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Discovering the Hidden Gems: Best Speakeasies in Chicago

Discovering the Hidden Gems: Best Speakeasies in Chicago

Chicago, often known for its rich history, stunning architecture, and vibrant cultural scene, has a lesser-known secret lurking beneath its streets – a world of speakeasies that pay homage to the Prohibition era. These hidden gems offer a unique and immersive experience, taking you back to a time when cocktails were crafted in secrecy. In this article, we'll unveil some of the best speakeasies in Chicago, share their intriguing histories, and even provide you with a classic Negroni recipe to enjoy at home.

A Glimpse into Chicago's Speakeasy Culture

During the Prohibition era in the United States, from 1920 to 1933, the sale, production, and transportation of alcoholic beverages were banned. However, this didn't stop people from enjoying their favorite cocktails. Instead, it gave rise to a clandestine and innovative cocktail culture centered around hidden bars known as speakeasies.

Speakeasies were tucked away in basements, behind unmarked doors, or within seemingly ordinary businesses. To gain entry, patrons often needed a secret password or a knowing nod from someone on the inside. These covert establishments were places where people could escape the restrictions of Prohibition and indulge in forbidden libations.

Today, many of Chicago's speakeasies pay tribute to this fascinating period in American history. They combine the allure of secrecy with creative mixology, making them some of the most sought-after drinking spots in the city.

The Violet Hour

Address: 1520 N Damen Ave, Chicago, IL 60622

Website: The Violet Hour

The Violet Hour is a standout among Chicago's speakeasy-style bars. Located in the Wicker Park neighborhood, it has garnered a reputation for its exceptional cocktails and elegant ambiance. This dimly lit cocktail lounge is known for its commitment to craft cocktails, which are carefully prepared by skilled mixologists.

The entrance to The Violet Hour is unmarked, making it a true hidden gem. Inside, you'll find an intimate and cozy space adorned with vintage-inspired decor. The bar's ever-evolving menu features seasonal and innovative drinks that push the boundaries of mixology. If you're a Negroni enthusiast, you're in for a treat, as they often offer their unique twist on this classic cocktail.

The Drifter

Address: 676-8 N Orleans St, Chicago, IL 60654

Website: The Drifter

For a speakeasy experience that truly captures the essence of the Prohibition era, visit The Drifter. This hidden gem can be found beneath the iconic Green Door Tavern in River North. The Drifter embraces the mystique of the 1920s, with its vintage decor, red velvet curtains, and intimate seating.

What sets The Drifter apart is its live entertainment. Guests are treated to an immersive experience with regular performances, including burlesque shows, jazz bands, and cabaret acts. Sip on a meticulously crafted Negroni or another classic cocktail while enjoying the unique and entertaining atmosphere.

The Library at Gilt Bar

Address: 230 W Kinzie St, Chicago, IL 60654

Website: The Library at Gilt Bar

The Library at Gilt Bar is a hidden treasure located beneath Gilt Bar in the River North neighborhood. This upscale speakeasy offers an atmosphere of sophistication and refinement. As its name suggests, The Library is adorned with bookshelves filled with vintage volumes, creating a cozy and intellectual ambiance.

Their cocktail menu features both classic and innovative drinks, expertly crafted by the talented bar staff. While exploring their cocktail offerings, don't miss the opportunity to savor a well-balanced Negroni.

The Owl

Address: 2521 N Milwaukee Ave, Chicago, IL 60647

Website: The Owl

If you're looking for a more casual speakeasy experience, The Owl in Logan Square is the perfect choice. This unassuming neighborhood bar offers a relaxed atmosphere with a fantastic selection of craft beers and cocktails.

While The Owl may not have the overt secrecy of other speakeasies, its cozy and welcoming ambiance makes it a hidden gem in its own right. It's an excellent spot to enjoy a classic Negroni while listening to live music or spinning some vinyl on their turntables.

The Darling

Address: 905 W Randolph St, Chicago, IL 60607

Website: The Darling

Located in the West Loop, The Darling is a contemporary speakeasy with a charming vintage twist. Its unique and whimsical decor, reminiscent of a Victorian-era parlor, sets it apart from other speakeasies in the city.

The Darling offers an extensive cocktail menu featuring both classic and signature creations. Their bartenders are known for their precision and creativity, ensuring that every cocktail, including your Negroni, is a masterpiece.

Crafting a Classic Negroni at Home

Now that you've explored some of Chicago's best speakeasies let's bring a piece of that hidden world to your home bar with a classic Negroni recipe. Here's how to make this iconic cocktail:


  • 1 oz Gin
  • 1 oz Campari
  • 1 oz Sweet Vermouth
  • Orange Twist or Slice (for garnish)
  • Ice Cubes


  1. Chill Your Glass: Begin by chilling your glass. You can do this by placing it in the freezer or filling it with ice and letting it sit while you prepare the cocktail.

  2. Measure and Pour: In a mixing glass, measure out 1 oz of gin, 1 oz of Campari, and 1 oz of sweet vermouth.

  3. Add Ice: Fill the mixing glass with ice cubes. The quality of ice can affect the cocktail, so use clean, filtered water to make your ice cubes.

  4. Stir: Stir the mixture well using a bar spoon or cocktail stirrer. Stirring helps to chill and dilute the drink slightly, creating a balanced flavor.

  5. Strain: Strain the cocktail into your chilled glass. Use a julep strainer or the mixing glass's built-in strainer to prevent ice from entering the glass.

  6. Garnish: To garnish your Negroni, express the oils from an orange twist over the drink. You can also add a thin slice of orange as an alternative garnish.

  7. Serve and Enjoy: Your classic Negroni is ready to be enjoyed. Sip slowly and savor the harmonious combination of flavors.

The Charms of Chicago's Speakeasies

Chicago's speakeasies offer more than just cocktails; they transport you to another era, providing a glimpse into a fascinating period of American history. Each of these hidden gems has its own unique character and charm, making them destinations for both cocktail enthusiasts and history buffs.

As you explore the city's speakeasies, remember to enjoy the craftsmanship of the cocktails, soak in the ambiance, and appreciate the nod to the past. And when you're back home, you can recreate the magic with a classic Negroni in hand, reminiscing about your secret adventures in the Windy City's hidden bars. Cheers!

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