This paper describes an exploratory usability study designed to investigate how college students locate information in a Learning Management System and to establish a set of guidelines for creating the best course layouts that can increase the student’s learning experience. Using observations, perception survey data, and a high-fidelity eye-tracker that recorded where participants’ eyes focus, this study analyzed college students’ (n = 28) behavior and perceptions toward two different types of course layouts in Blackboard: functional and chronological. Students in the Functional group completed a set of typical instructional activities slightly faster overall than participants in the Chronological group. However, students in the Chronological group reported a higher ease of use and needed less help completing the activities. The implications from this study suggest the ideal course layout is a balance of both functional and chronological elements, as presented in this paper as a set of practical guidelines.