In order to investigate the effects of filter length and ventilation on the transfer behavior of some ester flavors in cigarettes, the said ester flavors were injected into cigarettes with filters of various length and ventilation rates. These flavored cigarettes were stored airtightly for one week at temperature of 22°C±2°C and relative humidity of 60%±5%, then analyzed by simultaneous distillation and extraction combined with GC and GC/MS. The relationships of flavor transfer ratio with filter length and ventilation rate were studied by multivariate analysis and multi-factor interaction stepwise regression analysis. The results showed that: 1) The retention ratio in cut tobacco and transfer ratio into mainstream cigarette smoke of cinnamate flavors did not correlated with filter length and ventilation. 2) If the flavor’s physical properties were neglected, filter length would be significantly negatively correlative with flavor’s retention ratio in cut tobacco, but significantly positively correlative with flavor’s transfer ratio into filter. Filter ventilation insignificantly correlated with flavor’s retention ratio in cut tobacco, while it weakly positively correlated with the transfer ratio into filter. 3) The transfer ratios of ester flavors into mainstream cigarette smoke significantly negatively correlated with filter length and ventilation.