It's probably very hard. I wouldn't try it unless you want to spend a week or two on it, and you're comfortable with gentoo linux. A few ideas for developers who want to try it: a) make sure your system has an Intel x86-compatible processor; wine won't do much for you on ARM processors b) flip your chromeos system into developer mode, e.g. http://www.chromium.org/chromium-os/developer-information-for-chrome-os-devices/samsung-series-5-chromebook c) transfer some simple binaries from a similar desktop linux system, and see if they work d) if that works, try transferring wine Alternately, e) build chromium OS yourself; see http://www.chromium.org/chromium-os/developer-guide f) then try building wine; maybe see http://www.chromium.org/chromium-os/how-tos-and-troubleshooting/portage-build-faq