At the height of Prohibition, getting a whiskey on the rocks required sleuthing: finding the right alley door, knowing the secret password (and the bouncer). Liquor’s return to law-abiding folks in 1933 didn’t diminish the lure of a hideout serving great hooch. The thrill of the hunt—and the reward of a modern craft cocktail—make these speakeasy bars a trip.
The Office, Chicago You don’t just roll into this off-the-radar bar at The Aviary restaurant in the West Loop neighborhood. First, you make a dinner reservation. Once seated, try the In-the-Rocks cocktail (a snowball-size ice cube injected with liquors like absinthe, vermouth and rye). Casually ask your waiter if there’s room at The Office. After the waiter does some checking and gives you a few discreet head nods, follow the manager downstairs. With a turn of a key, you’re in. The booze menu is impressive—some of the bourbon has been aged for decades—but it’s more fun to trust the mixologist to make you a signature cocktail. theaviary.com
The Blind Lion Speakeasy, Rapid City, South Dakota “I have a ticket to see the blind lion.” Remember that phrase after owner Tony DeMaro texts you instructions for accessing the speakeasy below Murphy’s Pub and Grill. (How to get that text? Search Murphy Pub’s Facebook feed or ask pub staff.) Waitstaff get into the speakeasy spirit: Men in suits sport curled moustaches, and women wear glittering flapper-inspired dresses. A mainstay cocktail is the potent, herb-flavor absinthe-based Green Fairy. (605) 791-2244; murphyspubandgrill.com
International Exports Ltd. (Safe House), Milwaukee Inside the stately offices of International Exports Ltd., Ms. Moneypenny will ask you for a password. If you don’t know it, you’ll have to pass a test (impersonate a Ninja, maybe?) proving you are part of their spy network. A secret passage leads to rooms displaying spy memorabilia dating back to 1966. Take a seat in the bar, but beware of the trick stool that sinks at a slow pace and the booths that rotate. In keeping with spyesque tradition, the Ultimate Spytini arrives shaken, not stirred. (414) 271-2007; safe-house.com
Manifesto, Kansas City, Missouri The Rieger Hotel Grill is a great place for dinner, but on this mission, you’re headed for the alley. At the unmarked metal door, hit the buzzer and wait for it to open. Head down the scuffed stairs and through a narrow hallway until you find yourself in a cozy, candlelit 48-seat speakeasy. Here, an old-school rule discourages cell phone use. Sit at the high-back leather chairs at the bar to watch suspender-clad staff whip up libations like the Smokin’ Choke—heavy on the whiskey. (816) 536-1325; theriegerkc.com/manifesto