Abstract: A drilling apparatus capable of removing drill chips from a workpiece under vacuum. The drilling apparatus includes an elongated drill having a body and a shank. The body has an axial through hole to receive drill chips. The shank has a plurality of radial holes communicated with the axial holes of the body. A vacuum adapter is hermetically placed around the shank and includes a cylindrical hollow body. The hollow body of the adapter includes a radial through port. The radial through port has one end communicated with the radial holes and the other end communicated with an external source of vacuum through a vacuum hose. A cylindrical extension unitarily extends from one end of the hollow body of the adapter and includes an annular projection. The shank has a corresponding annular groove to lockingly receive the annular projection in order to lock the adapter against axial displacement relative to the drill.