It seems to me what will be most desired is
Would the best thing we can do be to get a room with a comfy bed, room service, and wifi? Or are they so used to no sleep that it's no longer a priority? He's not 21 so going to a bar is a no-go, and he has no gf/wife so certain *other* activities are not something we need to worry about on this trip. :)
My son wanted to tour Chicago since he had never been. We did Navy Pier, Wrigley Field and the Sears Tower. He said he joined the Navy to see the world. We were lucky though because he didnt leave til Sunday night so we got 3 full days with him. He then went to A school in Pensacola and is now in Virginia Beach. Loving every minute of it.