Experimental and numerical methods were used to investigate the aerodynamic performance of a winglet tip in a linear cascade. A flat tip and a cavity tip were studied as baseline cases. The flow patterns over the three tips were studied. For the cavity tip and the winglet tip, vortices appear in the cavity and the gutter. These vortices reduce the discharge coefficient of the tip leakage flow. The purpose of using a winglet tip is to reduce the driving pressure difference. The pressure side winglet of the winglet geometry studied in this paper has little effect in reducing the driving pressure difference. It is found that the suction side winglet reduces the driving pressure difference of the tip leakage flow near the leading edge, but increases the driving pressure difference from midchord to the trailing edge. This is also used to explain the findings and discrepancies in other studies. Compared with the flat tip, the cavity tip and the winglet tip achieve a reduction of loss. The effects of the rounding of the pressure side edge of the tips were studied to simulate the effects of deterioration. As the size of the pressure side edge radius increases, the tip leakage mass flow rate and the loss increase. The improvement of the aerodynamic performance by using a winglet remains similar when comparing with a flat tip or a cavity tip with the same pressure side radius.