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Food & Wine

Modern Speakeasies in Chicago

Last Updated

September 15, 2023

Modern speakeasies have become a distinctive part of Chicago's nightlife scene, paying homage to the city's history while offering patrons an unforgettable experience. From upscale establishments like The Violet Hour to tiki-inspired havens like Three Dots and a Dash, Roaring Twenties-inspired Bordel, and the aviation-themed The Mile High Cocktail Club at Four Seasons Chicago, these hidden gems transport visitors to another time and place. Whether you're seeking an escape from the ordinary or simply looking to indulge in expertly crafted libations, the modern speakeasies of Chicago have something for everyone.

The Mile High Cocktail Club at Four Seasons Chicago

Adding to Chicago's vibrant speakeasy scene is The Mile High Cocktail Club, located within the prestigious Four Seasons Hotel in downtown Chicago. This aviation-themed speakeasy takes inspiration from the golden age of air travel, offering patrons a unique and nostalgic experience. As you enter through the inconspicuous door, you are greeted by a stylish interior reminiscent of a luxurious airplane cabin.

The cocktail menu at The Mile High Cocktail Club pays homage to classic aviation drinks, with a modern twist. From the Aviation cocktail to the Paper Plane, each drink is expertly crafted using high-quality ingredients and innovative techniques. The bartenders here are true artists, creating visually stunning cocktails that are as delightful to look at as they are to taste.

In addition to its exceptional libations, The Mile High Cocktail Club offers a range of small plates and appetizers to complement your drink of choice. The menu features gourmet bites inspired by international flavors, allowing guests to embark on a culinary journey while enjoying their aviation-themed cocktails.

The Violet Hour

Located in Chicago's Wicker Park neighborhood, The Violet Hour is an upscale speakeasy that exudes sophistication and mystery. As you approach the unmarked entrance, anticipation builds, and upon entering, you are transported to another era. The dimly lit interior, plush velvet seating, and classic jazz tunes playing softly in the background create an intimate and exclusive atmosphere.

The cocktail menu at The Violet Hour is carefully curated, featuring innovative concoctions crafted by expert mixologists. From the classic Old Fashioned to more adventurous creations like the Lavender Mule, each drink is a work of art. The attention to detail extends beyond the drinks themselves; the garnishes are meticulously prepared, adding visual appeal and enhancing the overall experience. The Violet Hour truly embodies the essence of a modern speakeasy, offering a refined environment where patrons can indulge in exceptional libations.

Three Dots and a Dash

Tucked away in the River North neighborhood, Three Dots and a Dash is a tropical-themed speakeasy that transports guests to a world of exotic flavors and tiki-inspired decor. Upon descending the stairs into the basement establishment, you are greeted by a vibrant space adorned with bamboo accents, colorful lighting, and an extensive collection of rum bottles.

Three Dots and a Dash boasts an impressive menu of handcrafted cocktails, each adorned with elaborate garnishes and served in unique vessels. The Zombie, a signature drink at this speakeasy, is a potent mix of different rums, tropical juices, and secret spices. Sipping on one of these expertly crafted libations, you can almost feel the warm ocean breeze and imagine yourself on a distant island paradise.


Moving further into the city, we stumble upon Bordel, a Roaring Twenties-inspired speakeasy located beneath the bustling Flatiron Arts Building in the Wicker Park neighborhood. As you step through the discreet entrance and descend into the underground space, you are transported to the roaring twenties, complete with live jazz performances and a vintage ambiance.

Bordel offers an alluring selection of classic cocktails, with each drink meticulously prepared using premium spirits and house-made syrups. Their Old-World glamour extends beyond the beverage menu; the establishment also hosts burlesque shows and other eclectic performances throughout the week. It's not just a bar; it's an immersive experience that allows you to immerse yourself in the decadence and excitement of the Jazz Age.

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