Apple only supports their rip-off version of FLAC, ALAC. Get something like dbPowerAmp and convert the FLAC files to ALAC or AIFF...
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JRiver should have their Apple version ready soon, it's currently in Beta and by all accounts is already working very well and sounds superb.
JRiver blog and download (you can follow progress there).
The Win version is terrific, better sound than others we've compared to. I will be installing JRiver on my Mac Mini and looking forward to not having to depend on iTunes wonky rules and limited format choices (not to mention bad sound).
JRiver will allow Apple to play FLAC, Apple Lossless, Wav or whatever you have. It's less expensive than Channel D and Amarra, both of which I own and JRivers has an application to operate remote with iPad, iPhone and other devices.
I normally use XLD to convert FLAC to AIFF. AIFF is uncompressed lossless like WAV but supports meta data.
You can use apps like PureMusic or AudirvanaPlus which works alongside iTunes and allows you to drag any existing FLAC file to be added to the iTunes library and can be played by iTunes (provided the app is running in the background)
Like the most of folks -- and recognizing that you're not interested in converting to AIFF -- that's what I do.
Depending on how much material you're talking about, it's not a big deal. I use Max, which is free and easy.
Over at Computer Audiophile, they have an instruction video wth commentary here, which I found helpful when getting started.
In short, think your options are to either amend your current setup or convert the files.....
Audirvana has a method whereby it imports flacs into itunes via a proxy file - see page 10 of their manual on how to do this.
There appears to be one caveat at present and I've told them about it - you have to have the flacs on the computer's hard drive.
I originally had the flacs on my NAS drive and Audirvana could not link the proxy to the file.
The Audirvana interface identifies the file being played as flac
Sounds fantastic - and I no longer have to convert - bluddy brilliant :-)
Audirvana support was fantastic - same day response with a problem resolution!
How's them Apples! :-)
UPDATE - it appears there are a few glitches with Audirvana...
If you put some titles in a playlist and let it cycle round - when it returns to the start it plays the track at half speed
Selecting a track outside of the playlist fixes that.
Provided feedback - hopefully a fix will be coming
Back to the toons :-)
The best solution is to use software other than iTunes if one isn't dependent on it for some reason. Many software packages offer Airplay if that is important.
I have most of my library in FLAC but a good portion in AIFF. AIFF is a nice solution all around if storage and transcoding isn't a big deal. I own all the "audiophile" suites and use Audirvana the most when I am at my computer at home (with iTunes integration). When interacting with my main system, I usually use Media Centre and at work I use Decibel (simple, fast and functional).
Each solution permits FLAC but no seamless FLAC integration with iTunes. The seamless adjective is important. All the solutions above offer work-arounds (or in some cases just better software outright) but iTunes is a slick piece on a Mac. It really is tough to beat if one's music is ALAC or AIFF.
Transcoding seems like the best option frankly. ALAC and AIFF can be played on almost any system using a wide variety of players. Using XLD to convert FLAC to ALAC or AIFF and delete the FLACS in the process makes the entire endeavor very painless. XLD also offers the ability to add music to iTunes after each file is parsed.
UPDATE: the problem I reported above seems to have fixed itself - once I rebooted the iMac - typical Apple
Everything is now playing as it should
Just reboot after installing Aurdirvana if you experience problems - You should probably reboot after installing all programs knowing Apple
Damien (of Audirvana support) could not replicate the problem