While Chrome OS can run a linux virtual machine and you can install checkra1n, you cannot use it because you can't give it usb access to your device. In this tutorial, we're going to enable usb booting on your chromebook and then boot into checkn1x, a tiny linux distribution that you can run from a usb drive that has checkra1n and everything it needs to run pre-installed.
Before continuing, make sure you have a usb flash drive that you don't mind erasing as this process WILL WIPE ALL DATA ON THE DRIVE.
Enabling or disabling developer mode will wipe your chromebook. Most things like extensions, apps, docs, slideshows and such are saved to your google drive automatically and aren't saved locally. Anything stored locally however, such as things in the “My files” tab will be gone unless you upload them somewhere else, such as your google drive.
This process is the same on nearly all chromebooks but if it doesn't work for you, google “enable developer mode