The interaction of a swimmer with unsteady vortices in complex flows remains a topic of interest and open discussion. The present study, employing the immersed boundary method with a flexible fin model, explores swimming behaviours behind a circular cylinder with vortex-induced vibration (VIV). Five distinct swimming modes are identified on the
$U_r$–
$G_0$ plane, where
$U_r$ denotes the reduced velocity, and
$G_0$ represents the fin’s initial position. These modes include drifting upstream I/II (DU-I/II), Karman gait I/II (KG-I/II), and large oscillation (LO), with the DU-II, KG-II and LO modes being newly reported. The fin can either move around or cross through the vortex cores in the KG-I and KG-II modes, respectively, for energy saving and maintaining a stable position. When the upstream cylinder vibrates with its maximum amplitude, a double-row vortex shedding forms in the wake, allowing the DU-II mode to occur with the fin to achieve high-speed locomotion. This is attributed to a significant reduction in the streamwise velocity caused by vortex-induced velocity. Furthermore, a symmetry breaking is observed in the fin’s wake in the DU-II mode, potentially also contributing to high-speed locomotion. Overall, compared to the case without an upstream cylinder, we demonstrate that a self-propelled fin gains hydrodynamic advantages with various swimming modes in different VIV wakes. Interestingly, increased power transferred from flows by the oscillating cylinder leads to a more favourable environment for the downstream fin’s propulsion, indicating that a fin in VIV wakes obtains more advantages compared to the vortex street generated by a stationary cylinder.