For food, it really is up in the air on budget. The best place in town is Capital Grill, but its about 50+ for a dinner entre. The place I would recommend would be Mason Street Grill. They have the best steaks in my opinion, however they can get pricey from 30-40 for a steak dinner. They do have cheaper food as well, there menu's on the website have prices.
Bar Wise:
Without knowing the kind of people you are bringing out, I couldn't tell you the best place. But if you narrow it down to an area, I can give you what each bar brings. 99% of all the bars allow smoking still, we are not smoke free until next year.
There are 3-4 major areas you could go and be able to walk to multiple places. First one is Water Street. Water Street does have more 21-27 yr olds. It does have a few good places, McGillycuddy's, Bar Louie (This is a chain).
Second area would be North Avenue, slightly older crowd but still attracts some college kids. Again, this area has 10-12 bars, some bad, some decent. But enough to get you stumbling.
Third area would be the Third Ward. This is a newly renovated are with alot of different kinds of bars. The one I enjoy would be the Milwaukee Ale House, they brew there own beer and usually have live music. Depends on the night, but mainly a crowd from 25-35 after 8pm. They do have a nice restaurant during dinner hours as well.
More info on the type of people, the better idea I can give you of where to go.