The COVID-19 pandemic has highlighted the importance of information and communication technologies (ICTs) in providing virtual engagement. Planners and engineers must determine whether cities will see reductions in travel demand, given the increasing use of ICTs. Notably, ICTs facilitate online shopping and working from home (WFH). Generally, online shopping may lead to fewer shopping trips; similarly, WFH may reduce work-related trips. However, more WFH has the potential to generate other non-work trips, including shopping trips. To find answers and explore interdependencies, this study integrates pre-pandemic behavioral data with during-pandemic travel data. In our framework, WFH and online shopping are considered together. By harnessing the pre-pandemic 2017 National Household Travel Survey data, this study jointly analyzes the relationships between shopping trips, online shopping, and WFH with a conditional mixed process model that can address unobserved endogeneity and selection bias. The results suggest that, before the pandemic, online shopping was associated with fewer in-person shopping trips while WFH was associated with more shopping trips. The role of socio-demographic, locational, and travel-related factors is also explored. The during-pandemic data and analysis capture how COVID-19 affected travel behavior. Results show that the relationships among the key variables found in the pre-pandemic data are similar but differ in magnitude from during the pandemic. WFH increased from 12% to 61% during COVID-19, admittedly an unusual situation. In the next “new normal,” planners may improve travel demand models by treating WFH explicitly as an alternative to traveling to work in the trip generation and time of day models.