This study investigates the effects of individual traits and products characteristics on customer evaluation of sweepstakes promoted by retail firms. We assume that customer’s preference toward sweepstakes is determined by four primary attributes: implementation term, entry condition, prize size, and winning odds. The importance customers attach to these attributes are proposed to be influenced by the extent of rationality, regret, and store loyalty. Further, we explore how the evaluations are moderated by the type of product category (goods vs. service) and product involvement (low vs. high). The results from a conjoint analysis and a multivariate regression analysis applied to ordered-preference data show that rationality and behavioral loyalty have significant effects on the importance attached to implementation term, prize size, and winning odds. Further, the results also reveal that attitudinal loyalty play a significant role in the evaluation of low involvement products, while rationality and behavioral loyalty appear to be influential for high involvement products. These results provide new insights into the interplays among sweepstakes attributes, individual traits, and products characteristics as well as managerial implications for retailers developing a loyalty program strategy.