The software implements an application for the simulation of a smart and proactive carpooling service, based on the so called "ICON loop", an iterative architecture that mixes constraint programming and data mining/machine learning which was developed within the ICON EU project. The software autonomously infers the mobility demand of the users through the analysis of their mobility traces (i.e. Data Mining of GPS trajectories) and builds the network of all possible ride sharing opportunities among the users. Then, the maximal set of carpooling matches that satisfy some standard requirements (maximal capacity of vehicles, etc.) is computed through Constraint Programming models, and the resulting matches are proactively proposed to the users. Finally, in order to maximize the expected impact of the service, the probability that each carpooling match is accepted by the users involved is inferred through Machine Learning mechanisms and put in the CP model. The whole process is reiterated at regular intervals, thus forming an instance of the general ICON loop.