I realize this is an old thread, and the post I am about to comment on is > 2 years old. But just in case it is helpful ... if anyone else is planning to make a wooden chessboard, the "classic" way to do it is first to glue up "stripes" of wood, alternating the light and the dark, 4 of each. The width of each piece ("stripe") is the desired size of the square, but the length must be more than 8 times the size of the square. After the glue up has dried, the piece is turned 90° and sliced up into strips, each of which is just a bit wider than the final square dimension. Clean these up to the final dimension, then assemble and glue by flipping every other strip 180°.
Hmm ... trying to describe that in words is clear as mud, but I don't have any pictures from way-back when I last made a chess board. Maybe I can mock something up if anyone is interested ...