Total transfer capacity (TTC) is an index used to provide the system operators with key information necessary for the transmission network security and energy trading management. In contrast to deterministic methods, probabilistic methods are justified since they can effectively deal with the uncertainty associated with the system parameters and conditions. In addition, they are also able to cope with wind power generation which has uncertain and fluctuating power output characteristics. In this paper, the TTC is computed using Monte Carlo simulation with transient stability consideration. To alleviate the computational burden due to the addition of the transient stability constraint, decision tree classification is used as a prediction tool for the transient stability assessment during the TTC evaluation. The effectiveness of the proposed method is demonstrated through a numerical example conducted on the modified IEEE 30-bus test system integrated with wind power.