...Best Fancy Italian: Roseangeli's on Wrightwood. The Italian really is the best I've had in Chicago. However having so much homecooked Italian I normally wouldn't choose to go to an Italian restaurant. However, has a very romantic decor to bring a high-priced date. (
link)
When you enter, you feel like you are in a house more than a restaurant. The intimate rooms can get a little loud, but that is what makes it fun. You feel like you are dining with friends. The food is consistently good, the portions are generous and the service is friendly. Do yourself a favor and leave some room for desert (the rice pudding and strawberries & chocolate are amazing!)