Chicago’s got plenty of rooftop bars that afford bird's-eye views of glass and metal buildings. But take the hike up to the 13th-floor terrace at Cindy's (12 S. Michigan Ave., Loop) and you’ll get an ethereal sweep of the natural and urban: the blue from Lake Michigan, verdant treetops in Millennium Park, and shiny skyscrapers enveloping both edges of the view.

Now, you can enjoy your beverages al fresco without the hassle of going inside to order; they've opened a new outdoor bar, featuring wine, large-format cocktails, and boozy popsicles. Just be prepared to elbow your way toward a prime Instagram location.