I wouldn't imagine that there was a topic covering "my" vacation to Chicago but rather vacations in general.
That being said I just wanted to point out some of the more interesting locations.
For example the museums I visited
Science and Industry: a lot of the areas were customized for children and or under construction. My kids enjoyed the experience particularly a theatrical production called "Poop Happens" They also had a decent flight simulator of the F-35 where you get to go a blow up an enemy base.
Field Museum: was more of a contemporary museum geared towards adults curious about histories both ancient and recent. Egypt, Africa, Americas, and Societies to mention a few of the exhibits I particularly enjoyed the Reconstruction of an Egyptian Temple (don't recommend if your claustiphobic).
We also went to the Sears tower to the observation deck. I was surprised we were that lucky; we happened to arrive on a clear night just as the sun was going down most probably moments before the street lights came on. We could actually see all the way in to Indiana across Lake Michigan. If you like (as my wife says) "all the pretty lights" of "Kriss My Ass" (Christmas) you'll thoughly enjoy the view at night.
Shamburg Mall: This is a big mall by all means I am just not much of a shopper. I'll try not to be bias. The mall is filled with women’s clothing stores. They have build a bear, friend, and ride (cars/remote) they also have your hot topic and torrid, along with Spencers. They have dinning from $5 USD to $50 USD depending on your preferences. Additionally they have various electronic stores. They have at least two gaming shops one in to game consuls and the other was all "War hammer 4000" (a large scale dice game).
Now you must understand that Chicago and surrounding area is much larger than I could have experienced in 2 days but I found it enriching and challenging. If you happen to go on vacation please feel free to write about it here and share your thoughts.