Top of hancock tower, top of Sears tower, Michigan Ave. shopping, water tower place, the Frank Lloyd Wright neighborhood tours, Greek Town, etc.
Hotels are pretty straight forward, the higher the price the better the location. I have stayed at the Palmer House and the Drake many, many times and would recommend both highly. There is a brand new Hyatt at water tower place that is right in the middle of it all. Any good guide book, or search of chicago museums is gonna kick out all the majors and a few of the minors. There are also tours that go along with famous movies shot in chicago, the Ferris Buller tour, the Blues Brothers tour, etc. large malls in the sub urbs, woodfield was the largest mall in the US until Mall of America was built. There is an Ikea out there as well.