I hate to say this but... "Welcome to Chicago". I know that Aaron and others will disagree. I would LOVE to know where you live! I moved here from Florida, and it has been nothing but misery and torture when it comes to "hospitality" in Chicago. Maybe I am just unlucky, but in all honesty, it's nice to hear of someone else having trouble. I thought I was losing my mind until last month when I was fortunate enough to vacation in Florida. Then I was reminded of the truly "first class" world. And it's not just at the 5 star resorts, but at the holes in the wall, they treat you well. Again... "welcome" to Chicago... good luck finding that here. As far as deals in downtown Chicago, I don't really know of much. I am curious as to why you will have a car in Chicago. Are you driving here? Are you renting a car from the airport (please don't)? Don't rent a car. You are here for a convention? Why can't you stay outside of the city and take the Metra in? But then again, you mention you will be traveling with children. What do you plan on doing with your children when you are at a convention? If you are flying in here, don't rent a car, you don't need it. The public transportation from Ohare and Midway are fine. And once you are in the city, you would absolutely hate having a car, it's completely worthless. You are staying at a 4+* hotel, make the concierge earn their salary. Ask them how to get from point A to B. Then ask the bum outside of the hotel for good advice (give him a dollar or two and get the RIGHT answer). You'd be surprised. Oh, I feel for you. Again, the others would disagree. But from your statements, it sounds like you come from a friendly State. Please be aware that the sales tax in Chicago is absolutely ridiculous. 12 or so percent. Unless you like paying 7 dollars for a hot dog that is ruined with pickles and tomato slices on top of it, with the ridiculous poppy seeds, it will not be worth your money to eat in the city (let the flame wars begin!)... it's just not worth it. Take care, Miss Poofy :)