The whirlwind milling (WM) technology is a competitive machining method, especially for large screws. A rotating large screw subjected to a rotating and moving WM cutting force has complex dynamics and formation. In the study, the WM cutting forces in radial, tangential, and axial directions were firstly acquired using a self-developed testing system. Then, the cutting vibration was modeled in consideration of the WM unique constraint, and the deflections in different directions were analyzed in detail. Lastly, the surface topography and roughness under cutting were geometrically modeled by superimposing the radial deflection on the static forming surface. Compared to single-factor experiments, the results demonstrated the consistency between surface roughness and experimental data. Therefore, the established vibration and surface roughness models are reasonable and effective for predicting, and thus favorable and beneficial for the optimization in whirlwind milling a large screw.