Two enantiomeric amphiphiles containing the stilbene moiety (L-StG and D-StG) were assembled into ordered Langmuir-Schaefer (LS) films through the air/water interface and their circularly polarized luminescence (CPL) was investigated. When the molecules were spread at the air/water interface, a monolayer with nanofiber structures was formed, which could be subsequently transferred onto solid substrates by the LS method. The LS films showed both circular dichroism (CD) and CPL, whose handedness was determined by the molecular chirality of the amphiphiles. When the amphiphilic molecules were spread on the aqueous subphases containing cyclodextrins (including alpha-CyD, beta-CyD, or gamma-CyD), similar nanofiber-featured films were formed. However, the CD and CPL showed different changes. When L-StG was spread on the cyclodextrins, both CD and CPL were enhanced. When D-StG was reacted with cyclodextrins, the CD signal decreased while the CPL was enhanced. It was suggested that the chirality cooperation and conflict between the point chirality from the amphiphilic stilbene and the cavity chirality of cyclodextrin led to the phenomenon. However, in any case, the immobilization of the stilbene by the cyclodextrins caused the enhancement of CPL.