Originally Posted by
JBord
Given the late start, I might skip the Hancock this trip and instead opt for a rooftop bar. If it's a nice night, most should be open. There are a lot, you can Google them. I'm not as hip as I used to be, so maybe someone else can suggest some good ones with a skyline view

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Personally I think going to some good neighborhood bars and enjoying a view of the city from a rooftop, while sipping a beer, as soon as its warm enough to go outside is probably the best way to experience Chicago as a Chicagoan would.
The challenge is that if it's a nice night and he's arriving at 10 or 10:30, most rooftop bars may be packed. That said, if I had my choice, I'd go to either Cindy's at the Chicago Athletic Association (directly across from Millennium Park with a great view) or JParker in the Hotel Lincoln (across from Lincoln Park).