I have a simple test jekyll app like so:
index.html is:
Here's a summary of what I've found while solving this in 2014:
Started with
https://github.com/donaldducky/jekyll-cssminify
Development was going well until it was beat by this project:
http://www.matthodan.com/2012/11/22/jekyll-asset-pipeline.html
...which so far has been my favorite to implement, except it doesn't work now and it looks like development has been halted, so I was forced to turn to
https://github.com/envygeeks/jekyll-assets
...which again, beats #2 but is just a touch trickier to use. Anyway, that's the only one that works, so that's what I'm using now.