The first part of this thesis is devoted to the general problem of stochastic shortest path problem. It is about searching for the shortest path in a graph in which arc lengths are uncertain and specified by continuous random variables. This problem is at the core of various applications, especially in robust transportation planning where paths correspond to aircraft, train, or bus rotations, crew duties or rosters, etc. We propose a novel solution method based on a discretisation of random variables which is applicable to any class of continuous random variables. We also give bounds on the approximation error of the discretised path lengths compared to the continuous path lengths. In addition, we provide theoretical results for the computational complexity of this method. In the second part we apply this method to a real world airline transportation problem: the so-called tail assignment problem. The goal of the tail assignment problem is to construct aircraft rotations, routes consisting of flight segments, for a set of individual aircraft in order to cover a set of flight segments (legs) while considering operational constraints of each individual aircraft as well as short- to long-term individual maintenance requirements. We state a stochastic programming formulation of this problem and we show how to solve it efficiently by using our method within a column generation framework. We show the gain of our stochastic approach in comparison to standard KPI in terms of less propagated delay and thus less operational costs without growth of computational complexity. A key point of our complex approach to robust optimisation problem is the fit of the underlying stochastic model with reality. We propose a delay propagation model that is realistic, not overfitted, and can therefore be used for forecasting purposes. We benchmark our results using extensive simulation. We show a significant decrease of arrival delays and thus monetary savings on average as well as in the majority of our disruption scenarios. We confirm these benefits in even more life-like benchmarks as simulation where recovery actions are taken and in scenarios which use historical delays directly instead of the stochastic model.