I found your page because I'm thinking of going to Chicago maybe this October. What's your favorite bar or neighborhood to go out for drinks?
In my opinion, River North is the spot to be.... nightlife, restaurants, hotels, not far from the magnificent mile. Two great hotels, that actually have popular rooftop lounges are The Godfrey and theWit-Double Tree. I’m that area there are also a ton of bars and clubs. Some popular spots are: Bottled Blonde, El Hefe, Trophy Room. Concrete Cowboy, Public House, Joy District, Cuvée, Underground, Electric Hotel, and Tunnel... if you are interested in any of these places, I could help you with guest lists, tables, bottle service, etc. if needed. Also, around that time, there will probably be a few bar-crawls for okerober fest, so that could be an option for you too, just keep in mind, most bar crawls are ticketed events