Differences in cognitive abilities affect search behaviors, but this has mostly been observed in laboratory experiments. There is limited research on how users search for information in real‐world, naturalistic settings and how real‐world search behaviors relate to cognitive abilities. In this study, we investigated a wide range of behavioral data captured from real‐life search tasks, their association with users' cognitive abilities, and the potential for automatically inferring cognitive abilities from these data. Furthermore, we aimed to determine the data quantity and monitoring duration needed to effectively estimate cognitive abilities from naturalistic behavior. Twenty individuals with βvarying cognitive abilities participated in the experiments in which their everyday search behavior was continuously recorded for 14 days. Their cognitive ability was evaluated through standard tests conducted individually. Data consisted of over 800 h of monitoring, including 2022 queries extracted from 1,442,447 screen frames and associated operating system logs. Using these data, naturalistic search behaviors were associated with cognitive abilities, and predictive models were trained. The results showed that lower selective attention was found to be associated with longer dwelling on selected search results. Faster psychomotor speed and higher fluid intelligence were found to be associated with a greater amount of text read on selected pages. Predictive models exhibited small error rates in predicting cognitive abilities.