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Unfortunately, the internet ensures that nothing — even today’s modern speakeasies — is truly “secret” anymore. But these four exclusive Chicago bars can still be difficult to find and even more difficult to access even with the right info.
Room 13 at The Old Chicago Inn Bed & Breakfast (Lakeview)
Room 13 may be the city’s most exclusive speakeasy. The nondescript entrance is tucked neatly into an alleyway near the corner of Belmont and Sheffield. There are only three ways to gain entry: know the password, be a guest of the adjacent Old Chicago Inn B&B, or purchase a yearly membership. This is a true Roaring Twenties-era jazz club and guests are expected to dress accordingly (jackets for the gentlemen, cocktail attire for the ladies). They’ve even gone so far as to trademark the tagline “Drink in Some History™”. For $55 per couple, B&B guests can choose to add a Speakeasy Flight to their stay. The package includes a sampling of four classic cocktails, all handcrafted while the bartender describes their significance and historical influences.
The Office at The Aviary (West Loop)
One of Chi-town’s most classic speakeasies is The Office at The Aviary. There are only two ways to get into this basement venue: either by invitation or by booking a private party of at least 16 people. The small plate and cocktail menus are as pricey as the bar is exclusive (think $20 and up for a “typical” cocktail). Although the joy of telling your significant other that you’ll “be staying late at The Office tonight” is well worth the price of admission.
Related: Micro Guide: Chicago
The Violet Hour (Bucktown)
As perhaps the city’s oldest speakeasy, The Violet Hour is somewhat of an institution among Bucktown locals. The bar is open to the public, provided you can navigate your way through the tacky, eclectic mural outside. There’s no sign and only a small door handle marks the entrance. As an added bonus, visitors can register for TVH’s Master Beverage Classes. Each class introduces bartending newcomers to a distinct aspect of classic mixology, including Syrup 101 and Seasonality and Bitters: Function versus Fashion.
East Room (Logan Square)
Imagine a private DJ party in your friend’s basement, then add a bit of garish gentleman’s club decor. That’s about the size of East Room where simple, exposed brick, jet black curtains, and cheap canned beer set the scene. The entrance to this secret no-frills bar is hidden behind a nondescript black door in an alley off Medill. There’s no signage of any kind and only a simple red light above the door indicates when the bar is open. Unlike the city’s other modern speakeasies, the bar menu here is modestly priced and don’t expect to find anything too fancy.
(Photo via Flickr)