This study outlines the experimental investigation methods of condition monitoring to predict bearing failures using the experimental vibration signatures. The purpose of condition monitoring is to maximize the machine availability and utility of the machine components. Bearings being one of the most common component in any rotating machinery, it is vital to study the health of the bearing and can predict bearing failure, its location and severity. This prevents machine downtime, monetary loss and unfortunate accidents. A test rig was fabricated to get the vibration signatures of bearings. Prediction of bearing failure relies on the presence of the bearing characteristic frequencies-inner race frequency, outer race frequency, ball pass frequency and fundamental train frequency-and its harmonics in the vibration signal acquired. These frequencies are present in the vibration signature due to the interaction of surfaces of different bearing components that have defects in them. Both time and frequency domain numerical signature analysis were performed on the vibration signatures acquired. Simple frequency domain method like Fast Fourier Transform (FFT), chaotic vibration method like modified Poincare mapping and time-frequency domain Wigner-Ville distribution (WVD) were used in detecting bearing failure. Using the FFT analysis method, it is hard to predict the failures, hence better signal processing methods like modified Poincare mapping and WVD are used. Also, it is observed that the chaotic vibration signatures found in the lower-order mechanical systems like bearings. With the chaotic analysis methods like, Poincare Mapping and Wigner-Ville Distribution, the location and the severity of the bearing failure can be predicted.