We study the nature of quantum phase transitions out of Z4 ordered phases in quantum loop models on a zig-zag ladder. We report very rich critical behavior that includes a pair of Ising transitions, a multi-critical Ashkin-Teller point and a remarkably extended interval of a chiral transition. Although plaquette states turn out to be essential to realize chiral transitions, we demonstrate that critical regimes can be manipulated by deforming the model as to increase the presence of leg-dimerized states. This can be done to the point where the chiral transition turns into first order, we argue that this is associated with the emergence of a critical end point.