An information processing apparatus includes a control unit that controls a first flying vehicle and a second flying vehicle. The first flying vehicle captures an image of a surface of a road. The second flying vehicle emits light onto the surface, such that a spot where a level difference is estimated, in advance, to occur on the surface, an image capturing direction in which the first flying vehicle captures an image of the spot, and a light emitting direction in which the second flying vehicle emits the light onto the spot have a relationship that causes, when the level difference exists, a shadow to occur at the spot and the shadow to be captured.