Regenerative chatter vibrations are common in drilling processes. These unwanted vibrations lead to considerable noise levels, damage the quality of the workpiece, and reduce tool life. The aim of this study is to simulate torsional and axial chatter vibrations as they play important roles in dynamic behavior of indexable insert drills with helical chip flutes. While asymmetric indexable drills are not the focal points in most of previous researches, this paper proposes a simulation routine which is adapted for indexable drills. Based on the theory of regenerative chatter vibration, a model is developed to include the asymmetric geometries and loadings that are inherent in the design of many indexable insert drills. Most indexable insert drills have two inserts located at different radial distances, namely central and peripheral inserts. Since the positions of the central and peripheral inserts are different, the displacement and thereby the change in chip thickness differs between the inserts. Additionally, the inserts have different geometries and cutting conditions, e.g., rake angle, coating, and cutting speed, which result in different cutting forces. This paper presents a time-domain simulation of torsional and axial vibrations by considering the differences in dynamics, cutting conditions, and cutting resistance for the central and peripheral inserts on the drill. The time-domain approach is chosen to be able to include nonlinearities in the model arising from the inserts jumping out of cut, multiple delays, backward motions of edges, and variable time delays in the system. The model is used to simulate cutting forces produced by each insert and responses of the system, in the form of displacements, to these forces. It is shown that displacements induced by dynamic torques are larger than those induced by dynamic axial forces. Finally, the vibration of a measurement point is simulated which is favorably comparable to the measurement results.