Neutral-atom quantum simulators provide a powerful platform for realizing strongly correlated phases, enabling access to dynamical signatures of quasiparticles and symmetry breaking processes. Motivated by recent observations of quantum phases in flux-frustrated ladders with non-vanishing ground-state currents, we investigate interacting bosons on the dimerized Benalcazar-Bernevig-Hughes (BBH) lattice in two dimensions—originally introduced in the context of higher-order topology. After mapping out the phase diagram, which includes vortex superfluid (V-SF), vortex Mott insulator (V-MI), and featureless Mott insulator (MI) phases, we focus on the integer filling case. There, the MI/V-SF transition breaks the ${\mathbb{Z}}_2^T$ and U(1) symmetries, where ${\mathbb{Z}}_2^T$ corresponds to time-reversal symmetry (TRS). Using a slave boson description, we resolve the excitation spectrum across the transition and uncover a chiral Higgs mode whose mass softens at criticality, providing a dynamical hallmark of emergent chirality that manifests via the oscillation of the loop currents in quench dynamics. Our results establish an experimentally realistic setting for probing unconventional TRS-broken phases and quasiparticles with intrinsic chirality in strongly interacting quantum matter.