What version of Google Chrome do you need for the PDF export to work? I tried it on 58.0.3029.96 (Linux) and this does nothing (no error messages, it just quits without writing any files):

$ google-chrome --headless --disable-gpu --print-to-pdf 'http://example.com'

Edit: I'm completely baffled that such widely used software as Google Chrome can have this written in the man page: "Google Chrome has hundreds of undocumented command-line flags that are added and removed at the whim of the developers."