Flood, as a hydrological phenomenon caused by a significant surge in the runoff water that overwhelms and overflows a drain, river, or stream, usually after heavy rainfall, tropical storms, and cyclones, has various impacts on Caribbean islands. Its adverse impacts include loss of human and domestic life, deteriorating public health, and damages to properties, and croplands. The Caribbean island of Jamaica is located in the geographical area where the current and forecasted hydrological, physical, climatic, and human conditions are set for probable flood hazard occurrences. Therefore, this study aimed at estimating the likelihood of flood hazard occurrences, and associated risk for Saint James Parish, Jamaica, and its port city of Montego Bay. It deployed a rather simple but robust method involving the Geographic Information Systems (GIS)-based Analytical Hierarchy Process (AHP) of multicriteria analysis. The AHP enlisted, prioritized (ranked), and weighed the criteria (i.e., land cover, soil, drainage density, elevation, slope, rainfall, land use, and population data) and integrated with the Weighted Sum Model (WSM) to arrive at the estimation. Accordingly, 36% of the study area is assessed to experience a very high and high probability of flood hazard occurrences. On the other hand, 25% of the study area is subjected to risks of high and very high exposure and vulnerability to the hazard. Wetlands are the most adversely impacted land-use and landcover types (i.e., 100%) followed by Builtup areas (i.e., 74%) and agricultural croplands (24%), indicating the unique vulnerability of the area to the hazards, and damages thereof. The GIS-based Multicriteria Analysis of flood risk factors of Montego Bay and surrounding areas revealed varying likelihoods of flood hazard occurrences, exposure, and vulnerability warrants policy-making attention. The expansion of public education on flood hazard areas-that is, areas where there is a 1 percent chance of a flood occurring in any given year (a 100year flood)-efficiency in response time, knowledge of flood control regulations, planning, and preparedness-is also advised in-order-to enforce citizens' environmental responsibilities.