Background: Chronic pain is a significant worldwide health problem. It has been reported that people with chronic pain experience decision-making impairments, but these findings have been based on conventional laboratory experiments to date. In such experiments, researchers have extensive control of conditions and can more precisely eliminate potential confounds. In contrast, there is much less known regarding how chronic pain affects decision-making captured via laboratory-in-the-field experiments. Although such settings can introduce more experimental uncertainty, collecting data in more ecologically valid contexts can better characterize the real-world impact of chronic pain. Objective: We aim to quantify decision-making differences between individuals with chronic pain and healthy controls in a laboratory-in-the-field environment by taking advantage of internet technologies and social media. Methods: A cross-sectional design with independent groups was used. A convenience sample of 45 participants was recruited through social media: 20 (44%) participants who self-reported living with chronic pain, and 25 (56%) people with no pain or who were living with pain for <6 months acting as controls. All participants completed a self-report questionnaire assessing their pain experiences and a neuropsychological task measuring their decision-making (ie, the Iowa Gambling Task) in their web browser at a time and location of their choice without supervision. Results: Standard behavioral analysis revealed no differences in learning strategies between the 2 groups, although qualitative differences could be observed in the learning curves. However, computational modeling revealed that individuals with chronic pain were quicker to update their behavior than healthy controls, which reflected their increased learning rate (95% highest–posterior-density interval [HDI] 0.66-0.99) when fitted to the Values-Plus-Perseverance model. This result was further validated and extended on the Outcome-Representation Learning model as higher differences (95% HDI 0.16-0.47) between the reward and punishment learning rates were observed when fitted to this model, indicating that individuals with chronic pain were more sensitive to rewards. It was also found that they were less persistent in their choices during the Iowa Gambling Task compared with controls, a fact reflected by their decreased outcome perseverance (95% HDI −4.38 to −0.21) when fitted using the Outcome-Representation Learning model. Moreover, correlation analysis revealed that the estimated parameters had predictive value for the self-reported pain experiences, suggesting that the altered cognitive parameters could be potential candidates for inclusion in chronic pain assessments. Conclusions: We found that individuals with chronic pain were more driven by rewards and less consistent when making decisions in our laboratory-in-the-field experiment. In this case study, it was demonstrated that, compared with standard statistical