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 adverse impacts of unexpected disruptions. This in turn can improve the experience and retention of current riders and help attract new ones. While previous studies have relied primarily on data collected from surveys to understand people’s use of transit information services, this paper uses backend data from Transit, a multimodal trip planner smartphone application (app), to analyze usage patterns in Calgary over the span of six months. A clustering analysis was initially performed to gain an understanding of trip search characteristics. The results show that most searches were made for short distanced trips. Additionally, panel data models were 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 markedly. Furthermore, there was found to be a significant increase in searches after the network was restructured and three bus rapid transit (BRT) lines were introduced. These findings can help agencies determine the best way to deliver information to people and gain insights into travel behavior.