Chicago's nightlife is as diverse as the city itself, offering a plethora of unique bars that go beyond the typical watering hole experience. For those seeking an unconventional night out, here are five distinctive establishments that promise more than just a drink.

The Owl

Nestled in Logan Square, The Owl stands out not just for its late-night hours but for its intriguing decor. One of its most talked-about features is a cassette tape vending machine—perfect for those nostalgic for the days of mixtapes. Additionally, a waterfall behind the bar adds a serene touch, harking back to the venue's past life as a Mexican restaurant.​

Source: Gallivant

The Heavy Feather

Also located in Logan Square, The Heavy Feather transports patrons to a '70s-era fern bar. Its standout feature is a taxidermied bear perched amidst lush greenery above the fireplace, blending seamlessly with the vintage-inspired decor and creating a cozy, retro ambiance.​

Source: The Heavy Feather

Empty Bottle

A cornerstone of Ukrainian Village, the Empty Bottle is renowned as a top rock club. Beyond its musical offerings, the bar houses eclectic artifacts, including baby doll heads and a police car door. These curiosities provide ample conversation starters as you enjoy performances from up-and-coming musicians.​

Source: Empty Bottle

The Burlington

In Logan Square, The Burlington embraces its dive bar aesthetic with minimalistic decor. However, one peculiar item catches the eye—a skunk tail hanging above the cash register. This quirky addition adds a touch of whimsy to the otherwise straightforward setting.​

Source: Flickr

Ed and Jean’s Tavern

Located in Bucktown, Ed and Jean’s Tavern exudes a vibe reminiscent of a grandparent's basement, filled with various knickknacks. The highlight is a train set running above the bar, enchanting patrons as it circles overhead and adding a nostalgic charm to the atmosphere.

Source: Block Club Chicago

Why settle for a standard bar when you can enjoy a cocktail alongside a police car door or a vintage cassette tape vending machine? Chicago’s quirkiest bars invite you to embrace the unexpected, one strange sip at a time.