Glad to answer some of your questions.
1) You will probably want to just take a cab to your hotel (if it is somewhere downtown) from O'Hare. American Taxi or 303 Taxi is typically what I use, they have fairly decent rates. If you're flying in late at night there shouldnt be any traffic and it should be a fairly quick ride. You won't want to take the train at night, especially with luggage, etc.
2) I'm not sure on this, I would suggest just giving them a call on Thursday and asking.
3) The Loop/Grant Park area is kind of far from the airport, probably at least 30 minutes, most likely more if there is traffic (which there will be because they are still doing some construction on the expressways). But, if you're going to stay by the O'Hare area, you can take the train - specifically the Blue line of CTA - down to union station, which is right in the middle of downtown. From there you would probably want to take a cab to UIC.
Anyways, just some tips that you might want to look into - hopefully it helped!