This works for me:
start chrome --enable-logging --headless --disable-gpu --print-to-pdf=c:\misc\output.pdf https://www.google.com/
… but only with “start chrome” and “–enable-logging” and with a path (for the pdf) specified – and if the folder “misc” exists on the c-directory.
Addition: … the path for the pdf – “c:\misc” above – can of course be replaced with any other folder/dir.