We thoroughly investigate and quantify the chemical stability of an imidazolium-based alkaline anion exchange polymerized ionic liquid (PIL), poly(1-[(2-methacryloyloxy)ethyl]-3-butylimidazolium hydroxide) (poly(MEBIm-OH), over a broad range of humidities, temperatures, and alkaline concentrations using the combined techniques of electrochemical impedance spectroscopy and nuclear magnetic resonance spectroscopy. High chemical stability was observed under dry conditions (10% RH) at 30 degrees C, humid and saturated conditions up to 80 degrees C, and even in mild alkaline conditions ([KOH] < 1 M) at 25 degrees C. Degradation was only observed under more vigorous conditions: dry conditions (10% RH) at 80 degrees C or at higher alkaline concentrations ([KOH] > 1 M). Under these conditions, we suggest an imidazolium ring-opening mechanism as the primary degradation pathway, based on a detailed analysis of the H-1 NMR spectra. Similar to poly(MEBIm-OH), other alkaline anion (carbonate (CO32-) and bicarbonate (HCO3-)) exchange PILs were also synthesized in this study via salt metathesis of the PIL precursor, poly(1-[(2-methacryloyloxy)ethyl]-3-butylimidazolium bromide) (poly(MEBIm-Br)). The thermal and ion conductive properties of each PIL in this study were characterized. The ionic conductivity of the hydroxide conducting PIL, poly(MEBIm-OH), was the highest of these PILs investigated at 9.6 mS cm(-1) at 90% RH and 30 degrees C with an Arrhenius activation energy of 17.1 kJ mol(-1) at 90% RH.