Hidden Speakeasies in Chicago & The Best Apartments Near Them

August 5, 2025

Looking for Chicago’s best hidden speakeasies? Whether you’re a cocktail lover, nightlife enthusiast, or simply want to uncover the city’s secret spots, these hidden bars offer unforgettable experiences - many just steps away from Reside Living apartments. If you're searching for apartments near Chicago’s top speakeasies, this list is your perfect starting point.


Magician holding a top hat and wand in front of a red curtain, performing a trick.

Chicago Magic Lounge – A Hidden Gem in Andersonville

Location: 5050 N Clark St, Chicago, IL 60640

What Makes It Special: Tucked behind a faux laundromat, this vintage-style venue blends magic, live performances, and craft cocktails in a one-of-a-kind setting.

Why You’ll Love It: This speakeasy offers an immersive 1930s vibe, perfect for date nights or entertaining out-of-town guests.

Nearby Reside Apartment: 5425 N Clark is just a short ride from the magic of Andersonville and its hidden hotspots.


A woman in flapper attire smiles, holding cash. She wears a headband, gloves, and a feather boa against a red background.

The Gatsby – Speakeasy in Lincoln Park

Location: 3125 N Broadway, Chicago, IL 60657

What Makes It Special: Located in the Bourgeois Pig behind an unmarked door beneath the bustling Wrigleyville scene, The Gatsby offers a secret 1920s cocktail bar experience with velvet booths and jazz-era ambiance.

Why You’ll Love It: Think Great Gatsby meets modern mixology - perfect for an upscale night out without leaving the neighborhood.

Nearby Reside Apartments: Lincoln Park – Located in Lincoln Park, you're within walking distance of The Gatsby and other hidden gems. Plus, you'll have easy access to restaurants, shops, and the lakefront.


Smiling woman in a flapper outfit holding money, wearing pearls, gloves, and a feathered headband. Red background.

Mile High Cocktail Club – A Sky-High Secret in West Loop

Location: 205 N Peoria St, Chicago, IL 60607

What Makes It Special: Located in the heart of West Loop, this elevated speakeasy channels the glamour of a 1960s first-class airport lounge - complete with vintage décor, plush seating, and jet-setting cocktails.

Why You’ll Love It: Retro charm, sleek design, and limited access make it one of the best-kept secrets in West Loop.

Nearby Reside Apartment: Gild – Around the corner from Gold Coast, this apartment community blends comfort and convenience with easy access to nightlife, dining, and CTA lines.


Woman in green sequined dress with feathered collar, arms raised in dance pose. Dark background.

Bordel – Vintage Paris Vibes with Burlesque in Wicker Park

Location: 1721 W Division St, Chicago, IL 60622

What Makes It Special: Located above Mama Delia, Bordel is a Parisian-style speakeasy with candlelit tables, burlesque shows, and live jazz.

Why You’ll Love It: Romantic, mysterious, and packed with atmosphere - it’s one of Chicago’s most iconic secret bars.

Nearby Reside Apartment: 1846 W Division – Live steps away from nightlife, music, and culture while enjoying a quiet retreat with upscale features and modern design.

A person holds a coupe glass with a cocktail garnished with a blackberry and a miniature vial of liquid hanging from the rim.

Find Your Chicago Apartment Near the Best Hidden Bars

If you love discovering secret spots, Reside Living puts you in the center of it all. Our apartment communities are located near some of the best hidden speakeasies in Chicago - making it easy to enjoy everything the city has to offer, right outside your door.

Looking for an apartment near Chicago nightlife?


Explore ourReside Living communities today and find a place that fits your lifestyle—whether you’re drawn to Andersonville magic, West Loop exclusivity, or the electric energy of Wicker Park.

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