i think jon is right, we need someone to at least oversee the hostel booking. i am assuming that we all want to stay in the same room again, and that needs to be arranged by one person to ensure that we book one whole room. many hostels have 10 or so beds in one room, if you book individually they just throw you in one. also some of the hostels in chicago are huge and will probably fill up fast, i think faster than the ones in toronto, so we will need to book very early, especially if we all want to stay together in one or two rooms. i think our best bet is the HI chicago hostel (
http://www.hostelworld.com/availability.php/HIChicago-Chicago-1853), since it is centrally located and has no curfew.
it would also help if we had a couple people to put together a few agendas for the trip, just so we all have a vague idea of what we are doing. we had a vague idea of what we were doing beforehand in tronno and that really helped to get everyone organized and together. even if it is as simple as on this day we will go to the aquarium, on this day we will go shopping on the magnificent mile, on this night we will invade joe hocking's place and have drunken acappella karaoke, etcetera it helps to have a plan.
carpools and rides and stuff.... that can be arranged on your own through PMs and such. but you should know that parking in chicago is a bitch, and not all hostels offer discounted parking, or parking at all. i see nothing on the HI chicago page about parking for cars, only for bicycles. in the past when i have stayed in chicago it cost between 30 and 40 dollars per day to keep my car parked in a garage, with no in and out priveleges so i couldn't even use the car at all. not like you need a car in chicago, but just something to keep in mind when planning your trip.