It's been 5 years or so since I lived there, so I would double check my information before making a final plan.
For a nice ambiance and good food, I would go to Water Buffalo in the Third Ward, it's on Water street and Buffalo I think.
My wife and I used to love going to Water Street Brewery for the hot bacon spinach salad and the pretzels.
It may be too late in the year, but Lakefront Brewery used to have fish frys on Fridays which were a blast, very fun experience.
And since no one else has said it, try Sanford restaurant in the lower east side. It is the best place in Milwaukee and a top restaurant in the country. It's small and expensive, but it is probably top 3 restaurant I have eaten at in my life. Apparently it was sold to the head chef since I have been, but people seem to say the food has not changed. To top it off, they have apparently partnered with a brewery and have some exclusive beers, so that would be worth it alone in my opinion. Last I went, I had a cup of coffee that was hand blended and roasted by the chef. It was so good I am posting about it here. I can only imagine his beer would be just as good.