Here's how it happened:
First off, it was not a complete surprise. We got the ring ordered together, and Tracy knew she had to 1) dress up and 2) have a bag packed that morning that I could take.
That being said, I had made reservations at the Signature Room for the meal. It was a bit of no brainer, as she had never been there, and really, it's on the 95th floor. It's pretty cool. I wanted something memorable, and that fit the bill nicely. I has some help setting up the details from one of the people where we got the ring from. (Robbins Brothers. I'll pimp them to anybody who will listen, I think they did a great job across the board.) Anyway, we set it up for a window view, for obvious reasons, and warned them that I would be proposing, and that there would be props. Then I reserved a king suite with a jacuzzi tub at the Hotel Allegro.
That morning, I took our bags, a couple of bottles of wine, and some snacks down to the hotel and checked in. Basically, just to get the room ready, I put the chocolates on the bed, and chilled the wine. When I was checking in they asked if I was down there for anything special, so I told them and the concierge told me that he'd have a bottle of champagne chilled in the room for when we got back. I didn't have the heart to tell him I already had a bottle, plus, I like getting free stuff. Then I headed back to my place to get changed and ready. This part became a little dicey because, for anybody who was in Chicago at the time knows, it was snowing. The roads were ugly, but fortunately, traffic actually wasn't too bad.
I went and picked up Tracy. I found out at this point that she had a surprise for me, which was basically that since I wasn't telling her where we were going, she wasn't going to show me what she was wearing (the answer wasn't nothing. It was cold outside and that sort of attire isn't really appropriate for upscale dining). We get into the car, dressed up and bundled in long coats, and headed downtown.
While I hadn't told her where we were going, it became pretty evident as we headed into the parking garage for the Hancock Building, and made our way up to the restaurant. As I mentioned, the weather was crappy all day, snow and fog, but by the time we got there it had actually cleared up nicely. We had a great view of the ground and off into the distance, plus, little cloudy kept floating by. It's impressive seeing the city like that, like dining while landing on a plane. You're so high up that the lights of the city seem to go on forever.
We got a glass of wine, Grilled Prosciutto and Buffalo Mozzarella for an appetizer, and Tracy got crab legs while I went with the roast duck.
After dinner, I had arranged for the server to bring in two fortune cookies on a platter. Tracy opened one, which said "Will you marry me". I got down on my knee and asked her if she would share all of the fortunes with me and if she would marry me.
It's a good thing she said yes :-) And the people around us gave us a round of applause, so hopefully they weren't too distracted by what we were doing. Even before that, we were being pretty touristy, taking pictures and looking at everything.
Several minutes later, the server came by with glasses of champagne that had strawberries with candles in them on a tray saying congratulations.
After diner, we went back to the hotel and relaxed the rest of the evening.
And some pictures (via snapfish, so let me know if there's a problem)
That's how it happened. Everything worked out great. :-)