chicago squatting

Look for foreclosed homes, in Chicago. Some might be winterized so no water but, the electric should still work. Breaking in is a piece of cake and most of the time if you lay low keep it all back door you can go unnoticed by neighbors. As for the banks they don't give a shit about the property so nobody is going to bother you.
 
South Side Chicago, no exaggeration about 1/4 of the homes are foreclosed and sitting empty and boarded up. Every block has at least 2.
 
search foreclosure properties, scout 'em out for a few days, see which one is most accessible, low key, etc. As far as electricity goes some firms leave it on some don't. I wouldn't suggest rigging it if you don't know what you are doing and here you can get serious jail if you jump the meter and they find you. I am pretty sure almost every foreclosure in CHI would be winterized but, that is good that means they probably are going to be empty for a while, if you are looking long term. Be careful squatting the apartment blocks as investors often snoop around those areas. If you are concerned about keeping warm, if I can find it I had an old how-to on rigging space heaters to batteries. I'll look around.