Large eddy simulation (LES) is used to explore the boundary layer transition mechanisms in two rectilinear compressor cascades. To reduce numerical dissipation, a novel locally adaptive smoothing (LAS) scheme is added to an unstructured finite volume solver. The performance of a number of subgrid scale (SGS) models is explored. With the first cascade, numerical results at two different freestream turbulence intensities (Ti's), 3.25% and 10%, are compared. At both Ti's, time-averaged skin-friction and pressure coefficient distributions agree well with previous direct numerical simulations (DNS). At Ti = 3.25%, separation-induced transition occurs on the suction surface, while it is bypassed on the pressure surface. The pressure surface transition is dominated by modes originating from the convection of Tollmien–Schlichting waves by Klebanoff streaks. However, they do not resemble a classical bypass transition. Instead, they display characteristics of the “overlap” and “inner” transition modes observed in the previous DNS. At Ti = 10%, classical bypass transition occurs, with Klebanoff streaks incepting turbulent spots. With the second cascade, the influence of unsteady wakes on transition is examined. Wake-amplified Klebanoff streaks were found to instigate turbulent spots, which periodically shorten the suction surface separation bubble. The celerity line corresponding to 70% of the free-stream velocity, which is associated with the convection speed of the amplified Klebanoff streaks, was found to be important.