Dry machining is one of the main ways to reduce the environmental burden of the machining process and reduce the negative effect of the cutting fluid and aerosols on operators. In addition, dry machining can reduce overall machining costs and, in the case of large workpieces, reduce the extra work associated with removing residual cutting fluid from the workpiece and adjacent area. For high-strength structural steel products, it is typical to drill holes with larger diameters of around 20 mm. Therefore, this work is devoted to the investigation of the dry drilling process carried out on a workpiece made of S960QL steel with a helical drill with a diameter of 21 mm. The aim was to find suitable cutting conditions for dry drilling with regard to process stability and workpiece quality. An experiment performed with a coolant served as a comparison base. A dry drilling experiment was performed with cutting speeds from 30 to 70 m·min⁻¹ and feeds from 0.1 to 0.3 mm·rev⁻¹, and with the results of this experiment, the same experiment with flood cooling was performed. During the drilling process, spindle torque values were recorded using the indirect spindle current recording method. The macroscopic chip morphology was studied to understand the cutting process. The chip thickness ratio was measured, as well as the maximum diameter of spiral chips. On the final workpiece, the qualitative and dimensional parameters of the holes were evaluated, such as the diameter, cylindricity and surface roughness, depending on the change in the cutting conditions and cutting environment. Evaluation of the obtained data led to the following conclusions. When drilling the S960QL material, there is only a very small increase in the drilling torque during dry drilling compared to drilling with cutting fluid. The increase in friction demonstrated by the chip thickness coefficient is significant. The influence of the environment on the dimensional accuracy showed a tendency for a slight increase in the holes’ diameters during dry machining. In comparison, the cylindricity of the dry-drilled holes shows a lower deviation than the holes drilled with cutting fluid. The surface roughness of the holes after dry drilling is affected by the increased friction of the outgoing chips, despite the resulting parameters being very good due to the drilling technology standards. This work provides a comprehensive view of the dry drilling process under defined conditions, and the results represent suitable cutting conditions to achieve a stable cutting process and a suitable quality of drilled holes.