I know most guys look for a TS who is "functional", but I am looking for a more "feminine" experience.  Someone I can feel like they really are just a surgery away from being a woman - any suggestion in Chicago?

There are numerous very feminine girls in Chicago who while functional, can also provide what you're looking for. Alexa, Brasil, Maizza and Sissi are all gorgeous extremely passable girls who while functional can also provide the function you wish.