Elevating sophistication, Z Bar sits on the 6th floor of The Peninsula Chicago, providing stunning vistas of Water Tower Place along Michigan Avenue. This rooftop destination features an internationally-inspired menu showcasing shareable options such as caviar potato bites, Mediterranean flatbread, and tuna tartare. The beverage selection includes timeless cocktails like aperol spritzes, old fashioneds, and mojitos, alongside four distinct gin and tonic preparations. The Nolet Dry pairs orange, rosemary, and Indian tonic, while the Malfy Originale Dry combines lemon, coriander, and Mediterranean tonic. 108 E. Superior.
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Crowning the tallest structure in Wicker Park, The Up Room resides atop the Robey hotel. This combined indoor-outdoor destination showcases sweeping panoramas of Chicago’s iconic skyline and neighboring areas. Seasonal cocktail selections feature inventive creations such as the Oaxacan on Broken Glass, blending mezcal, Ancho Reyes, Angostura, and Hellfire Bitters, and the Grotto Smash combining vodka, blackberry, mint, lime, and Angostura. Arrive promptly to claim a seat in the Grotto, an exclusive hideaway nestled beneath the bell tower. 2018 W. North Avenue.
Positioned above Millennium Park on the 13th floor of the Chicago Athletic Association, Cindy’s Rooftop commands some of the city’s most impressive vistas. Year-round terrace cocktails are available, though dining occurs indoors beneath the glass atrium. The establishment offers four distinct menus based on service time, all highlighting regional wild and seasonal ingredients. The Korean fried chicken sandwich from the lunch menu is absolutely essential. At dinner, the locally-sourced cheese and charcuterie board showcasing the chef’s curated selection of cheeses and cured meats provides an excellent meal opener. The extensive cocktail selection features both traditional and spirit-free options. The Raspberry Beret, combining Rittenhouse rye, Lustau Oloroso sherry with raspberry and hibiscus, deserves special mention. 12 S. Michigan Avenue.
Cabra, the indoor-outdoor dining destination atop The Hoxton, stands as the premier destination for ceviche. Executive Chef Stephanie Izardi’s Peruvian-influenced menu presents five ceviche varieties, from traditional preparations to shrimp, salmon, mushroom, and duck versions. The interior features soaring ceilings with expansive windows, a sophisticated teal color scheme accented with deep orange tones, wooden flooring, and abundant foliage. The outdoor terrace showcases a swimming pool alongside stunning city panoramas. For refreshments, the signature Pisco Sour or Pisco Fever—crafted with pisco, watermelon, lime, and tajin—make excellent selections. 200 N. Green Street.
The perfect setting for an elegant bubbly cocktail awaits atop Pendry Chicago, an architectural marvel resembling a champagne bottle with its distinctive green terra cotta exterior and gold-finished crown. Rising 24 stories above Michigan Avenue, this Côte d’Azur-inspired outdoor garden presents Lake Michigan and Chicago River views. Offerings include tarte au fromage, Maine lobster roll, and duck prosciutto. Weekend afternoons feature wood-fired pizza preparations. The French-leaning cocktail selection includes Bonjour, featuring Belvedere vodka, blueberry, vanilla, absinthe, and Fever-tree club soda. The French Sailor blends Captain Morgan rum, banana, Fever-tree elderflower, and absinthe foam. 230 N. Michigan Avenue.
Situated on the 18th floor of Viceroy Chicago, Pandan invites guests to enjoy cocktails and Southeast Asian fare while taking in expansive vistas of Lake Michigan and the charming Gold Coast neighborhood. The glowing blue pool illuminates the rooftop lounge during evening hours. The menu showcases pork lumpia, Thai fried chicken, and sweet corn tempura. The signature Red Panda cocktail merges Japanese whisky, turmeric, ginger, egg white, and pineapple. 1112 N. State Street.
Bar Avec radiates contemporary energy. Picnic tables, wicker hanging lights suspended overhead, and elevated seating delivering city panoramas recreate the casual elegance found in Spanish and Portuguese beach communities. Small plate selections maintain this Mediterranean aesthetic with offerings like scallops, steak tartare, and mussels. The beverage program highlights cocktails suited for summer warmth. Livin la Vinho Verde combines cucumber mint vodka with Ameal vinho verde, basil, and lemon, and those unfamiliar with orange wine should consider sampling a bottle. 640 N. Lasalle Drive.
For members and houseguests at Soho House, the rooftop experience is essential. This private sanctuary features striking black and white checkered paving, ambient string lighting, relaxation seating, and an ideal vantage point for admiring the urban landscape. The culinary offerings showcase abundant plant-based and gluten-free selections. The black truffle, squash blossom, and goat cheese pizza delivers exactly the refined experience the description suggests. 113-125 N. Green Street.
Housed on the fourth floor of The Godfrey Hotel Chicago, I/O Rooftop Lounge operates as a year-round rooftop destination offering expansive city views regardless of season. This adults-only venue features both sheltered and open-air sections, artisan cocktails, and abundant space accommodating groups, private functions, and evening celebrations. Weekend brunch service has become particularly popular. Advance booking is advised. 127 W. Huron Street
Commanding views of the Chicago River, LH Rooftop’s expansive three-tier terrace frames iconic vistas of Marina City and the Tribune Tower. The 22nd-floor terrace provides a relaxed ambiance with comfortable seating, high-top tables, and high-backed chairs. This New American restaurant’s menu emphasizes small plates and entrees sourced from regional farmers. Jamaican Jerk Wings arrive with pineapple pico and mango jerk glaze. The Mezze Plate offers an excellent vegetarian choice featuring hummus, baba ganoush, artichokes, roasted garlic, and pickled red onions. The Smoke Show—a margarita prepared with Casamigos mezcal, Casamigos blanco, guava, and lime—comes highly recommended. 85 E. Wacker Drive.
