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Unlike an average, cookie-cutter bar, lounges have a unique vibe and trendy atmosphere that sets these establishments apart from the rest. Many times swanky and other times quirky, lounges in the Windy City offer libations, music and well, a lounge-like hangout spot for you and your friends. Here’s five to try:


Situated in an unconventional location – the 18th floor of a medical building – GreenRiver boasts one-of-a-kind cocktails inspired by Irish Americans as well as snacks and full plates. Settle in on the outdoor terrace at this trendy lounge in the Streeterville neighborhood, and you’ll understand why Chicago Magazine named GreenRiver one of the best new bars for 2016.

The Violet Hour
At The Violet Hour in the Wicker Park neighborhood, high-backed blue leather chairs, crystal chandeliers and dim lighting create a speakeasy vibe. Patrons can enjoy a rotating list of pre-Prohibition style cocktails at one of three unique areas, but ensure you take note of the strict house rules that ban items like cell phones, reservations and light beer.

The Drop Lounge
Named after their signature craft shots served “bomb style,” the Drop Lounge is an underground shot and cocktail bar on Lincoln Avenue. Step down into the cave-like lounge, and you can enjoy signature drop shots like the “Fire Dancer” with Fireball whiskey and Angry Orchard cider or the “Adios Aloha” made with jalapeno-infused tequila and pineapple cider before hitting the dance floor.

Zebra Lounge
Since 1929, the Zebra Lounge has been entertaining bar-goers in the Gold Coast neighborhood with martinis, cocktails and nightly live piano music. Tucked inside an apartment building, the Zebra Lounge’s eclectic décor of leather booths, maroon walls and zebra-striped lamps mimics the wide-range of patrons at this piano bar and lounge, which has the third-oldest liquor license in the city.

M Lounge
For an intimate and laid-back lounge experience, head to M Lounge off Wabash Avenue in the South Loop. Leather couches, candlelight and suede chairs create a warm and comfortable atmosphere where you can enjoy jazz music with friends while sipping on martinis like the “Orange Dreamsicle” made with mandarin vodka and Cointreau or the “Yummy Bear” with pear vodka and peach schnapps.