Jason and I got on this topic the other night at dinner, so I thought I would post our list of Chicago favorites.
1. North Pond
There's just something special about North Pond. It's in the middle of Lincoln Park (the actual park!), the food is unbelievable and fresh, they use mostly local/seasonal ingredients, and the service is impeccable. It also helped that we knew one of the sous chefs when we went so we got a couple of fun extras (free champagne, recommendations, dessert, etc). I remember having a black sea bass dish and thinking at the time it was the best piece of fish I ever had. We only ate here once, about 5 years ago, but it still stands out as my favorite dinner in Chicago.
http://chicago.metromix.com/restaurants/contemporary/north-pond-lincoln-park/134922/content2. Blackbird
We went here to celebrate when Jason got his job offer at MedPage (little did we know there was nothing much to celebrate!) and just sat up at the bar to eat. It's kind of a fun way to do fine dining. We chatted with the bartender and got some good Chicago foodie gossip, ordered whatever he recommended, and loved every bite that went into our mouths. Some of the combinations sound a little strange on paper, but you have to trust the chef. Everything on that menu works!
http://chicago.metromix.com/restaurants/contemporary/blackbird-west-loop/135951/content3. Japonais
While North Pond and Blackbird are both really great date night restaurants, Japonais is hands down the best place in Chicago to go with a group (assuming everyone is willing to lay down $100 each for dinner). It's got a really cool vibe going and everything on the menu is delicious. I love the Kobe beef carpaccio, and there's also some kind of steamed sea bass dish (can you tell I like sea bass?) that comes in a bag of the best-smelling broth...I wanted to put my face above the plate and just breathe. Heaven.
http://chicago.metromix.com/restaurants/international_fusion/japonais-river-north/144700/content4. Marai
Ha, I didn't realize one of the owners of Japonais is also the owner of Marai until I went on Metromix to copy the links for this post... Makes sense that I love both restaurants! Anyway, I think I have a soft spot for Marai because it was the first time I had really high-quality sushi and learned about the magical goodness of fatty tuna. They have a special king crab roll that is to die for, but watch out because it's hot (temperature-wise). I burned my tongue once.
http://chicago.metromix.com/restaurants/international_fusion/mirai-east-village-ukrainian-village/142864/content5. Meritage
I can't post a link for Meritage because it's gone :(. There's a new restaurant, Duchamp, in its place, but it just doesn't compare. I miss Meritage, especially for it's awesome wine list. They had wines you just don't see on a normal menu -- like our favorite Miner zinfandel from Napa Valley. And it was just a few blocks away from our place. We're very lucky to live in Bucktown where you can just walk down Damen or Division and have a crazy good meal right in your own hood!