The Project Delivery System (PDS) selection is critical for the performance of construction projects because it directly influences costs, efficiency, and stakeholder satisfaction. Despite its importance, the proper PDS selection currently disregards identifying the most relevant contractual factors and their relationship with value generation. This study compares the characteristics and behavior of various PDS to address this issue. This paper uses a comparative literature analysis of four PDS models, i.e., Design Bid Build (DBB), Design-Build (DB), Construction Management at Risk (CM), and Integrated Project Delivery (IPD), to evaluate their contractual factors and performance. The literature evidences that IPD may outperform the other models, and despite the type of PDS deployed, the most frequently used contractual factors are cost, time, communication, quality, and change. It is concluded that fostering the use of collaboration and integration processes in the structure of the PDS drives performance improvement and, hence, value generation. Further research must consider analyzing the effect of emerging factors such as sustainability and digitalization.