I grew up in Chicago, and am just returning to the city after 2 years in DC and 3 years in Boston. People in Boston often asked me to compare the city to Chicago, and I staunchly maintained the position that Chicago was superior in all ways. However, there seemed to be far more "casual fine dining" restaurants in Boston (well, in Cambridge, actually) than in Chicago. I did some searches and found the discussion where an SF hound contended that the same was true of San Francisco, and having spent a summer there, I tend to agree.
While I know "casual fine dining" means different things to different people, here's what I'm looking for: a restaurant with excellent food with entrees in the $20s (if one steak/lobster/other luxury entree is in the $30s, that's fine). It can be any cuisine; however, I'm not looking for recommendations for Khan BBQ, Spoon Thai, Xni-Pec, or other inexpensive holes-in-the-wall. While I love those places (I made a point to keep up with the cuisine here on my visits home!), they don't have the atmosphere that one is sometimes looking for when it's not really a special occasion, but you want to dress up a bit and have a "date night."
If any hounds are familiar with Boston, something like EVOO would be perfect; Rendezvous, Blue Room, Green Street, and (sort of) West Side Lounge would also fit the bill. It really does seem that most of the Chicago restaurants mentioned when people make requests like this have entrees in the $30s. Thus far, according to online menus, Sweets & Savories, May Street Market, and Lula Cafe fit the bill. Any other thoughts?