We study nonlinear phenomena of bistability and chaos at a level of few quanta. For this purpose we consider a single-mode dissipative oscillator with strong Kerr nonlinearity with respect to dissipation rate driven by a monochromatic force as well as by a train of Gaussian pulses. The quantum effects and decoherence in oscillatory mode are investigated on the framework of the purity of states and the Wigner functions calculated from the master equation. We demonstrate the quantum chaotic regime by means of a comparison between the contour plots of the Wigner functions and the strange attractors on the classical Poincare section. Considering bistability at low-limit of quanta, we analyze what is the minimal level of excitation numbers at which the bistable regime of the system is displayed? We also discuss the formation of oscillatory chaotic regime by varying oscillatory excitation numbers at ranges of few quanta. We demonstrate quantum-interference phenomena that are assisted hysteresis-cycle behavior and quantum chaos for the oscillator driven by the train of Gaussian pulses as well as we establish the border of classical-quantum correspondence for chaotic regimes in the case of strong nonlinearities.