Chicago is a swordsman for Freelancer, having always wanted to train to be like Agent Vermont. He is determined in honing his skills and creating a better future, having been living a life of uncertainty and fear of authority.

He often controls his fireteam when on the field and has an affinity for dramatics, seeing combat as like a dance. With the death of Agent Vermont, he used that opportunity to take up sword fighting to the extreme, throwing away his gun and now working entirely with his sword.