Various fields and commercial sectors have witnessed a transformation with the advent of the internet. In the last decade, the retail sector in particular has witnessed the massive growth of e-commerce. This has also significantly altered our shopping experiences, influencing a range of decisions, from where, how, and how much to shop. With the consistent growth of e-commerce transactions, more trucks than ever before are entering cities today, bringing with them the negative externalities of increased congestion and pollution. This study first unravels underlying shopping behaviors–both in-store and online–using the 2016 American Time Use Survey (ATUS) data. The authors also develop an econometric behavioral model to understand the factors that affect shopping decisions. At a macro level, the disaggregate individual shopping behaviors are studied by implementing the model to synthetic populations to estimate potential vehicle miles traveled and environmental emissions in two metropolitan areas, Dallas and San Francisco (SF). Finally, the study estimates the impacts of rush deliveries, basket size, and consolidation levels by developing a breakeven analysis between in-store and online shopping. These results confirm the importance of managing the urban freight system, including delivery services and operations, to foster a more sustainable urban environment.