The application of a flapping wing mechanism offers a vast range of development possibilities for unmanned aerial vehicles (UAVs) and autonomous underwater vehicles (AUVs). The influence of wake transitions on flapping wing mechanism's capabilities is not fully understood particularly at low Reynolds numbers. The numerical investigation of a symmetric airfoil performing sinusoidal heaving oscillations is performed to explore the wake transitions. The influence of heaving parameters on wake transitions when exposed to a constant velocity flow is investigated. The existence of reverse von Karman vortex street, defiected wake and chaotic wake is observed. The wake deflection is found to switch its direction before transforming into a chaotic wake. The coherent structures and its evolution with the flow are presented using proper orthogonal decomposition (POD). The underlying structures and their interactions for different wake situations are identified. Correlations for the nondimensional maximum velocity in the wake in terms of frequency and amplitude is proposed. The wake dynamics is found to depend significantly on the leading edge vortices. The time-varying velocity fluctuations in the flow field are presented and discussed in detail. The velocity fluctuation contours are used to identify the regions of momentum transfer. The transient nature of the flowfield is studied using the phase plot. A transition route from the periodic to chaotic regime though a quasi-periodic regime is established using time series analysis. The wake transitions are observed to be more sensitive towards heaving frequency than the heaving amplitude. © World Scientific Publishing Company