To those that care, I'm following up on my Chicago trip that so many graciously offered advice for http://www.elevenwarriors.com/forum/anything-else/2014/05/35801/calling-all-chicagoans
My wife and I drove to the South Side Line stop in Indiana and rode the train into the city from there. Free parking at the train station as opposed to parking downtown or doing the valet at the hotel. We got off at Millenium Park stop two blocks from our hotel. We got upgraded at the hotel to the 12th floor, corner suite over looking the river. It was fantastic. We took the boat tour on Friday which was fun to learn about all the buildings and the history of the river/city. We did a pub for dinner just around the corner from our hotel to watch World Cup games.
Saturday we shopped and did the big fancy dinner. We started out by going up to the Signature Lounge at the Hancock Tower, getting the $15 cocktails to take in the view. We ended up choosing Benny's Chop House for dinner and it was a great choice. Amazing service, they gave us a menu with Happy Anniversary printed on it, the entire staff congratulated us on our anniversary, and our waiter ended up ordering us a dessert. It was the S'more Cheesecake which is not something I would have ordered but now that I've had it, I wouldn't order anything else. My steak was of course perfect in every way. We got a nice Riesling which the sommelier actually complimented us on saying it goes better with steak than red wine and no one will ever tell you that because it's cheaper and they want you to order expensive red wines. It was pricey, but we really enjoyed every minute of it.
Thank you all for all your suggestions as I did get a lot of good tips and leads from all the comments on here.