There are plenty of hotels in downtown Chicago, but they are certainly pricey, especially for the weekends. Parking is usually around $30/day, too. As far as transportation goes, you can walk from any point downtown to another. Cabs, buses and trains are also easily available at all hours.

More importantly, anyone want to make a suggestion where to socialize Saturday night? I'm willing to get out my Chicago dive bar book if need be, but I know a few dozen decent places within a two mile radius of downtown.