An imaging apparatus includes: an imaging unit that generates image data; a feature information generation unit that generates feature information smaller in data amount than the image data, the feature information indicating features of a subject image included in an image corresponding to the image data; an imaging-side first and second communication units; a communication status determination unit that determines the status of communication between an external communication device and the imaging-side first communication unit; and an imaging-side communication control unit that transmits the feature information to the communication device via the imaging-side second communication unit when the status of communication between the communication device and the imaging-side first communication unit is not favorable.