The close-up view of the Wrigley Building from the 16th floor of Trump Tower is a sight best appreciated by a local. So if you’re looking to throw down $20 for a glass of wine or a cocktail, you’d be hard-pressed to find a posher playground.
Height: 16th floor Drink of choice: Snapdragon: Grey Goose, strawberry ginger ale and prosecco If you’re eating one thing: It better involve truffles—otherwise, what's the point? Wait for a table: Can stretch pretty long at peak times; call ahead Crowd: Businessmen, hotel guests and glammed-up couples
401 N Wabash Ave (312-588-8030). El: Red to Grand. Bus: 2, 3, 29. 2:30–11:30pm (weather permitting). Average glass of wine: $21. Open mid-May.