Many studies across disciplines assert that chronic illness and emotional wellbeing are closely related. Yet, studies in the literature rarely examined the mediators of the relationship from a socioeconomic perspective. In particular, despite its significance in the welfare of people in developing countries, studies have rarely investigated the effects of chronic illness on, among others, aspirations, the failure of which may be linked to a self-sustaining trap of poverty in developing countries. Using two waves of Indonesian Family Life Survey (IFLS 2007, 2014), this paper examines the effect of chronic illness on aspirations and the channel through which the duration of chronic illness affects aspirations and emotional wellbeing. To this end, this paper uses a variable measuring an aspirations gap, constructed by a difference between an individual’s current level of life evaluation and his/her future aspired level of wealth. Overall, results of this study suggest that chronic illness brings about a vicious cycle in which a deterioration in an individual’s current life evaluation, compared to the person’s cognitive neighborhood, leads to a greater aspirations gap, which, in turn, reinforces feelings of unhappiness and dissatisfaction with life. Furthermore, the effects of chronic illness are found to be greater on the poor in the bottom 25% of household income.