Mastro's Steakhouse - Chicago Chicago

Mastro’s Steakhouse sits on North Dearborn Street, a five-minute walk from the House of Blues. The venue holds a 2024 Wine Spectator Excellence Award and offers a menu of seafood and grills. The room runs smart and elegant, leaning into a formality that feels distinct from the quick-turnover spots nearby.

Most steakhouses in this district rely on tradition to attract tourists, but Mastro’s relies on its wine program to drive the experience. It captures a more focused, beverage-centered crowd than the nearby Magnificent Mile corridor, where volume often takes precedence over cellar depth. If you prefer a dinner guided by the selection of the bottle rather than the bustle of the street, this is the room to choose.