It is of vital significance to accurately forecast the settlement of high fill subgrade, which is the foundation for disaster prevention and treatment of subgrade. According to the monitoring data of high fill subgrade, a novel model, called PSOMGVM model, based on particle swarm optimization (PSO) and Markov chain is proposed. Firstly, the typical characteristics of settlement curve are analyzed from the aspect of geomechanics theory and based on the grey theory, the grey Verhulst model (GVM) with unequal time-interval is proposed. Then, according to the theory of Markov chain, the grey Verhulst model is built to revise the relative residuals of the GVM, in which the effects of volatility characteristics can be considered. Finally, the PSOMGVM model based on PSO algorithm and Markov chain is set up, which whitens the parameters of the grey interval. In order to demonstrate the fitness and the ability of the proposed model, five competing models are introduced to predict the settlement of the high fill subgrade of Xiangli Expressway in Yunnan Province. Through the analysis of APE, MAPE, and RMSE, it states that the accuracy and performance of the PSOMGVM model outperform the other five competing models for simulative and predictive periods.