Drilling is widely used in manufacturing of products which need holes, for example for fluid channels, screws or pins. Depending on application, workpiece material, cutting parameters and economic considerations, different types of drills are employed. Indexable insert drills are types of drills which facilitate inserts to make holes. These types of drills can make high pitch noises due to vibrations. The focus of this thesis is to investigate the mechanism behind these vibrations in order to help reducing the generated noise in the future designs. Primary investigations show that the main mechanism which results the mentioned noise is regenerative chatter vibrations due to axial and torsional flexibilities. There is a gap in modeling of chatter vibrations in indexable drills where loadings and geometries are asymmetrical and due to torsional vibrations, delay terms are variable. The first step of simulating regenerative chatter vibrations in the drill is to model static cutting forces in a reliable way. In this thesis, a model is proposed which is capable of predicting static cutting forces through segmentation of cutting edges. Since, using this model, forces can be calculated separately on each insert, it is possible to consider differences of inserts in estimationof the cutting loads. The obtained loads are used in the chatter simulation.A model is proposed to simulate chatter vibrations by considering axialand angular deflections and the coupling between them. The resulted model isa system of delay differential equations with variable delays. Variations in timedelays, tool jump-outs and backward motions of inserts have been included inthe proposed time-domain simulation. A set of experiments is conducted toverify the model.