This How To applies to either Windows or Mac version of iTunes.
By default, iTunes allows you to burn playlist to a disc. You have the option further to create an audio CD, MP3 CD, or Data CD or DVD. But there's no option to transfer a playlist to a USB drive from the iTunes menus.
But the method is actually a rather simple one. Just open the playlist you like to transfer and select all the music files in the right pane of iTunes, then click and drag to the USB drive window, either in File Explorer for Windows or Finder for Mac.
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