One of my favorite favorite restaurants in Chicago is Longman & Eagle in Logan Square. It's a gastropub and I know what you are thinking Chicago is full of gastropub so what's so special about this one. The difference is that they actually fulfill on both fronts - great drinks and great food. Maybe it was also that we came during a warm autumn night and got to sit outside and ate and drank to our heart's content, but I think the company that you're with can definitely make the food association that much greater and of course I was with Susan and Aleen.
They had a bunch of interesting small plate options so we couldn't narrow it down so we got three to share. This was the Ricotta Gnuddi with Asian Pear Black Walnut Jam, Butternut Squash Veloute and Brown Butter Sage Emulsion. Basically imagine a ricotta gnocchi that is fried and you get the picture. Yum is right.