Upstairs at The Gwen

Upstairs at The Gwen is an Art Deco-inspired rooftop bar and restaurant on the fifth floor of the historic McGraw-Hill building at 521 North Rush Street in Chicago. The venue offers seemingly endless skyline vistas through its laid-back, twinkle-lit atmosphere featuring both an elegant indoor lounge and open-air terrace. Handcrafted cocktails and a curated wine program complement seasonal small plates and breakfast offerings, while live jazz performances by the Cosmic Jaywalkers grace Wednesday evenings. The rooftop transforms seasonally, featuring warm drinks and fire pits in winter, making it a year-round destination for sophisticated cocktail enjoyment with panoramic city views.