Playing chess as dream image usually refers to playing complicated and dangerous mind games. Also, consider the fact that when playing this difficult game one needs to carefully plan and think through every move - consequently, chess in dreams may be interpreted as a symbol for being rational and seeing things logically. One should learn not to act before thinking things through, before weighing the advantages and disadvantages of a certain action.
If you are sure to win a chess game in your dream, this image points to your rational nature. It may also foretell good luck and happy events to take place in your waking life, including a promotion to a higher position at work or a pay raise. On the other hand, if you are sure to lose the game, then you let yourself guided by feelings, emotions or primitive desires and this is where you go wrong - start using your mind to solve life problems or conflicts.
All in all, playing chess or seeing chess boards and pieces in a dream bears a positive significance and refers to one's intellectual abilities. We should not forget that chess used to be one of kings' favorite games, therefore it is a game of high, 'royal' origin.