Two main hurdles persist towards the more extensive bench-to-bed side translation of non-parenteral polymeric micelles. The first pertains to their thermodynamically-driven disassembly under uncontrolled dilution conditions in the biological milieu and upon interaction with biomacromolecules (e.g., proteins). The second is related to the relatively poor understanding of the pathways by which polymeric micelles improve the bioavailability of the payload by mucosal routes (e.g., intestinal). In this work, a chitosan-g-oligo(N-isopropylacrylamide) (CS-g-oligo(NiPAAm)) copolymer was modified with non-cytotoxic amounts of protoporphyrin IX (PP), a planar molecule of amphiphilic character that undergoes self-aggregation in water by forming π-π stacked supramolecular structures, to induce micellization under disfavored conditions and to serve as a fluorescent tracer for the measurement of the micelle permeability across a model of the intestinal epithelium in vitro. Findings indicated that the conjugation of PP amounts as low as 2% w/w induced the formation of micelles at temperatures below the lower critical solution temperature of oligo(NiPAAm) (30-32 °C). Moreover, permeability studies conducted at both 4 °C and 37 °C strongly suggested that despite the relatively large size of the micelles (200-300 nm), they cross the epithelial monolayer mainly by a paracellular pathway due to the opening of tight junctions. Complementary uptake studies by flow cytometry indicated that no endocytosis, though due to passive or facilitated diffusion, some internalization takes place.