> I will be at a conference at the O'hare intercontinental hotel. I have
> not booked accommodations there. I like Marriott or Hilton.
If that is the hotel I'm thinking of, it's actually well within walking distance to the Rosemont (River Road) El/subway station.
Big question here. Will you have a vehicle or will you be using public transit or taxi?
If you have a vehicle, you're much better off staying out in the 'burbs, since parking is usually not included with the downtown hotels and is very expensive.
It's about a 35-45 minute train ride from the O'Hare area to downtown and about an hour to the Boystown/Lakeview area. Most hotels in the O'Hare area have a free shuttle to/from the station.
If you don't have a vehicle, you can stay downtown and be closer to the action and take the train out to your conference in the morning.
> I was just thinking of a nice evening, maybe watch something or dancing, etc.
There are countless dance bars in the Lakeview/Boystown area. Most all of them should be welcoming.
You'll probably hear of Hunters Dance Club, which is not too far from O'Hare. It gets mixed reviews from the TG crowd. They "card hard" at the door and there are some reported hassles when the photo does not match the appearance. In all fairness, last time I was there I enjoyed it, but I really don't have any desire to go back until that lingering issue is settled.
If you haven't seen our Big List of recommended place, look here:
http://www.geekbabe.com/annie/pinkven/