Shared mobility-on-demand services are expanding rapidly in cities around the world. As a prominent example, app-based ridesourcing is becoming an integral part of many urban transportation ecosystems. Despite the centrality, limited public availability of detailed temporal and spatial data on ridesourcing trips has limited research on how new services interact with traditional mobility options and how they affect travel in cities. Improving data-sharing agreements are opening unprecedented opportunities for research in this area. This study examined emerging patterns of mobility using recently released City of Chicago public ridesourcing data. The detailed spatio-temporal ridesourcing data were matched with weather, transit, and taxi data to gain a deeper understanding of ridesourcing’s role in Chicago’s mobility system. The goal was to investigate the systematic variations in patronage of ridehailing. K-prototypes was utilized to detect user segments owing to its ability to accept mixed variable data types. An extension of the K-means algorithm, its output was a classification of the data into several clusters called prototypes. Six ridesourcing prototypes were identified and discussed based on significant differences in relation to adverse weather conditions, competition with alternative modes, location and timing of use, and tendency for ridesplitting. The paper discusses the implications of the identified clusters related to affordability, equity, and competition with transit.