Nonlinear optical phenomena in silicon such as self-focusing and multi-photon absorption are strongly dependent on the wavelength, energy, and duration of the exciting pulse, especially for wavelengths > 2 µ m . We investigate the sub-surface modification of silicon using ultra-short pulsed lasers at wavelengths in the range of 1950–2400 nm, at a pulse duration between 2 and 10 ps and pulse energy varying from 1 µJ to 1 mJ. We perform numerical simulations and experiments using fiber-based lasers built in-house that operate in this wavelength range for the surface and sub-surface processing of Si-wafers. The results are compared to the literature data at 1550 nm. Due to a dip in the nonlinear absorption spectrum and a peak in the spectrum of the third-order nonlinearity, the wavelengths between 2000 and 2200 nm prove to be more favorable for creating sub-surface modifications in silicon. This is the case even though those wavelengths do not allow as tight focusing as those at 1550 nm. This is compensated for by an increased self-focusing due to the nonlinear Kerr-effect around 2100 nm at high light intensities, characteristic for ultra-short pulses.