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Swap trailer transport organisation problem originates from the traditional vehicle routing problem (VRP). Most of the studies on the problems assume that the travelling times of vehicles are fixed values. In this paper, the uncertainties of driving times are considered and a chance constrained programming problem is proposed. An improved simulated annealing algorithm is used to solve the problem proposed. The model and algorithm described in this paper are studied through a case study, and the influence of uncertainty on the results is analysed. The conclusion of this study provides theoretical support for the practice of trailer pickup transport.