Drumbar The gorgeous 18th-floor bar of the Raffaello Hotel boasts a handsome, dim interior full of tufted leather banquettes and a chic exterior deck with open fireplace pits. The addition of Aviary vet Craig Schoettler has brought seriousness to the cocktail program; we recommend the full-bodied Pineapple, in which a sprig of mint is dipped in Chartreuse and set aflame. Up the staffing and training, and Drumbar will have everything it needs to transcend its hotel-bar status. 201 E Delaware Pl (312-924-2531). Mon–Wed 5pm–midnight; Thu, Fri 5pm–2am; Sat 5pm–3am (closed Sun). Average cocktail: $13.
The Grill on the Alley If the plethora of newspaper clippings in the lobby is any indication, this import from Beverly Hills was the restaurant in 2000. Now that the buzz (and, as a result, the crowds) has died down, the effect is just the opposite: You can sink into one of the roomy leather booths, put down a few well-executed classic cocktails, tear into a citrus-marinated skirt steak (or, if you’re feeling a little heart-healthy, the cedar-planked barbecue salmon) and relax, knowing that nobody will ever find you. The Westin, 909 N Michigan Ave (312-255-9009). Breakfast, lunch, dinner. Average main course: $30.
The Office If you thought getting a ticket to Next was hard, you’ve never heard of the Office, the intimate basement speakeasy beneath Grant Achatz’s Next/Aviary compound. The cocktails ($20 each) are as complex, balanced and beautiful as those upstairs, though these arrive sans explanations and coy presentations. In every part of the experience—the exclusivity, the perfection, the nostalgia—lies the genius of the Office, where to spend lavish amounts of money on fleeting pleasures feels not like a sacrifice but rather a distinct privilege. 955 W Fulton Mkt (text 312-972-7641). Reservations required. Average cocktail: $20.
RL A restaurant in a preppy clothing store on Michigan Avenue—could anything be more precious? The short answer is no. But while you will undoubtedly be entertained watching fur-clad women whisking in and sitting down for two bites of a Waldorf salad, there are a few other things worth experiencing here. The Dover sole, for instance, is prepared tableside with so much pomp you’ll think you’re eating with the Queen of England. Us? We’ll take an expertly shaken sidecar and a burger, which, surprisingly, is pretty damn good. 115 E Chicago Ave (312-475-1100). Brunch (Sun), lunch, dinner. Average main course: $29.