I'm going to check out the Allerton, there is a suite offered as an option which would be appealing. We can make a standard room work, but we have three kids- 7,5, and 1.5 so bigger is always better!
I would love any insight you have to offer! We're planning on using public transit entirely so we don't have to bring car seats. On our to-see list is the Shedd Aquarium, Field Museum, Millennium Park/Maggie Daley park, and one of the observation decks. I'm thinking about buying the city pass ticket So I would say our 2 biggest priorities are location and size. On a superficial level though, I'd love a non-generic building... we're from Florida so most of our hotels are pretty standard buildings. I think my kids would be so wowed by a historic building!