Best Speakeasies In Chicago

The search for a speakeasy in Chicago can be a fun, if an anxiety-inducing adventure. After all, no one wants to look ridiculous fumbling around in public for an entrance. Luckily, this guide to the city's five best speakeasies ensures you won't make a fool of yourself as you pony up to the most exclusive bars. 

Get to The Green Door Tavern and walk downstairs toward the bathrooms. Knock on the door disguised as a floating shelf of knickknacks to be let into the circus-themed saloon that operated as an actual speakeasy during Prohibition. Its 45 cocktails are printed on individual tarot cards, with no more than 11 selected at random to be featured each night; there's the Basic Brah (whiskey, allspice, sherry and chamomile), the Forbidden Graphic Tee (rum, banana, limoncello, orgeat and Dumante) and a Malört-based cocktail aptly placed on The Devil card. Throughout the evening, various acts, running the gamut from burlesque dancers and jugglers to contortionist and singers, perform for guests.

Even if you do know where you're going, it's still easy to miss The Violet Hour's entrance, thanks to the building's constantly changing facade, which can range from a neutral paint job to colorful murals by local artists. So instead keep your eye out for the overhead lamp—if it's lit, you'll find the unlocked entrance to this modern speakeasy right below. There's no cell phone use or shoddy attire allowed once you pass through the towering curtains and into the dimly lit, slate-blue room with high-backed velvet chairs and elegant, minimal decor.

While making your way to the downstairs bathroom at Gilt Bar restaurant, you might turn your head in time to see a glimmer of light from what looks like a service closet. The door leads to a long and winding hallway, where you'll find a secret room offering diners—if they know to ask their host for it—the opportunity to eat and drink in a private, candlelit space full of velvet, leather and books.

You'll have to do a bit of work if you want entrance into this Prohibition-inspired bar, located underneath the Old Chicago Inn. Unless you're an overnight guest (in which case, you'll be given the ever-changing password), you'll have to either be a member to enter or know someone who is. The drink menu pays tribute to classic 1920s-era tipples, like the Manhattan, mai tai and Singapore sling. 

It's unlikely you'll discover this 12-seat bar, sandwiched between Fat Rice and its Bakery, unless you really know your way around. Walk through The Bakery (doing your best to ignore pastry chef Elaine Townsend's miso fudge brownies) and look for the yellow script that points to a room marked Ladies. Bathed in moody red light and decorated with Asian pinups, the place serves inventive cocktails in tiki tumblers and, in some cases, a side of fire, like the Burning Bird, a tropical elixir for four presented with a flaming orange peel that's ignited tableside.  

Ximena N. Larkin is a writer and communication strategist based in Chicago. Find her at @XimenaLarkin on Instagram and Twitter.