Perched atop The Robey, one half of Wicker Park’s new boutique hotel diptyque, The Up & Up is mesmerizing and minimalist and seats just a few dozen. It may conjure drinking déjà vu if you’ve ever had the pleasure of sipping a cocktail at the rooftop bar of Mexico City’s Hotel Condesa DF: Both properties are run by Grupo Habita, notable for small and stylish urban lodging with tastefully tiny bars. It’s located on the roof of a historic Art Deco flatiron building overlooking the Damen/North/Milwaukee intersection, which offers jaw-dropping views of the downtown skyline from chairs spread over the unique triangular footprint. THE DRINK TO DRINK: Try one of the seasonal cocktails, although with views like these, a menu of tap water would suffice. KNOW BEFORE YOU GO: If you’re afraid of heights, skip the views and stake out the tiny boîte tucked in the foot of the building’s flagpole.