Chasing, or continuing to gamble to recoup losses, is a behavioral marker and a diagnostic criterion for gambling disorder. Research on chasing has focused mainly on adults, whereas the analysis of chasing behavior among adolescents has not received empirical attention in the gambling literature. The aim of the present study was to first investigate the interplay between chasing behavior, craving, temporal perspective, alcohol use, and gambling severity among Italian adolescents. Three hundred and sixty-four adolescents took part in the study. Participants completed the South Oaks Gambling Screen Revised for Adolescents (SOGS-RA), the Gambling Craving Scale (GACS), the 14-item Consideration of Future Consequences scale (CFC-14), the Alcohol Use Disorders Identification Test (AUDIT), and performed a computerized task assessing chasing behavior. Participants were randomly assigned to the control and the loss condition of the computerized task. Results indicated that the choice to continue playing, as well as chasing frequency did not vary as a function of experimental condition. Hierarchical logistic and linear regression analyses revealed that the decision to chase depended mostly on craving, whereas chasing propensity was affected by craving and alcohol misuse. Notably, gambling severity did not predict either the decision to chase, or the chasing persistence. The present study contributes important findings to the gambling literature, highlighting the role of craving alcohol use in facilitating the inability to stop within-sessions gambling among adolescents. These findings may provide evidence that nonchasers and chasers represent two different types of gamblers, and that the difference may be useful for targeting more effective therapies.