Based on the tension stiffening effect, the work aims to study the influence mechanism of grinding chatter on the workpiece’s surface topography by conducting the prestress to adjust the chatter strength. The 45 steel was selected to be the research object. A two-degree grinding system’s dynamic model was established firstly. Meanwhile, the time domain method and the frequency domain method were combined to calculate the dynamic characteristic of the grinding system. Moreover, the non-Gaussian distribution of the wheel’s grits was obtained by Johnson transformation. Based on the grits’ movement trajectory and the grinding system’s dynamic characteristics, a surface topography mathematic model coupled with multi-factors was established accordingly to further obtain the workpiece’s surface topography in consideration of the grinding chatter factor. The workpiece’s microscopic surface height varied from 1.1~1.7 μm under prestress condition. Moreover, the average surface height increased along with the wheel’s feeding direction. The calculated workpiece’s surface height was closer to the measurement average data. Moreover, the workpiece’s surface height decreased with the increase of the wheel’s rotation speed, but it went up with the increase of the wheel’s feeding rate. By comparing with the workpiece’s surface height between the experiment and the simulation, it can be found that grinding chatter can lead to inconsistency of the workpiece’s surface topography distribution. The workpiece’s microscopic surface height increases along with the wheel’s feeding direction. Meanwhile, the grinding chatter can enlarge the workpiece’s surface height to a large extent. Therefore, the influential effect of grinding chatter on the workpiece’s microscopic surface height can be weakened by increasing the wheel’s rotation speed and decreasing the wheel’s feeding rate in the actual prestress grinding process.