Dry drilling of thick carbon fiber reinforced polymer (CFRP) laminates requires careful selection of process parameters in order to obtain acceptable borehole surface quality. Complex contact conditions between the drill margin and the borehole surface determine the integrity of the borehole surface depending on the process parameters and temperature-dependent viscoelastic material properties. Temperature rise during dry drilling reduces the elastic modulus of the CFRP and causes thermal expansion of the drill, resulting in considerable contact length at the drill margin and borehole surface interface. Manufacturers need a better understanding of the interaction among contact pressure, sliding velocity, temperature at the interface, and temperature-dependent material properties to develop predictive models for drilling CFRPs. To examine this complex interaction, this study develops a novel, hybrid model that combines a time-based analytical modeling of drilling process with a finite element-based modeling of temperature rise. Drilling experiments were performed in which thrust force, torque, and temperature were measured as a function of feed, and these measurements were used to identify unknown hybrid model parameters. The results revealed that a significant change in friction conditions occurs when increased temperatures at the margin and borehole surface interface approach and exceed the glass transition temperature of the CFRP laminate at a large feed rate. These findings show the benefit of increasing feed during dry drilling, which is nonetheless limited by the temperature-dependent material properties of the work material.