The health insurance Marketplaces established by the Affordable Care Act include features designed to simplify the process of choosing a health plan in the individual, or nongroup, insurance market. While most individual health insurance enrollees purchase plans through the federal and state-based Marketplaces, millions also purchase plans directly from an insurance carrier (off Marketplace). This study was a descriptive comparison of the decision-making processes and shopping experiences of consumers in two states who purchased a health insurance plan from the same large insurer in 2017, either through the federal Marketplaces or off Marketplace. In a survey, those who selected plans through the Marketplaces reported less difficulty finding the best or most affordable plan than did those enrolling off Marketplace. Respondents in families with chronic health conditions who enrolled through the Marketplaces reported better overall experiences than those who enrolled off Marketplace. Respondents with low health insurance literacy reported poor experiences in enrolling both through the Marketplaces and off Marketplace. Access to consumer assistance in the individual health insurance market should target off-Marketplace populations as well as all populations with low health insurance literacy.