Working with his cousin Bianca, and his parents' friend King Kaleidoscope, they travel across the countryside while engaging in a series of minigames, which demonstrate chess piece movements, such as a Ms. Pac-Man-style game demonstrating the rook's horizontal and vertical movements, and a sumo wrestling game based on the concept of king opposition.
When reaching each piece of equipment, a cutscene shows Chesster explaining the games to Fritz and Bianca and then the player has the opportunity to play.
At the Pleasantville Village Olympics, the player takes part in timed games involving movements that resemble that of a knight fork and bishop skewer.
They begin to use his chess training machines and accumulate "ELO" creatures as their ability improves, which they need in order for a sensor in the elevator to allow them to journey upwards.
They challenge King Black to a duel and a television segment plays depending on whether the user wins or loses.
They also play Chesster's flea circus attraction, in which they have to place a piece on the board such that black is in checkmate under time pressure.
The game takes place on an alien planet, in which Fritz and Bianca learn additional tactics and strategies.
They learn about the Queen's Gambit, blockades, additional checkmate patterns, passed pawns, the concepts of space and tempo, drawing strategies and variants including dice chess.
[6] Hope Katz Gibbs of The Washington Post praised Part 1 as a "clever teaching tool" which divides learning chess into "small, kid-friendly lessons".
[4] Brian Wilson of School Library Journal wrote that Part 1 has "an overlong story, too much dialogue, and some confusing directions" but is "humorous" and "mostly successful" in teaching chess.
[2] The New York Times' Charles Herold reviewed Part 2 positively, calling the graphics "appealing" and the dialogue "amusing", while finding that it was "the most entertaining way" he knew of to improve one's chess.
[7] Karen Yannacio of Parenting for High Potential said that she was "impressed with the training modules" of Part 2 and believed that its graphics were "incredibly appealing and fun".