On a recent Thursday night, while hail pelted Chicago, I was at [node:14701031 link=The Aviary;], doing what I suspect many locals will do here again and again: entertaining out-of-town guests. I was working my way through three aged martinis when a very serious woman came over and made a very serious inquiry: Were we interested in having a drink in the speakeasy below the Aviary—the Office? We were. And so 20 minutes later, after we’d finished our drinks and paid our bill, we followed her downstairs, where she led us into the cozy, handsome room to a private nook with a couch and two leather chairs.
Our server here seemed more at ease than those at the Aviary, and the cocktails ($20 each) were as complex, balanced and beautiful as those upstairs, though these arrived sans explanations and coy presentations. Although my group of four had already eaten dinner, it seemed like a waste not to order food, so soon we were working on creamed morels with toast ($25); plump shrimp in cocktail sauce ($30); and an ice-cream sundae for two ($25) that is the guiltiest of all guilty pleasures, a surreal convergence of Grant Achatz–level finesse and a Ben and Jerry’s Vermonster. 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.