The Violet Hour
I've heard a lot about The Violet Hour (it seems like a place worth visiting!) -- I just have a couple of questions:
1) It says on their website that they don't accept reservations. Is it generally hard to get in? And if there is a wait, is it usually long?
2) If you were to choose between The Violet Hour and The Aviary, which would you suggest?
3) Is there somewhere else that I'm missing? (I've already been to Sable, another cocktail place that comes up on this board frequently)
1. As mentioned above, go early, go on an off night.
2. Depends. The Aviary is a one of a kind cocktail restaurant. Very few places like it in the USA. Maybe Booker & Dax in NYC or Rogue24 in DC. I'd say try it at least once, it's truly unique. I don't go there for a Manhattan, I go there for stuff like the Ginger, Oolong, In the Rocks, etc. There's no bar to sit at, though. But you can make a reservation. Also you can't go off the menu or get a bespoke drink, unless you go to the Office speakeasy in the basement. And the food is literally single bites. But they have an el Bulli menu right now until the end of May.
3. To add to danimalarky's suggestions of Scofflaw, Whistler, Barrelhouse Flats, and what you already have (Aviary, Sable, Violet Hour), what about Yusho, Maude's, Bar Deville, The Drawing Room? Been hearing good things about the program at Acadia, too.
re 1 -- honestly, it depends. If you go early on a weeknight, no wait. If you show up at 9pm on a Saturday night, there will be a long wait. The smaller your party, the easier it should be. The person at the door can also take your phone number and you can hang out somewhere nearby (just do not miss that phone call!). One option is across the street at Big Star. This is a very dangerous 1-2 combination, however, as I can personally attest.
re 2 -- personally i'd go with the Violet Hour but that's just because I like sitting at the bar and engaging with the bartender. Also, I've found the Aviary to skew a little too gimmicky for me (ie. the Manhattan served in a flask -- it just made it hard to drink more than anything else).
re 3 -- one of the newer places in the city is called Scofflaw. It gets a lot of love on the other foodie site in Chicago for both the drinks and the food (though I think it's a place where the drinks are the focus). It's not easily accessible via CTA, but it's not too out of the way, either. I also like The Whistler, in Logan Square. Very small and they have often live music (and depending on the act, that could be a positive or a negative -- I'd check their website first), this was Paul McGee's spot for a long time. He's gone now but I haven't found The Whistler to be worse off for it. Lastly, there's Barrel-house Flats in Lincoln Park. Yes, the home of sports bars now has a legitimate cocktail destination -- I'd just be sure to go earlier in the evening, if possible.