The need to function in multilingual environments and the fact that study abroad (SA) is believed to be one of the most efficient language learning contexts (Collentine, 2009) have boosted the popularity of SA programs. While numerous recent studies have examined the SA impact on oral fluency, vocabulary or writing, among others, certain areas, such as listening skills (Llanes, 2011), have yet to receive substantial attention. In an attempt to address this issue, a pretest-posttest design study was conducted to gauge the listening skills of 12 college students at the beginning and the end of a 5-week SA experience in Costa Rica. Results from non-parametric tests revealed that despite the brief duration of the program, participants’ overall listening comprehension improved significantly. Individual analysis revealed that significant gains emerged in exit tasks in which the topic of conversation was kept consistent, suggesting that contextualization plays a crucial role in input comprehension.