Relevant and timely provision of transit information advises travelers of the route options available to them, allows riders to plan the timing of their trips, and helps mitigate the impact of unexpected disruptions. This study uses data from Transit, a multimodal trip planner smartphone application, to analyse usage patterns in Calgary over the span of six months. From the cluster analysis, it was found that the most common searches made in Transit were for shorter distanced trips. Additionally, panel data models are estimated to investigate the relationship between search frequency and transit service characteristics, temporal factors, built environment, weather and sociodemographic attributes. The model results reveal that people seek out transit information the most during times of uncertainty, as poor reliability and service disruptions were shown to increase itinerary searches. These findings can help agencies determine the best way to deliver information to people and gain insights into travel behaviour.