I could have picked a better day for this, but here goes anyway. Having poked the mods about a possible plot, I'm here to see what could be worked out with the characters.
I'm thinking of bringing in this girl as an envoy from another mafia family, operating in another city. Considering that the Chicago market is becoming a little crowded, perhaps one or two or all the families might be interested in projecting their influence outward. Certainly, if any of the characters would like to travel outside of Chicago, it might be nice to have some security that they won't be gunned down in the street. (Or that they can count on a third party to gun down the other family's traveling agents without any cost to them.)
My question to you is which one of the families would be interested in this idea more so I can figure out how to place her in the game and where she would stand in relation to the others. Her power vis-a-vis the families would be negligible, perhaps with the single caveat that she represents another power structure and getting through to the people behind her could yield some considerable profit for those concerned.