Outdoor Terrace Sky Bars

Perched atop the Chicago Athletic Association Hotel, Cindy's offers breathtaking views of Millennium Park, The Art Institute, and Lake Michigan. The airy, glass-enclosed space features communal tables and an open-air terrace with fire pits. Their seasonally-driven menu focuses on fresh, locally-sourced ingredients paired with craft cocktails, making it one of Chicago's most sought-after rooftop destinations.

Perched on the top floor of The Envoy Hotel in Boston's vibrant Seaport District, Lookout Rooftop offers breathtaking views of the Boston Harbor and city skyline. The stylish space features comfortable lounge seating, fire pits for cooler evenings, and a sleek bar serving creative craft cocktails. During summer, guests can enjoy flights of rosé and refreshing pitcher cocktails, while winter brings heated igloos that transform the space into a cozy seasonal retreat. A hotspot for both locals and visitors, Lookout Rooftop frequently tops lists of Boston's best rooftop destinations.

Located nine stories above Philadelphia's iconic Benjamin Franklin Parkway, Assembly Rooftop Lounge at The Logan Hotel offers one of the city's most impressive vantage points. With sweeping views of the Benjamin Franklin Parkway, Philadelphia Museum of Art in one direction and City Hall in the other, this sophisticated outdoor space features intimate seating pods equipped with fire pits, plush pillows, and comfortable couches. The well-crafted cocktail menu includes seasonal specialties alongside classics, while the small plates menu offers upscale bites perfect for sharing. Reservations are recommended for this in-demand urban oasis.

Located high above 2nd Avenue in downtown Seattle, The Fog Room at The Charter Hotel combines stunning views with sophisticated ambiance. This elegant sky lounge and terrace offers panoramic vistas of Puget Sound and the Seattle skyline, creating the perfect backdrop for handcrafted cocktails and small plates featuring seasonal Pacific Northwest ingredients. The sleek, modern space transitions seamlessly from indoor luxury to an outdoor terrace where guests can enjoy Seattle's famous sunsets. With its sultry atmosphere and expert mixology program, The Fog Room delivers a refined rooftop experience that captures Seattle's dynamic spirit.