I have a friend visiting from out of town who will, I am sure, want to have that whole "Hip Chicago" thing. He'll be visiting this weekend, and we will be going out on Saturday. I know that Saturday is a truly UN-hip night to go out, but that's what we've got.
This friend loves to bar hop, to go from place-to-place to see if the next place is better, has more interesting people, nicer drinks, etc. So we'll be settling in somewhere and already he has his mind on where we should go next. It's tiring :)
On the one hand I am thinking about trying one of the new dessert bars (Sugar, or Domaine which opened last night) and going somewhere nearby for dinner (Naha?). Or Nine/Ghost, or Aubriot and the upstairs, or Blackbird and its upstairs, etc.
On the other hand, we could do something much more real Chicago and less "Beautiful People" - which is probably the far "hipper" option :)
So for the second hand, where would you go? Leo's Lunch Room for dinner? West Town Tavern? Afterwards? Buddy Guy's? Webster's Wine bar? To keep in mind, we are in our mid-thirties and I'd prefer not to be either the youngest or oldest in the room :)