The Berkshire Room
This hideaway just passed its fifth birthday—and many of the vintage spirit offerings here are far older. There’s a bottle of Old Grand-Dad from 1942, for instance, that provides the thrill of contemplating booze made in wartime. General manager Christian Hetter says the appeal of the old stuff is “more experiential than anything else—you’re almost interacting with a time capsule.” Crack it open. 15 E. Ohio St.
Longman & Eagle
The food is excellent at this still-vibrant whiskey bar-restaurant-inn, but the vintage-spirit collection is jaw-dropping. You might wander in and select a small pour of a 1971 Jim Beam, which spent 100 months in a barrel before bottling, and watch in awe as the bartender pulls down a commemorative decanter from a Veterans of Foreign Wars celebration in Indiana and gently breaks the original tax seal. The vanilla- and caramel-laden hooch inside is equally amazing. 2657 N. Kedzie Ave.
This jewel box bar inside the sprawling Chicago Athletic Association seats eight—but those lucky friends will experience perhaps the most dedicated vintage experience in the city. Beverage Director Paul McGee is something of a celebrity in this world, and his sleuthing achieves expression here, with a menu that often runs as far back as Old Hermitage from the 1920s and Old Overholt rye from 1909. 12 S. Michigan Ave.