I read somewhere, I can't remember where, that there are only 3 easily-distinguishable skyline in the US (or was it North America...): San Francisco, New York, and Chicago.
I am so happy to say that I visited two and I now live in one. And, I might be biased here, but I think Chicago has the best one... :)
These photos were taken while the wife and I were aboard the Sea Dog Extreme Thrill ride. (I reviewed the Think Tank Photo Urban Disguise 35 V2.0 during the ride also.) Catch that ride while you still can this year. And if you can't make it and if you'll be in Chicago next summer, I suggest you take that ride. Just be prepared to get soaking wet!
Gear used to make this post: