I don't know anything about the research on the academic benefits of chess, but it is a fun game and certainly it helps one to think in a rule-governed way, which seems like excellent preparation for math and other formal thinking. So with H. I began showing him the pieces when he was two, and we got "No Stress Chess" when he was three or so. In this way he learned how to set up the board. In the last few years we've played a game a week or so, and I explain things of course as we play. Lately we've been reading a couple of intro chess books for kids--he wouldn't have been able to get through them until recently, I'm sure. Also, we do chess tutorial software, which H. tolerates (he doesn't love it, but he doesn't resist either).
Of course, you have to remember that the chess club players are pretty much the lowest on the social totem pole especially in high school, so if you want to get into chess, you can't really care much about that. Fortunately for us, we don't.