This paper describes the simulation, fabrication and characterization of silicon-based rectangular hollow waveguides. Numerical evaluation of such structures has been done using both modal propagation and ray tracing, low total losses and multimodal behavior, even for small core sizes, are predicted. Since light propagation in rectangular hollow waveguides strongly depends on the Fresnel coefficients at the facets, the technological processes have been optimized to obtain wall angles close to 89° and wall and base average roughness of 57 nm and <5 nm, respectively. Hence, roughness is negligible to the working wavelength (678 nm). Measured waveguides show total losses close to 6.0 dB for 3.0 cm length. The non-lineal response due to mode filtering in hollow waveguides has also been experimentally observed. Finally, loss simulations and measurements are in agreement, especially for the widest waveguides. For thinner structures, the reduction of the depth due to the DRIE process, together with the blundering of the vertices, causes a dramatic attenuation increase. All these effects should be taken into consideration when defining hollow structures.