Upstairs at The Gwen

In Chicago, finding a destination that feels right year-round can be a challenge. Upstairs at The Gwen, however, makes a compelling case for its place among them, seamlessly transitioning with the city’s shifting seasons. This rooftop terrace, set within the historic McGraw-Hill building, offers an adaptable occasion for any calendar. In warmer months, it’s a bright, open-air retreat for sunny cocktails. Colder weather transforms the space into a cozy haven, complete with tabletop fire pits and even a curling rink.\nThe setting is distinctly urban, with views framed by the grand architecture of the surrounding buildings rather than distant panoramas. Located five floors up, the atmosphere is one of sophisticated seclusion just a block from the energy of Michigan Avenue. The Art Deco-inspired design provides a stylish backdrop for a crowd that comes for everything from a weekday happy hour and live jazz to a weekend Tipsy Tea, a boozy, high-energy take on the traditional afternoon service.\nWhile the location provides a clear draw, the beverage program is crafted with intention. The cocktail list is known for being inventive and seasonal, with creations often named after Chicago landmarks. The kitchen has become known for shareable small plates and satisfying options like truffle fries and various flatbreads, designed to complement the drinks and the social atmosphere. The versatility of the offerings makes this a reliable choice for a range of occasions, proving that a rooftop destination can be for all seasons.