This dissertation concerns power system expansion planning under different market mechanisms. The thesis follows a three paper format, in which each paper emphasizes a different perspective. The first paper investigates the impact of market uncertainties on a long term centralized generation expansion planning problem. The problem is modeled as a two-stage stochastic program with uncertain fuel prices and demands, which are represented as probabilistic scenario paths in a multi-period tree. Two measurements, expected cost (EC) and Conditional Value-at-Risk (CVaR), are used to minimize, respectively, the total expected cost among scenarios and the risk of incurring high costs in unfavorable scenarios. We sample paths from the scenario tree to reduce the problem scale and determine the sufficient number of scenarios by computing confidence intervals on the objective values. The second paper studies an integrated electricity supply system including generation, transmission and fuel transportation with a restructured wholesale electricity market. This integrated system expansion problem is modeled as a bi-level program in which a centralized system expansion decision is made in the upper level and the operational decisions of multiple market participants are made in the lower level. The difficulty of solving a bi-level programming problem to global optimality is discussed and three problem relaxations obtained by reformulation are explored. The third paper solves a more realistic market-based generation and transmission expansion problem. It focuses on interactions among a centralized transmission expansion decision and decentralized generation expansion decisions. It allows each generator to make its own strategic investment and operational decisions both in response to a transmission expansion decision and in anticipation of a market price settled by an Independent System Operator (ISO) market clearing problem. The model poses a complicated tri-level structure including an equilibrium problem with equilibrium constraints (EPEC) sub-problem. A hybrid iterative algorithm is proposed to solve the problem efficiently and reliably.