Polyvinyl chloride (PVC) tubing is a vital part of many industries, including the medical and food sectors. The ability to chemically modify PVC has previously been reported mainly on powdered or rigid forms of the plastic. Here, we describe the chemical modification of flexible PVC tubing with azide (and the attempted modification with cyanide) facilitated by phase transfer catalysts and characterization of the resulting materials. These modifications provide convenient handles for click chemistry linkages via azide-akyne cycloaddition, which allows for diverse surface functionalization of PVC for a variety of applications.