The acoustic environment in urban open spaces has played a key role for users. This study analyzed the different effects of contextual factors, including shop openness, season, and commercial function, on the soundscape in two typical commercial pedestrian streets. The following observations were based on a series of measurements, including crowd measurements, acoustic environment measurements, and a questionnaire survey. First, the number of talkers in Central Avenue was greater than the number of talkers in Kuan Alley in cases with the same crowd density, while there was no significant difference in the sound pressure level. When the crowd density increased, acoustic comfort trended downward in Kuan Alley, while the value of acoustic comfort in Central Avenue took a parabolic shape. Second, there was no significant difference between the number of talkers in summer and the number of talkers in winter; however, when crowd density increased by 0.1 persons/m2, the level of sound pressure increased by 1.3 dBA in winter and 2.2 dBA in summer. Acoustic comfort took a parabolic shape that first increased and then decreased in both winter and summer. Regarding commercial function, as the crowd density increased, the number of talkers and the level of sound pressure both increased, while acoustic comfort decreased in three zones with different commercial functions. In addition, a cross-tab analysis was used to discuss the relationship between the number of talkers and the level of sound pressure, and it was found to be positive.