The current Air Traffic Management (ATM) system worldwide has reached its limits in terms of predictability, efficiency and cost effectiveness. Different initiatives worldwide propose trajectory-oriented transformations that require high fidelity aircraft trajectory planning and prediction capabilities, supporting the trajectory life cycle at all stages efficiently. Recently proposed data-driven trajectory prediction approaches provide promising results. In this paper we approach the data-driven trajectory prediction problem as an imitation learning task, where we aim to imitate experts "shaping" the trajectory. Towards this goal we present a comprehensive framework comprising the Generative Adversarial Imitation Learning state of the art method, in a pipeline with trajectory clustering and classification methods. This approach, compared to other approaches, can provide accurate predictions for the whole trajectory (i.e. with a prediction horizon until reaching the destination) both at the pre-tactical (i.e. starting at the departure airport at a specific time instant) and at the tactical (i.e. from any state while flying) stages, compared to state of the art approaches.