Very few people are "fine" being homeless anywhere and I don't think this is what OP was trying to say. But if you're choosing between being homeless in Chicago

Very few people are "fine" being homeless anywhere and I don't think this is what OP was trying to say. But if you're choosing between being homeless in Chicago and being homeless in LA or San Francisco, one of the options is much more attractive. There's a reason that newspapers in San Francisco don't have to report the number of people who froze to death each winter, which absolutely happens each year in Chicago.