Interoperability and Integration of the Building Information Modeling (BIM) and Building Energy Modeling (BEM) tools are major challenges for the Architecture, Engineering, and Construction (AEC) industry. The goals of this dissertation were to (i) investigate various BEM tools to evaluate their workflow and integration with BIM and (ii) assess BEM tools’ accuracy in predicting/simulating whole building energy performance from a broader lens to a more specific one (i.e., EUI to end-use data, respectively). To conduct the research study, case study buildings were selected from various categories, representing different building types (i.e., academic, administrative, and recreational). The case study buildings were located on the campus of the University of Massachusetts Amherst (UMass Amherst), and the main criterion in their selection was the accessibility of their construction document and measured energy data. BEM tools from three categories of BIM-integrated, BIM-interoperable, and BIM-separated BEM tools were selected, aiming to evaluate design-analysis workflows. To comparatively analyze the simulated energy data against each other and measured data, case study buildings’ actual energy data was collected and used. The research findings suggest potential developments that are essential to accomplish a streamlined BIM to BEM workflow, making it less tedious and time-consuming.