Well I'd sure review the just-posted GNR winners and try to make sure I'd visited most of them at least once.
Then I'd also think about at least one of the ultra unique dining experiences like Alinea, Avenues, or Moto (or Trotters or Tru but as they are 'older' there's a good chance you've already done them).
I think Blackbird is a can't miss if you've never been there.
Honestly, though, the most fun one can have with food (at least with your clothes on) is at an LTHforum event. I'd say that, more than anything, is a "Don't leave Chicago without it" experience.
Care to share with us where your new home will be?
Objects in mirror appear to be losing.