Thanks for the feedback. River City is privately owned now so you can't rent there in the summer. In the winter, when most people pull their boats, a slip there is pretty reasonable. You just need to connect with one of the slip owners. I want to be in Belmont or Diversey in the summer months. Due to the draw bridge situation, keeping a sailboat on the river in the summer is not possible.
As far as the cold, I am am from northern Minnesota, so Chicago isn't that cold. It's all relative I guess. The river is warm south of Jackson and never gets ice. There is some kind of plant there that dumps warm water into the river. In the winter I can actually see the ice start to melt at Adams St. from my office window. With the proper insulation and heat set up, I am sure I could be comfortable. Besides, It is really only cold here from mid December to the end of March.
I plan to take the stick down in he fall so I can get off the river at my convenience. Getting early arrival and late leaver permits from the city should make the transition back and forth to the lake a snap.
Have a good trip down.