The Boss Bar

Mezcal cocktails + Chicago's best tacos

Gus' Sip & Dip reinvents the neighborhood tavern, blending nostalgia with a modern edge. Named No. 27 on North America's 50 Best Bars, awarded 1 PIN by The Pinnacle Guide, and winner of the 2026 Jean Banchet Award for Best New Bar, Gus' operates on a first-come, first-served basis. The cocktail program, curated by renowned Beverage Director and Partner Kevin Beary, features 30 reimagined classics organized by spirit, all just $12 with spirit-free versions available. Monday through Friday, Happy Hour offers a rotating cocktail of the day for $6. The food menu, crafted by Chef Partner Bob Broskey, rounds out the experience with elevated tavern fare.

Holloway's Bar is an homage to Chicago's rich history as the candy capital of the world. Since the late 1800s, the River North area in particular - has been a dynamic hub for the Windy City's sweetest industry. A key member of this confectionary revolution was Milton J. Holloway, who was the original producer of a chocolate-covered caramel treat called a "Milk Dud". Holloway's serves light fare, sharing plates, cocktails and a great late-night happy hour. The menu includes salads, sides, and kids' options.

A lively and vibrant mezcal and tequila bar that embodies the heart and soul of Mexican Hospitality.

Introducing Encanto, the newest addition to Chicago’s growing agave scene right in the heart of River North. Mezcal has everything one would need in a good spirit—history, culture, and layer upon layers of flavor. Every mezcal has its own history, every bottle is a whole new world; making it an easy-going and fun ingredient to work with because of its range. Encanto’s dedication to sustainability and supporting those who put care and attention into the production of tequila and agave is clear through the diverse representation of brands and producers that each bring a distinctive and eclectic option to the table. Encanto's hours vary- please call us in advance to plan your next visit!

A bar at 333 N Dearborn St in Chicago.

This upscale sports bar offers an eclectic menu in a slick, loungey space with plentiful plasma TVs.

For us, the bar is the center of where we play and eat. Our team will put a drink in your hand and ideas in your head for a good time in Chicago.