This article provides an examination of interrelationships among educational technology, creativity, and chess. It presents the argument that chess training fosters significant gains in scholastic achievement and cognitive ability. As a vital component in chess training programs, contemporary chess software such as Fritz serves as impressive educational technology that can teach and monitor chess training as well as provide opportunities to practice chess, to diagnose errors, and to assess chess performance. Creativity is highly valued in the international chess community at the levels of chess moves, sequences of chess moves, and entire chess games. The artificial intelligence component of contemporary chess software is so formidable that such software can identify many creative chess moves, but not all. Chess is a domain where artificial intelligence encroaches onto the realm of creativity.