I have a student who really wants to do his night cross country into Chicago O'hare. I was wondering if anyone has any experience/advice for flying into ORD in something like a 172 or Archer. Will they let you do a touch n go lol? Do you think it is worth calling the tower by phone and asking them a good day/time? We were thinking that if we made the attempt we would probably try it late at night probably after midnight.

To give you some background, my student has been flying for a couple years and is a sport pilot with over 100 hours, upgrading his cert to private. He's been renting planes out of a Class C airport, so I know he has some experience dealing with ATC and has been around the block more than the typical private pilot student.

I've flown into Bravos a handful of times, and am up for a challenge, but I'm also a pretty new instructor and do not want to put myself in a bad situation. I figure if I can't find someone who has some experience flying a training plane into ORD (or somewhere equally as busy) to give me some advice, I will offer to take my student to STL or Midway because I've flown 172's into both and I know they will deal with small GA.