For the life of me I couldn't get an index.css.map to load today. I'm using the latest stable release (Chrome 43.0.2357.124 m) on Windows 7. I ended up creating a small test project - an index.html with an index.less which imports 2 other .less files and is processed to an index.css + index.css.map. I've attached all sources here. When I check Dev Tools > Network I only see the index.html and index.css loading - no index.css.map.
I tested the site in Firefox and it works (index.css.map loads). Then I got out an old laptop and accessed the site running on my newer laptop and ... it worked! the index.css.map was loaded by Chrome on the old laptop. Luckily before Chrome updated on the old laptop I was able to take a screenshot - the old laptop was running 37.0.2062.103 m. Now that the old laptop has updated to the latest stable release of Chrome the index.css.map has stopped loading on the old laptop as well.
Hence my conclusion - the latest stable release has broken the css source map functionality.
It seems weird that I'd be the first to notice - so to be on the safe side I've attached my test project to this report.