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The knowledge of all occupied and unoccupied trips made by selfemployed drivers are essential for optimized vehicle dispatch by ride-hailing services (e.g., Didi Dache, Uber, Lyft, Grab, etc.). However, vehicles’ occupancy status is not always known to service operators due to adoption of multiple ride-hailing apps. In this paper, we propose a novel framework, Learning to INfer Trips (LINT), to infer occupancy of car trips by exploring characteristics of observed occupied trips. Two main research steps, stop point classification and structural segmentation, are included in LINT. In the first step, we represent a vehicle trajectory as a sequence of stop points, and assign stop points with pick-up, drop-off, and intermediate labels thus producing a stop point label sequence. In the second step, for structural segmentation, we further propose several segmentation algorithms, including greedy segmentation (GS), efficient greedy segmentation (EGS), and dynamic programming-based segmentation (DP) to infer occupied trip from stop point label sequences. Our comprehensive experiments on real vehicle trajectories from self-employed drivers show that (1) the proposed stop point classifier predicts stop point labels with high accuracy, and (2) the proposed segmentation algorithm GS delivers the best accuracy performance with efficient running time.