For future reference -
Things to do:
Magnificent Mile - awesome to walk and shop and feel the life/energy in this city.
Art Institute Museum - HUGE we spent almost 3 hours here did not see it all. I like how they don't give any "preference" to the major artists/painters. If you aren't paying attention you will walk right past Pollock, Van Gogh, Picasso, Monet, etc.
The bean/Millenium Park - you are right there, worth checking out for a minute.
Skydeck - skip this imo, see Signature comments below. Long line gets you to another room with a long line, to another room with a long line....
Architecture River Cruise - worth doing. Tons of great views and stories. Gets colder out on lake.
Eat:
Remington's - while you are at the museum/bean/Millenium Park, cool place to people watch and eat a good lunch.
Pizza - did both Giordanno and Lou Malnatti's. I don't get deep dish pizza so... whatever.
Nomi - eff this place. Had reservation for brunch, arrived with 2 open tables by window and we were told they were unavailable. Two couple's walked in behind us without reservation and were seated at those tables.

We left. Super stuck up uppity place anyway and we ended up at my favorite place we ate at the whole trip.....
Bar Siena - This place was great. Atmosphere great, food great, drinks great. Cool metal tree going up through both levels in the middle. Cool neighborhood. Get a Bombo.
Signature Room - From what I saw, I would make a reservation here. The tab will be relatively expensive, but you are going to pay $100 for these views at the skydeck (for 2 people). The food was OK and very generic. Was a great spot to watch the sunset and see the lights on go in the city.
Signature Room Lounge - apparently tourists use this to skip the price tag of the Skydeck. Wait in line for elevator ride, buy a $20 drink and see the views. Only problem is the place is a damned zoo. People almost wrestling to gets pics of the views, vultures trying to steal tables/chairs... not enough staff to keep order. Just spend the money and get a table in the restaurant below.
Chicago is a much cooler city than I had come to believe from brief work trips to the area.