Aluminum alloys are widely used in several applications. Cast alloys are usually considered to be brittle materials leading to short chip formation during machining. Although they can be produced near net shapes, products made of these alloys very often require some machining. The purpose of this study is to evaluate the machinability of A319 and A356 under T0 and T6 conditions. The machinability was assessed during the dry drilling machining process, with the machinability indexes including the chip form, chip breakability, and the cutting forces. It was found that A319 and A356 exhibit different machinability behaviors, especially under the T6-condition in terms of force requirements, chip breakability, and chip segmentation. The chip grain size obtained by X-ray diffraction techniques was also studied and correlated to the machining conditions. It was also found that both the microstructure of the workpiece materials and the machining conditions significantly affect the chip formation mechanism, and so the machining parameters could therefore be selected to promote a chip form that is easily manageable in production.