Hey Super -
There's a H&M right across the street from Water Tower Place on Michigan Ave. Also, if you'll be doing shopping on State street, there is Forever 21.
Instead of going to the Sears, just go up to the Sky Lounge in the John Hancock. It's a great view and it's free! The drinks are expensive, but if you just want to check out the view, it's a great alternative to the Sears and it's right on Michigan Ave.
If you want to hit some boutiques, the neighborhoods are where you'll want to be. I live in Roscoe Village and there are some great shops around my place. Most are quite pricey, but Hanger 18 on Roscoe and She One on Southport are reasonable and they have great clothes & jewelry. Plus, both neighborhoods are easily accessible on the L. Are you coming into town solo? with friends?