Background: Prolonged length of stay (LOS) after a hip fracture is associated with increased mortality. Purpose: We sought to create a model to predict prolonged LOS in elderly Chilean patients with hip fractures managed during the COVID-19 pandemic. Methods: Employing an official database, we created an artificial neural network (ANN), a computational model corresponding to a subset of machine learning, to predict prolonged LOS (≥14 days) among 2686 hip fracture patients managed in 43 Chilean public hospitals during 2020. We identified 18 clinically relevant variables as potential predictors; 80% of the sample was used to train the ANN and 20% was used to test it. The performance of the ANN was evaluated via measuring its discrimination power through the area under the curve of the receiver operating characteristic curve (AUC-ROC). Results: Of the 2686 patients, 820 (30.2%) had prolonged LOS. In the training sample (2,125 cases), the ANN correctly classified 1,532 cases (72.09%; AUC-ROC: 0.745). In the test sample (561 cases), the ANN correctly classified 401 cases (71.48%; AUC-ROC: 0.742). The most relevant variables to predict prolonged LOS were the patient’s admitting hospital (relative importance [RI]: 0.11), the patient’s geographical health service providing health care (RI: 0.11), and the patient’s surgery being conducted within 2 days of admission (RI: 0.10). Conclusions: Using national-level big data, we developed an ANN that predicted with fair accuracy prolonged LOS in elderly Chilean patients with hip fractures during the COVID-19 pandemic. The main predictors of a prolonged LOS were unrelated to the patient’s individual health and concerned administrative and organizational factors.