After living in there for four years, there are only two things that I have always wanted to do in Chicago and haven't done. One is to go out on a yacht, but that isn't going to happen until I make some rich friends.
The second is (was) to go kayaking on the Chicago River. I realize this sounds weird to people (well I only realize now because after telling a lot of people they thought it was strange), but I always saw the people in their kayaks when I walked over the river and it looked so cool. So I finally did it (and took Aaron along)!
I was nervous because I have never been in a kayak and am afraid of drowning, but it was easy and a ton of fun. It was awesome to see the buildings (especially the Trump Tower) from the river view. We didn't get any pictures because we didn't have a bag to keep our phones dry.
We also got to go to some of our favorite places, see some old friends, and even hit up the beach. And OF COURSE have a person asking for money on the street get aggressive when you don't give them any. Classic Chicago.
We stayed at this brand new hotel and it was kinda a little bit weird and high-tech/vintage (at the same time..), but a great location and a heavenly bed (I want to buy one).