Check out hotels.com for some good hotel rates. They will buttrape you on parking. Check out Groupon and Living Social since they offer getaways and hotel deals as well. I loved the Westin when I went. Walking the Mag Mile is always cool, you can take it down to Millenium Park to walk around there. I would suggest taking the water taxi up to chinatown and wondering around there. Go saturday or sunday for some Dim Sum for lunch. Most Ohians have no clue what this is, but just picture asian tapas. If you want to pull out all stops for something really special, take her to L2O for dinner. This is not cheap, the tasting menu was around $250-300 for both of us. This was a trip...the most memorable restaurant my fiancee and i have ever been too. Service is AMAZING...its like an orchestrated show, and the food was an artful experience. Definitely not for the faint of heart (or wallet) but if you wanted a one-off experience its great. Definitely something a lot of folks here would disagree with, but if your a foodie well worth it. Theres tons of good food around...cheap and expensive. The museum is tons of foun, check out the Museum of Science and Industry too. We've been several times and have yet to go see everything we wanted to see. I love Chicago.