in Regina, the capital city of Saskatchewan, Canada. A system dynamics (SD) model is developed to evaluate garbage and recyclable waste generation behaviours in Regina across four seasons. Three years of Regina landfill waste generation records (2016–2018) are considered to analyze and predict seasonal waste-generation trends. The effect of various factors, such as gross domestic product (GDP), population, and education attainment on the amount of waste generation is considered in the SD model. The SD model is designed as a stock-flow diagram to illustrate the relationships between variables and predict the next three years of waste trends. This finding highlights the importance of waste education and awareness program and seasonal effects on the accuracy of SD waste modeling.