re: Trip to Chicago

Mate, have some cocktails at rebar in Trump tower lounge. It is one of the best views in the city and a really feng shui/pleasant space (so much better than the shitty Hancock tower which is cramped and hot and blah) and while the drinks are about $15 each, you get complimentary snack plate with wasabi peas, pretzels, greek olives, nuts, etc. that would easily run $10 if you had to order it. It's a classy way to spend an hour or so. Cocktail waitresses are tasty as frick. Dress to impress.

Picture below is at night but I actually like 5PM or so to watch all the people heading home from work, etc. I like that you're high enough to enjoy the view but low enough to people and boat watch.