Chiral optical effects are generally quantified along some specific incident directions of exciting waves (especially for extrinsic chiralities of achiral structures) or defined as direction-independent properties by averaging the responses among all structure orientations. Though of great significance for various applications, chirality extremization (maximized or minimized) with respect to incident directions or structure orientations has not been explored, especially in a systematic manner. In this study we examine the chiral responses of open photonic structures from perspectives of quasinormal modes and polarization singularities of their far-field radiations. The nontrivial topology of the momentum sphere secures the existence of generic singularity directions along which mode radiations are either circularly or linearly polarized. When plane waves are incident along those directions, the reciprocity ensures ideal maximization and minimization of optical chiralities, for corresponding mode radiations of circular and linear polarizations, respectively. For directions of general elliptical polarizations, we have unveiled the subtle equality of a Stokes parameter and the circular dichroism, showing that an intrinsically (geometrically) chiral structure can unexpectedly exhibit no optical chirality at all or even optical chiralities of opposite handedness for different incident directions. The framework we establish can be applied to not only finite scattering bodies but also infinite structures, encompassing both intrinsic and extrinsic optical chiralities. We have effectively merged two vibrant disciplines of chiral and singular optics, which can potentially trigger more optical chirality-singularity related interdisciplinary studies.