Ibuprofen is a Biopharmaceutical classification system class II drug that exhibits poor dissolution rate in the gastrointestinal tract. The aim of the present study is to enhance the dissolution of ibuprofen in presence of glucosamine. To this end, different ratios of ibuprofen:glucosamine were dissolved in various organic solvents to obtain the solid dispersions of ibuprofen–glucosamine mixtures. The solid state analysis of the samples (differential scanning calorimetry, Fourier infrared spectroscopy and X-ray powder diffraction) and the morphology (scanning electron microscope) were investigated. Particle size analysis and in vitro dissolution studies showed that the type of solvent has a significant influence on dissolution rate. Ibuprofen–glucosamine solid dispersions obtained from acetone produced better dissolution compared to that of other organic solvents. The effect of water in binary mixtures of either acetone or ethanol was also explored and the results showed that when the ratio of acetone to water was 75:25, the highest dissolution was obtained. Solid state analysis ruled out any chemical interaction between the drug and carrier even in the presence of various organic solvents which indicates a good stability of the solid dispersions to enhance the dissolution rate of ibuprofen. It was also investigated via XRPD analysis that the ibuprofen retained its crystallinity without any adverse effect on the dissolution rates. In conclusion, the present study showed that a manipulation of the organic solvent:water ratio and a change in the type of organic solvent impacted on ibuprofen–glucosamine achieving very high dissolution rate without compromising its crystallinity and physical stability.