Best Whisky Bars in Chicago

Delilah’s: Rocks and roll
Offers: Live music, Billiards
Dark, loud, and rowdy: the way whisky should be. This bourbon-centric bar offers over 700 whiskies. Punk Rock Mondays feature $1 beers, $2 Jim Beam shots, and free billiards. If that’s not your style, check the calendar for metal, ska, soul, alt-country, and even late-night movie screenings. Delilah’s steady stream of coveted custom bottlings includes collaborations with Compass Box Whisky Company and Chicago’s F.E.W. Spirits.

Longman & Eagle: Bourbon and a bed
Offers: Food, Flights, Whisky education
Eat, drink, and sleep without changing venues. Longman & Eagle has six uniquely designed rooms upstairs where guests can stay, starting at $95 per night. You may need a good night’s rest after working through two primary bars, the Michelin-star restaurant serving farm-to-table entrees, and the “off-site bar” (OSB), a micro-bar outside. Among the 400 whiskies, you’ll find dozens of daily specials priced at just $3 a pour.

Untitled Supper Club: A not-so-secret speakeasy
Offers: Live music, Food, Flights, Lockers
Step through Untitled’s secret entrance and descend the stairs back to the Prohibition era. Outfitted with lush red velvet booths, a large gilded mirror, a wall of lockers (VIP members only), and suspendered servers, the swanky Whiskey Library claims to stock the largest selection of American whiskeys anywhere—more than 500. Thursday nights offer bawdy burlesque shows while Wednesday, Friday, and Saturday deliver live music ranging from jazz and swing to folk and R&B.

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