Transmission planning is an important part of power system planning to meet an increasing demand for electricity. The objective of transmission expansion is to minimize operational and construction costs subject to system constraints. There is inherent uncertainty in transmission planning due to errors in forecasted demand and fuel costs. Therefore, transmission planning process is not reliable if the uncertainty is not taken into account. The paper presents a systematic method to find the optimal location and amount of transmission expansion using Cross-Entropy (CE) incorporating uncertainties about future power system conditions. Numerical results are presented to demonstrate the performance of the proposed method.