The best Italian restaurant in Chicago by far is Volare. It's kind of hidden, although still very close to Michigan Avenue, and is definitely a cozy atmosphere. Nights are very busy and you might have a hard time getting a seat, but it is well worth the wait. Prices are reasonable (about $12 for a plate of pasta) and the servings are huge. The best meal there? Caesar salad, gnocchi with vodka sauce, and tiramisu! Service is usually great, although my one complaint is that even when you make a reservation, getting seated still tends to take a while. I definitely recommend coming here, either for a date or for a group dinner!