This qualitative study explores the flight experiences of obese people. The in-depth semistructured interviews (n = 24) with self-identified obese people revealed that they confront difficulties and barriers that arise from their interaction with the physical environment. While these entail some inconvenience, it is mostly the interaction with the social environment that results in a sense of embarrassment and humiliation. The aforementioned have an adverse effect on the flight experience. The flight is perceived as a three-part experience—boarding, flight, and deplaning—affected by mediating factors such as the staff approach, participants’ appearance, and the flight attributes (e.g., short/long, direct/indirect). An important finding is that people’s body, and specifically their self-perception of it as stigmatized, play an important role in the contextualization of the travel experience. The article concludes with managerial implications and suggestions for future research.