I would probably take the South Shore train to Chicago from Hammond so I don't have to deal with the traffic. Hammond would be a great second choice, but it is bit too far out of the city.
I am very interested in the south branch of the river and a spot at River City for several reasons. The water in that part of the river is warmer than the lake(the ice starts to melt at Jackson street). I work at Adams and Canal so it is close to my work and gym. Lastly, living in the heart of the city would allow me to get rid of my car.
Once I get this all figured out I am going to put up a website so others can join in the fun!!