River floodplains in the Netherlands serve as water storage areas, while they also have the function of nature rehabilitation areas. Floodplain vegetation is therefore subject to natural processes of vegetation succession. At the same time, vegetation encroachment obstructs the water flow into the floodplains and increases the flood risk for the hinterland. Spaceborne pointable imaging spectroscopy has the potential to quantify vegetation density on the basis of leaf area index (LAI) from a desired view zenith angle. In this respect, hyperspectral pointable CHRIS data were linked to the ray tracing canopy reflectance model FLIGHT to retrieve vegetation density estimates over a heterogeneous river floodplain. FLIGHT enables simulating top-of-canopy reflectance of vegetated surfaces either in turbid (e.g., grasslands) or in 3D (e.g., forests) mode. By inverting FLIGHT against CHRIS data, LAI was computed for three main classified vegetation types, ‘herbaceous’, ‘shrubs’ and ‘forest’, and for the CHRIS view zenith angles in nadir, backward (−36°) and forward (+36°) scatter direction. The −36° direction showed most LAI variability within the vegetation types and was best validated, closely followed by the nadir direction. The +36° direction led to poorest LAI retrievals. The class-based inversion process has been implemented into a GUI toolbox which would enable the river manager to generate LAI maps in a semiautomatic way.