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I doubt very much you'd ever get a program like calibre to run on a chromebook. ChromeOS is artificialy restricted to run simple client apps that connect to a (usually google) server to do all the real work, with the nice side effect that the server operator (usually) gets to own all your data.
Your best option is to uncripple your chromebook by installing a real linux operating system on it.
Failing that, you would need to run the calibre content server on a server and connect to it with Chrome on the Chromebook. The problem with that is that the calibre content server is currently read only. It is on my TODO list to change that.
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