Whiskey Business

Whiskey Business is a lively rooftop bar located in the heart of Chicago's Wicker Park neighborhood at 1367 N Milwaukee Ave, blending 1980s and 1990s nostalgia with an impressive whiskey-focused drinks program. Spanning approximately 3,000 square feet, the rooftop deck features over 100 varietals of whiskey alongside crafted seasonal cocktails and an expansive beer list, all enjoyed beneath the open sky. The fun, relaxed atmosphere includes 100-inch TVs for classic movie screenings and sports viewing, while the event calendar brings karaoke nights, stand-up comedy, and rooftop yoga to the mix. Weekend Brunch Club runs Saturday and Sunday mornings, and Taco Tuesday brings additional food options throughout the week. With shareables, comfort bites, and the spirit of a neighborhood hangout, Whiskey Business is a distinctively entertaining rooftop experience in one of Chicago's most vibrant districts.