I live about 3 blocks from the Drake. Several of the rec's here are very good, but if you still don't have plans I'll narrow it down a bit and add at least one.
Naha is awesome. Different preps, great wine list (though the markup is above average). I don't think it's terribly over- or under-priced for its peer group. But the room is LOUD. REALLY LOUD.
Cafe Spiaggia is great food, but in my opinion just isn't special. Especially for a "night in the city".
North Pond is totally awesome. Great food, beautiful room, and a lovely setting. You probably don't want to walk there, unless you don't mind showing up rather shiny. However, walking home through the park might be possible (you're looking at probably 1.5 miles though).
No offense to anyone, but Roy's, Cape Cod Room, and Hugo's/Gibson's don't really keep up with the rest of the group for food.
Drawing Room is a super-cool place for a drink, and a small plate might catch your eye.
Cafe des Architectes is a really neat place, and Noguier's food can be fantastic, but I continue to think the front of the house needs work.
Unfortunately I've still not made it to Merlo or Pane Caldo, so can't comment. Come to think of it, that sounds kinda good.

My wife and I really like Eve on Wabash. Small and beautiful room, nice food, great vibe.
Another interesting choice is Balsan at The Elysian. Bistro/gastropub style food, very chic/modern/"big city" vibe. Rather loud and scene-y though.
Eve
840 N. Wabash Ave.
Chicago, IL 60611
312-266-3383
Balsan
11 E. Walton St.
Chicago, IL 60611
312-646-1400