The last few times we've been to Chi-Town, we've done the typical tourist thing - just took the train in or drove and parked in a Spot-Hero lot for the weekend while we stayed in a hotel downtown. We go for the ethnic food and/or to hit our favorite blues club up in Wrigleyville. It's always fun in a "breakfast somehow cost $50" sort of way.
This is just the normal big city fleecing, and it doesn't hold a candle to the costs in say, Vancouver.
What I'm complaining about is what was occurring when my daughter lived in "real Chicago", out in the neighborhoods. There are no day-rate lots - just on-street parking or permit lots. The frustration was that it's actually cheaper and easier to park at a lot inside the Loop than to find a spot in Wicker Park or Boys Town. Compounding that is that the vehicle needs to be moved regularly, or it'll get towed. The net/net is that visiting friends or family who live in an apartment with no off-street parking out in the neighborhoods is nothing at all like going to a trade show at McCormick Place and staying at a hotel on Michigan Ave.
People shoot each other over parking places in the tougher parts of town (which is everywhere), and the cops are more interested in ascertaining if your car hasn't moved in 24 hrs than if you had to shoot at somebody to get the spot in the first place.