Speakeasy highlight: The Office in Chicago

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Trupti Devdas Nayak

Traveler . Writer . Photographer . Artist . I write about outdoor adventures at http://wanderlustandlipstick.com/blogs/trailbound and my travels at http://www.exploringthebluemarble.com
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The Office speakeasy in Chicago

Taking a rideshare into a nondescript part of Chicago lined with warehouses, one wouldn’t guess that this is also home to some of Chicago’s most famous restaurants and bars. Alinea was opened in 2005 by chef and owner Grant Achatz, who also founded Next and the Aviary, both in Chicago. His new speakeasy, “The Office” is just one jigsaw piece of the puzzle. Housed in the basement of the Aviary, getting to the Office feels as illicit as it must’ve been in the Prohibition Era, as we’re led through dimmed hallways, down a staircase, and given a key to open the door to … the 1900’s!

Interiors of the Office speakeasy in Chicago

Stepping into the Office, your senses are soothed by low lighting and the sight of chocolate-brown leather couches. Set in an intimate space that can seat only 14, the Office envelopes visitors with a warm hug. As we stepped up to the bar, our hostess Christiana greeted us. “First time here?”, she asked. “Yes!” we echoed. “Welcome to the Office!” she grinned.

Christiana pouring us a cocktail at The Office speakeasy in Chicago

Christiana was as spirited as the spirits she was transforming into delicious cocktails. We spent the next 3 hours (!!) talking to her, feeling like we had traveled back in time to the Prohibition Era, where speakeasies were a real thing, and indulging in any kind of alcohol sometimes meant a matter of life and death, even when dangerous moonshine was not involved. 

Some really old scotch at the Office speakeasy in Chicago

Christiana handed us a tome – the drinks menu – featuring dozens of pages filled with cocktails and spirits I couldn’t even have imagined. The Office boasts some of the most rare spirits still available, including a bottle of Scotch from the actual Prohibition era, an ounce of which will set you back by only $1100 USD.  Observing our unquenchable thirst (for knowledge …), Christiana offered another equally dense tome for us to browse through. This was an actual encyclopedia on the history behind each spirit, with additional context about it’s name, age, tasting notes etc. 

Steps leading to the basement of the Aviary restaurant

The Office won us over with it’s authenticity. Everything felt intimate and unpretentious. We had been granted a superpower to time travel and peek into the past without requiring to be snobbish. The cocktails and spirits were by far the best we’ve had. I tried the chartreuse for the first time (it’s a mix of yellow and green liqueurs, flavored with 130 different herbs, spices and flowers – an intense, herbal 80-110 proof medicinal spirit invented by monks).

Drinks at The Office speakeasy in Chicago

Unable to decide on a cocktail from the hefty menu, I asked Christiana to fashion one for me. She asked me 3 questions to get a sense for what I might like:

  1. My favorite spirit
  2. How do I take my coffee
  3. My favorite fruit

Christiana working it at the Office speakeasy in Chicago

Armed with these insights, she performed her deft magic for several minutes – measuring and pouring and tasting – finally presenting me with a crystal glass filled with dark caramel colored liquid. All her hard work paid off, it tasted absolutely delicious. After hanging out at the bar for a while, we wanted a break from balancing on the tall barstools, so we headed over to the leather couches nearby. It’s a lot more cozy and comfy to sink into the plush couch seating, but you don’t get the chance for eye-opening conversations with the bartenders as they whisk up cocktails and use pipettes to pipe up concentrated essences, perfecting the flavor profile for a drink. I’d definitely recommend sitting at the bar, especially if it’s your first time at The Office.

Concentrated essences to impart varied flavor profiles to drinks

When I asked Christiana how to get to the restroom, she smiled and handed me another key! The restrooms are outside the Office, so do not forget that if you step out, you need a key to get back in! Totally in line with the speakeasy vibe.

Key to the restroom outside

The best part at The Office was saved for the last. When it was time for our check, Christiana handed us a piece of folded parchment, sealed with an actual red wax seal that read “The Office”.

The check at The Office, a sealed parchment! How quaint!

We were amazed at their attention to detail. Opening the parchment, I discovered a neat, handwritten, itemized bill! What a great keepsake to always remind us of the memorable experience we had at the Office.

Our bill for the evening of indulgence at The Office speakeasy in Chicago

Have you been to The Office? What about other speakeasies in Chicago? Which one is your favorite? Let me know in the comments!

Happy Travels,

~ Trupti

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