The interaction between ibuprofen and maltodextrins with different dextrose equivalent was studied in solution and solid state in order to investigate the effect on the solubility of ibuprofen and to determine their usefulness in terms of chiral recognition. Apparent binding constants were calculated using nuclear magnetic resonance spectroscopy experiments and solubility studies. The results showed an increase in the apparent solubility of ibuprofen in the presence of maltodextrins that depended on their ionization state. The freeze-drying method was used to prepare solid complexes, while physical mixtures were obtained by simple blending. These solid systems were characterized in the solid state using differential scanning calorimetry, thermogravimetric analysis, Fourier Transform-Infrared spectroscopy, scanning electron microscopy and X-ray diffractometry. Detailed nuclear magnetic resonance studies provided evidence of the influence of the type and concentration of the maltodextrin host on the chiral recognition of racemic ibuprofen, indicating that these linear ligands act as chiral selectors.