Without knowing your actual budget and what kind of hotels you prefer (chains vs. boutiques, big vs. small, etc.), it's kind of hard to offer anything more than personal preferences. My preferences for that general area: 1) Dana Hotel and Spa; and 2) Sofitel.

Same goes for recommending restuarants in that it would help to know what kinds of food you'd be up for trying.

As for Friday afternoons in the Summer, I'd suggest having lunch in Millenium Park...it's also a good place for having a few drinks too. A walk along the Lakefront is always great. You can also rent a bike at the north end of Millenium Park and ride the Lakefront too.

And don't forget to extend your trip to Sunday.