Recently varieties of user groups are formed as the number of people using cyber chatting gets increased and there are many changes in the range and field of its use. But because most of the cyber chatting systems are being operated to enlarge the additional sonics use, the using environments are stereotyped. And as its function is being various as well, it can not provide with a user-centered environment. So this thesis compares and analyzes the problems derived from the usability evaluation for solving the problems in using cyber chatting systems, and presents the guidelines of emotion-intended user interface design for improving the usability as the result of the analysis. First, this study investigates cyber chatting systems as a means of web communication tools through the existing literatures. Secondly, this study finds out the problems in using them through satisfaction evaluation, heuristic evaluation, performance evaluation, and observation evaluation and presents a way of solving the provisional problems in using them as the analysis of the result of usability evaluation. And this was proceeded for the purpose of applying and activating the better usability evaluation of cyber chatting systems later. Through the usability evaluation, it is found out that the structuralization of chatting function, the screen visibility by the size and arrangement of the compositional elements of a screen, and the improvement and development of the proper metaphor use of images and functions by the communication environment are necessary.