We experimentally investigated the impact of rooftop stack position on the pollutant entrapment within 2D street canyon configurations. Analyses were performed in a water channel loop system by using the image analysis techniques: FTV (Feature Tracking Velocimetry) and LIF (Light Induced Fluorescein) respectively for measuring velocity and concentration. The set-up consists in an array of 20 identical buildings with aspect ratio equal to one (ARB = B/H, where H is the height of the eaves and B is the building width), mimicking an idealized 2D urban canopy. They were equally spaced with a unitary canyon aspect ratio (defined as ARC = W/H; where W is the distance between buildings facades), and varied in shape by using flat and gable roofs with pitch α = 45°, with different chimney positions and heights, for a total number of 9 investigated configurations. Results demonstrate that the presence of gable roof significantly varies the flow in the shear layer, which, in combination with different chimney position and height, lead to not trivial effects on pollutants dispersion.