My wife and I went last summer for our fifth anniversary. Loved everything about the city.
We went to APC the first night, got a seafood tower and couldn't handle ordering anything else. Included in the seafood tower were oysters, sea snails, crab, sea urchin, and tons of other sea faring goodies. A great way to start off our trip.
On our second night we hit up L'express. We were going for a classic french bistro feel and this place really did it for us. We started with a green salad(this was in July) and it was almost perfect. We then got a local mushroom on toast with a wine sauce. It blew us away. Steak fires were the main course and it was spot on. Wine prices were reasonable and service was excellent.
For dinner on our last night we went to Joe Beef. Walking in, the first thing we noticed was how homey it felt. Cramped almost. There were two rooms, and an outdoor patio(which looked amazing). We were seated in the room away from the bar where tables of two were crammed together. Really crammed together. We started with oysters, which were better than the best I've had in Chicago. I ordered the horse filet, which the kitchen cooked perfectly, but I wasn't too enthralled with. A little tough for my steak tastes. My wife ordered the rabbit sausage, but i couldn't even get a forkful because it disappeared so fast. You have no choice but to interact with the tables around you, which in our circumstance didn't work out so well.
I will be the first to admit that my reviews are being made through rose colored glasses. It was our anniversary trip and I have familial connections to the city. We didn't rent a car and either biked(much more bike friendly than Chicago) or took the public transportation for the whole trip. We hit up two outdoor markets(Jean-Tallon and Atwater) and were blown away by the abundance. The hardest part was leaving without trying so many other great places.
Geo's reviews were invaluable to us(sorry for not thanking earlier). Can't wait to get back.