Lung size measurements play an important role in transplantation, as optimal donor-recipient size matching is necessary to ensure the best possible outcome. Although several strategies for size matching are currently used, all have limitations, and none has proven superior. In this pilot study, we leveraged deep learning and computer vision to develop an automated system for generating standardized lung size measurements using portable chest radiographs to improve accuracy, reduce variability, and streamline donor/recipient matching. We developed a 2-step framework involving lung mask extraction from chest radiographs followed by feature point detection to generate 6 distinct lung height and width measurements, which we validated against measurements reported by 2 radiologists (T.A. and W.B.G.) for 50 lung transplant recipients. Our system demonstrated <2.5% error (<7.0 mm) with robust interrater and intrarater agreement compared with an expert radiologist review. This is especially promising given that the radiographs used in this study were purposely chosen to include images with technical challenges such as consolidations, effusions, and patient rotation. Although validation in a larger cohort is necessary, this study highlights artificial intelligence’s potential to both provide reproducible lung size assessment in real patients and enable studies on the effect of lung size matching on transplant outcomes in large data sets.