Estate Ultra BarGoose Island | Website
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This massive River West bar has a rooftop deck with several decked-out rooms that give the impression you're a weekend guest at a modern summer estate. The sleek interior features smooth wooden tones, along with muted colors and multiple fireplaces. To drink, expect a dozen or so custom cocktails, along with 28 beers on tap (many of them local) and a well-rounded wine list. To eat, there's shared plates like lobster mac, steak frites and deviled eggs, plus a line-up of American cuisine such as the Estate burger with a patty made from short rib, brisket and chuck, topped with dunbarton cheddar, tomatoes and pickles on a sesame brioche bun.