Yes, you can use Chirp on the command line:
https://github.com/tylert/chirp.hg
I use a Raspberry Pi Zero W as a headless chirp updater (for my mobile radio). I keep my chirp files saved in a Dropbox folder with public URLs - this way I can edit from the GUI on my desktop and then fire up the Raspberry Pi in the car (using my phone's hotspot feature) so it can pull the latest chirp images from Dropbox (via wget) and update the radio using command line chirp. I'm still working on the README but here's my files for putting it all together:
https://github.com/tycen/chirpi
I just call the updater script from cron on reboot.
-Tycen