Located atop the historic Raffaello Hotel, Drumbar is one of the hottest spots on Chicago's Gold Coast with good reason. This stylish rooftop bar is run by The Underground's Benjamin Newby, so the drinks to match the cinematic views. Occupying the 18th floor of the hotel, it's an attractive space but the real draw is the spacious rooftop terrace. Despite its sky-scraping setting, they've gone for a speakeasy vibe which is reflected in a cocktail list that goes heavy on the whiskeys, bourbons and scotches. The Ruby mixes bourbon with apricot liqueur, lime juice and raspberries while the Smoke is a blend of rich, peaty scotch and lapsang tea. The atmosphere is glamorous in an understated, urban way and that view is simply glorious, especially in the early evening. It's popularity is such these days that it's better to go earlier in the week if you want to sample Craig Schoettler's progressive cocktails. He's the former executive bar chef at The Aviary and makes the kind of experimental, layered, reative drinks you would expect from someone with his background, having worked under Grant Achatz.