We report a family of novel macrocyclic anion transporters exhibiting exceptional chloride over proton/hydroxide ion transport activity. This is achieved by combining halogen bonding anion binding with anion encapsulation provided by a macrocyclic ionophore structure. By merging these two concepts we achieve a remarkable chloride over hydroxide selectivity of over 300-fold, while maintaining excellent overall activity. The short and convergent synthetic procedure utilising click chemistry renders these scaffolds an attractive access point for studying chloride transport in biological systems, as well as allowing for future optimisation of physicochemical properties.