In the past decade, transportation network companies (TNCs) such as Uber, Lyft, and Via have established themselves as a viable transportation alternative to other modes. However, the popularity of these services has come with a fair share of criticism for their negative externalities such as increasing vehicle miles traveled and congestion in cities. Pooled ride-hailing trips, in which all or a part of two individual (or group) trips are combined in and served by a single vehicle, have the potential to reduce these externalities. Pooling of rides is an effective solution to reduce congestion and travel cost, but pooled rides still represent a small percentage of the total trips served (and miles driven) by TNCs relative to single-occupancy (and without customer) vehicle miles. Both TNCs and cities alike will benefit from understanding what factors encourage or deter pooling a ride-hailing trip. In this study, newly available Chicago transportation network provider data were explored to identify the extent to which different socioeconomic, spatiotemporal, and trip characteristics affect willingness to pool (WTP) in ride-hailing trips. Multivariate linear regression and machine-learning models were employed to understand and predict WTP based on location, time, and trip factors. The results show intuitive trends, with income level at drop-off and pickup locations and airport trips as the most important predictors of WTP. Results from this study can help TNCs and cities devise strategies that increase pooled ride-hailing, thereby reducing adverse transportation and energy impacts from ride-hailing modes.