You can convert your FLAC files into Apple Lossless (ALAC) - iTunes' lossless format - in one easy operation, preserving your metadata.
Here's how you could go about it:
- Download and install dbPowerAMP (there's a 21 day trial available at
www.dbpoweramp.com)
- Also download and the ALAC and FLAC codecs from the Codec Central section of the website
- Open the 'Batch Converter' from the Start Menu group
- Select the folder containing your FLAC files
- Click 'Convert', tell it to use ALAC as the output format, and tell it where to put them
- Leave it for however long it takes
- Transfer those to the Mac
- Optionally, enable the 'copy files when added' option in the Advanced tab of iTunes Preferences (depends how you want things organised)
- Drag the files into iTunes
... and you're done.
You may want to download foobar2000 (
www.foobar2000.org) and its ALAC codec to double-check that no metadata was corrupted during the conversion process - add the music into a playlist and it'll show you all the metadata. Incidentally, while I have done this before myself, I don't recall if it saved coverart - but iTunes' coverart search will help to a certain degree if it doesn't.
If any metadata was damaged (I have found that tags with Unicode characters are not always maintained), you can use MusicBrainz' (
www.musicbrainz.org) 'Picard' tool to automatically add the metadata back (well, in the majority of cases anyway!) - drag the ALAC files from foobar in to the top of the left pane, then select them and click 'Scan' at the top - and as Picard fingerprints the files, they should appear in the right-hand pane. Organise them manually if it gets them wrong, then select them and click 'Save'. There's a more in-depth userguide on the website - that's only skimming the surface. Keeps my files in check with minimal effort. =D
At this point you can either delete or backup your original FLAC files.
EDIT: Oh, unfortunately this won't save your star ratings, play counts, skip counts, or any extended metadata from Media Center - there's no immediate method of moving this data across to iTunes easily. All you'll get into iTunes is the basic metadata.