This study explored the effect of situational factors on pedestrian intention to jaywalk. In particular, eight scenarios were designed to manipulate three situational factors, namely, time pressure, descriptive norm, and official supervision. A total of 124 subjects participated in the study. Repeated-measures ANOVA analyses indicated that hypothetical high time pressure, negative (unsafe) descriptive norm, and unsupervised effect significantly increase pedestrian intention to jaywalk. Additionally, the effect of descriptive norm was moderated by official supervision, which implied that only under an unsupervised condition can descriptive norm serve an important function in predicting pedestrian intention to jaywalk. The potential implications of this research were discussed.