Poly(vinyl chloride), PVC, was aminated via reaction with ethylenediamine before conjugation with functionalized chitosan (Cs) using chloroacetyl chloride as a linking agent. Cs was functionalized with p-nitrophenyl (MA), p-anisyl (MB), and p-toluyl (MC) maleamates. Functionalized Cs-PVC conjugation was effected in the presence of AgNO3 (3% w/w) producing MA-CCs-PVC/Ag nanocomposites via a one-pot synthesis method. The chemical structures of the synthesized samples were studied by FTIR spectroscopy. Scanning and transmission electron microscopy were performed to investigate the morphology of the nanocomposites, while the EDX spectrum determined Ag contents in the prepared samples. Values of water uptake measurements determined the swelling properties of the prepared nanocomposites. The antibacterial efficiency of the modified polymers was investigated against two Gram-positive (Bacillus subtilis and Staphylococcus aureus), and two Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria, in comparison with that of Cs, amino-PVC (Am-PVC), and ampicillin as a reference antibacterial agent.