Caesarean section (CS) rate has seen a significant increase in recent years, especially in industrialized countries. There are, in fact, several causes that justify a CS; however, evidence is emerging that non-obstetric factors may contribute to the decision. In reality, CS is not a risk-free procedure. The intra-operative, post-pregnancy risks and risks for children are just a few examples. From a cost point of view, it must be considered that CS requires longer recovery times, and women often stay hospitalized for several days. This study analyzed data from 12,360 women who underwent CS at the “San Giovanni di Dio e Ruggi D’Aragona” University Hospital between 2010 and 2020 by multiple regression algorithms, including multiple linear regression (MLR), Random Forest, Gradient Boosted Tree, XGBoost, and linear regression, classification algorithms and neural network in order to study the variation of the dependent variable (total LOS) as a function of a group of independent variables. We identify the MLR model as the most suitable because it achieves an R-value of 0.845, but the neural network had the best performance (R = 0.944 for the training set). Among the independent variables, Pre-operative LOS, Cardiovascular disease, Respiratory disorders, Hypertension, Diabetes, Haemorrhage, Multiple births, Obesity, Pre-eclampsia, Complicating previous delivery, Urinary and gynaecological disorders, and Complication during surgery were the variables that significantly influence the LOS. Among the classification algorithms, the best is Random Forest, with an accuracy as high as 77%. The simple regression model allowed us to highlight the comorbidities that most influence the total LOS and to show the parameters on which the hospital management must focus for better resource management and cost reduction.