Unstable cutting in micromilling could severely damage the tool and hinder the possibility to a usable machined part. This study proposes an experimental correlation between cutting stability, acoustic emission (AE) signal and roughness profile in micro-end milling operations. The monitoring of cutting stability occurred over the micromilling of two different grain-sized mid-carbon steel. The results have shown that the grain size influences the amplitude of AE signal. The root mean square of AE (AErms) has an expressive rise when performing unstable cutting in both workpiece materials, influencing the roughness surface levels. The index proposed to correlate the AErms data to the cutting stability is experimentally validated and a new threshold for chatter and chatter-free cut is proposed. Although AE in-process monitoring is feasible for recognizing chatter occurrence in micromilling operations and general profile patterns, an overall prediction of surface roughness depends on more than AE data.