A rolling bearing includes: a first raceway member; a second raceway member; rolling elements; a guide member; and a cage. The guide member is formed integrally with or separately from the second raceway surface, and includes: an annular guide surface arranged at a position different from a second raceway surface of the second raceway member in an axial direction; a flow path in which compressed air for supplying lubricating oil flows; and an annular groove provided in the guide surface in a circumferential direction. The annular groove has: a discharge opening connected to the flow path in a groove bottom part; and an introducing surface configured to introduce the compressed air toward the second raceway member in the axial direction. The annular cage holds the rolling elements and has a guided surface opposing the guide surface such that the guided surface can slidably contact the guide surface.