The synthesis of unsaturated polyamides that can be obtained from plant oil derivatives via two different approaches is described. First, long chain aliphatic α,ω-dienes with two symmetrically spaced amide segments were polymerized via ADMET polymerization. Secondly, dimethyl(E)-icos-10-enedioate, a bio-based unsaturated monomer that was obtained via metathesis, was polymerized with different aliphatic diamines using strong organic bases, such as TBD, as catalysts. Both reaction pathways led to unsaturated PA X,20 and the two different routes were investigated, optimized and compared. Moreover, the polymers were characterized by 1H NMR analysis and SEC, and the properties of the resulting polyamides were investigated by DSC and TGA.