I'd like to keep it under $200 after drinks, food, and tip. Good food is worth it to me, and I only see my fiance ~4 days a month, so I splurge for her.
Oh damn then. lol. Well here come my foodie recs then:
Goosefoot JUST opened a month or two ago, and has been getting INCREDIBLE buzz, and is only going to get busier... so getting in now might be a good idea. The chef is Chris Nugent from Les Nomades who wanted to branch out. 90 dollars for an 8 courser, but it's BYO. I'm going next week myself.
Slurping Turtle is great for noodles and opened recently, but probably less romantic, and can get pretty busy.
Also Acadia is a new restaurant that's down in my neighborhood in the South Loop area. It's pretty good... Entrees will run you about 30 or so.
Also I have to put a plug in for Ruxbin... Korean food but made in a traditional french cooking method.
Of course there's a ton of standbys... Girl and the Goat, Frontera, etc.
Hope that helps some. Feel free to PM me for more... I try to stay pretty plugged into the food scene, and go out to eat way more then I probably should.