Designing chaotic systems with specific features is a hot topic in nonlinear dynamics. In this study, a novel chaotic system is presented with a unique feature of crossing inside and outside of a cylinder repeatedly. This new system is thoroughly analyzed by the help of the bifurcation diagram, Lyapunov exponents’ spectrum, and entropy measurement. Bifurcation analysis of the proposed system with two initiation methods reveals its multistability. As an engineering application, the system’s efficiency is tested in image encryption. The complexity of the chaotic attractor of the proposed system makes it a proper choice for encryption. States of the chaotic attractor are used to shuffle the rows and columns of the image, and then the shuffled image is XORed with the states of chaotic attractor. The unpredictability of the chaotic attractor makes the encryption method very safe. The performance of the encryption method is analyzed using the histogram, correlation coefficient, Shannon entropy, and encryption quality. The results show that the encryption method using the proposed chaotic system has reliable performance.