My wife and I spent an early 6 month anniversary in Chicago. I hadn't been since I was a child and my wife had never been. We found some cheap airline tickets but quickly saw that hotels are quite expensive in the heart of Chicago on a weekend. We decided to try Priceline's "Name Your Own Price" hotel feature and it worked out nicely. It gives you the option to choose different tiers of hotels and gives you a comparison to what your hotel will be similar to so you don't have to go in completely blind. The hotel we got was right on the Magnificent Mile so it was perfect for our short 4 day weekend. We saw as much as we could and really hit the ground running! The scale of the skyscrapers is something that you need to experience in person. You simply can't capture the magnitude with a camera. That was my biggest takeaway photographically! The dramatic setting of the skyscrapers overlooking the skyline and Lake Michigan was absolutely inspiring. Mix in some upscale shopping, deep dish pizza, coffee on the 95th floor of the John Hancock Building, standing on "The Ledge" at the Willis Tower (formerly Sears Tower), spending an afternoon at the Science and Industry Museum, walking around Millennium Park and along the Chicago River, and stopping by the zoo before seeing the best comedy and improv we've ever seen at Second City made our weekend a blast! It was also special to be able to ride the Navy Pier carousel the day before it was knocked down to build a new-and-improved model. Next time we will plan to go to the top of the John Hancock or Willis Tower again because we were told that (on a clear day!) you can see 4 states but unfortunately it was too foggy during our trip.