At atmospheric pressure, the mole fraction solubility of 1,5-gluconolactone (GDL) in twelve pure solvents (methanol, ethanol, ethylene glycol (EG), n-propanol, i-propanol, n-butanol, i-butanol, t-butanol, acetone, acetic acid, acetonitrile, and dimethyl sulfoxide (DMSO)) was determined by the gravimetric method at 288.15–328.15 K and was positively associated with temperature. In alcohol solvents, the tendency towards molarity solubility at 318.15 K was as follows: EG > methanol > ethanol > t-butanol > i-propanol > n-propanol > n-butanol > i-butanol. In non-alcoholic solvents, the solubility sequence of GDL was DMSO > acetic acid > acetone > acetonitrile. Hirshfeld surface (HS) analysis and solute–solvent interaction energy were used to investigate the intermolecular interactions. The solvent effect was analyzed by the KAT-LSER model, which indicated that solute–solvent interaction had a great effect on solubility. In addition, the experimental values of solubility were correlated by three models (the modified Apelblat equation, van′t Hoff equation, and λh equation), and the corresponding relative deviation (RD), average relative deviation (ARD), and root-mean-square deviation (RMSD) were calculated. The applicability of three selected thermodynamic models was assessed by the Akaike Information Criterion (AIC). It can be concluded that the modified Apelblat equation was the best correlation model. Finally, the apparent thermodynamic properties of Gibbs energy, enthalpy, and entropy were computed using the van′t Hoff equation. All positive values demonstrated that the dissolution of GDL was a non-spontaneous, endothermic, and entropy-driven process.