The 1H NMR spectra of 10-5 mole fraction solutions of 1-decyl-3-methyl-imidazolium chloride ionic liquid in water, acetonitrile, and dichloromethane have been measured. The chemical shift of the proton at position 2 in the imidazolium ring of 1-decyl-3-methyl-imidazolium (H2) is rather different for all three samples, reflecting the shifting equilibrium between the contact pairs and free fully solvated ions. Classical molecular dynamics simulations of the 1-decyl-3-methyl-imidazolium chloride contact ion pair as well as of free ions in water, acetonitrile, and dichloromethane have been conducted, and the quantum mechanics/molecular mechanics methods have been applied to predict NMR chemical shifts for the H2 proton. The chemical shift of the H2 proton was found to be primarily modulated by hydrogen bonding with the chloride anion, while the influence of the solvents-though differing in polarity and capabilities for hydrogen bonding-is less important. By comparing experimental and computational results, we deduce that complete disruption of the ionic liquid into free ions takes place in an aqueous solution. Around 23% of contact ion pairs were found to persist in acetonitrile. Ion-pair breaking into free ions was predicted not to occur in dichloromethane.