In this study, tool wear and chip formation during the drilling process of AISI 1045 material using plasma-nitrided high-speed steel drill bits were experimentally investigated. Two uncoated and plasma-nitrided drill types were used in the experiments. First, commercial drill bits were subjected to the plasma nitriding process. Following this, the drilling processes were carried out at various feed rates and cutting speeds. A sensitive computer numerical control machine was used in the experiments. Tool wear was determined using scanning electron microscopy and chips obtained from the drilling process were observed under microscopy. Finally, the relationship between the chip cross section and tool wear was determined using statistical analysis. It was concluded that the mechanical properties of uncoated high-speed steel drill bits improve significantly through the plasma nitriding process. Less tool wear and a good chip formation were observed with the improvement of the mechanical properties. It was determined that there is a relationship between the chip section and wear.