In this study, we evaluated the ability of computational cognitive models of web‐navigation like CoLiDeS and CoLiDeS+ to model i) user interactions with search engines and ii) individual differences in search behavior due to variations in cognitive factors such as aging. CoLiDeS and CoLiDeS+ were extended to predict user clicks on search engine result pages. Their performance was evaluated using actual behavioral data from an experiment in which 2 types of information search tasks (simple vs. difficult), were presented to younger and older participants. The results showed that the model predictions matched significantly better with the actual user behavior on difficult tasks compared to simple tasks and with younger participants compared to older participants, especially for difficult tasks. Also, the matches were significantly better with CoLiDeS+ compared to CoLiDeS, especially for difficult tasks. We conclude that the advanced capabilities of CoLiDeS+, such as incorporating contextual information and implementing backtracking strategies enable it to predict user behavior significantly better than CoLiDeS, especially on difficult tasks. The usefulness of these modeling outcomes for the design of support systems for older adults is discussed.