With advances in information technology, online shopping for a parcel (retail), grocery, and food (i.e. prepared meal) have become a part of daily life and they are expected to continue to grow in the future. Accordingly, shopping behaviors, i.e. shopping channels, are becoming more complex than ever. However, the current research focus is still mainly on traditional parcel delivery and little is known for food and grocery deliveries and their impacts on transportation systems. To have a better understanding of deliveries and their impacts on transportation systems, using the survey data from NYC DOT Citywide Mobility Survey in 2018, this paper investigated (a) factors affecting the three types of deliveries (retail, grocery, and food) by developing a seemingly unrelated model, and (b) the relationships between deliveries and in-store shopping trips by different modes using multiple simultaneous equations models. The results showed that factors affecting deliveries vary by the type of delivery, and the three deliveries are positively correlated by common unobserved factors. In addition, the relationships between delivery and shopping trip vary not only by delivery type but also by trip mode (driving/walking). The findings would provide valuable insights into travel demand modeling and curbside management.