The chatpad comes with its own headset that does plug in properly, no? I got my chatpad in a package with some other things (headset with different plug, Xbox Live 13 month card, and PGR4).
Whatever the case, I use a third-party headset that works with the chatpad since the regular Microsoft wired ones keep breaking on me even with no abuse or damage.
EDIT: I'm an illiterate dumbass and just realized you were talking about the wireless one. Forget I said anything.
Seems stupid of Microsoft to not make sure their own devices work together though...WTF.