Chicago, a city renowned for its stunning architecture, world-class museums, and deep-dish pizza, offers another incredible way to experience its beauty: from above. As the weather warms up, the city's rooftops transform into chic oases, offering breathtaking views, creative cocktails, and delicious food. Rooftop dining in Chicago combines the city's vibrant culinary scene with its iconic skyline. These elevated spaces provide a unique perspective, allowing you to dine among skyscrapers and watch the bustling city from a peaceful perch. Let's talk about some of Chicago's most stylish rooftop restaurants, from lively spots in River North to sophisticated escapes in the West Loop.

River North: The Epicenter of Rooftop Glamour

The River North neighborhood is the heart of Chicago's entertainment district, boasting a high concentration of upscale restaurants, galleries, and buzzing nightlife. It's no surprise that this area is also home to some of the city's most popular and chic rooftop bars.

Cindy's Rooftop

Perched atop the historic Chicago Athletic Association hotel, Cindy's Rooftop is arguably one of the most famous rooftop spots in the city. Its main draw is the jaw-dropping, unobstructed view of Millennium Park, "The Bean" (Cloud Gate), and Lake Michigan. The space itself is stunning, with a design that feels like a bright, airy greenhouse with a large outdoor terrace.

Cindy's is known for its creative, large-format cocktails that are perfect for sharing with a group. The menu features seasonally inspired American cuisine with an emphasis on fresh, high-quality ingredients. Due to its immense popularity, it can get very crowded, especially on sunny days and weekends. Reservations for dinner are highly recommended. For a more casual experience, you can try visiting on a weekday afternoon to enjoy the view with fewer people.

Aba

Located in the historic Fulton Market district, Aba offers a Mediterranean-inspired escape that feels miles away from the city. The name means "father" in Hebrew, and the restaurant is a sibling to the popular Ema in River North. The rooftop patio is a lush, green oasis filled with trees, plants, and comfortable seating, creating a warm and inviting atmosphere.

Aba's menu focuses on the flavors of Israel, Lebanon, Turkey, and Greece. You'll find delicious mezze like smoky garlic hummus, crispy short rib hummus, and whipped feta spread. The cocktail program is equally impressive, with drinks that incorporate Mediterranean spirits and spices. Aba's combination of a beautiful, garden-like setting and flavorful food makes it a perfect choice for a sophisticated yet relaxed rooftop dinner or brunch. Reservations are essential as this is one of the most sought-after spots in the city.

The West Loop: Trendy and Food-Focused

The West Loop has transformed from an industrial meatpacking district into Chicago's hottest culinary destination. This neighborhood is known for its innovative, chef-driven restaurants, and its rooftop scene is no exception.

Cabra

Located on the top floor of The Hoxton hotel, Cabra is a vibrant Peruvian-inspired restaurant from celebrated chef Stephanie Izard. The rooftop space is bright and colorful, with a lively atmosphere and fantastic views of the West Loop skyline. There's an indoor dining room with floor-to-ceiling windows and a beautiful outdoor terrace with a pool.

The menu is a fun and approachable take on Peruvian cuisine, featuring a variety of ceviches, skewers (anticuchos), and other shareable plates. The dishes are packed with bold, bright flavors. The cocktail list is equally playful, with a focus on pisco, Peru's national spirit. Cabra's energetic vibe, delicious food, and great views make it a top choice for a fun night out with friends.

VU Rooftop Bar

Situated on the 22nd floor of a building in the South Loop, near the West Loop, VU Rooftop Bar offers a unique and spectacular perspective of the Chicago skyline, including clear views of Willis Tower and the lake. The space is massive, with 13,000 square feet divided into indoor and outdoor areas, complete with multiple bars and cozy fire pits.

VU offers a more relaxed, lounge-like atmosphere compared to some of the high-energy spots in River North. The menu consists of elevated bar bites and shareable plates, making it a great place to gather for drinks and a light meal. The impressive scale of the space and its unique vantage point make it a standout option for anyone looking to be wowed by the city lights.

The Magnificent Mile: Shopping and Sky-High Sips

The area around Michigan Avenue, also known as the Magnificent Mile, is Chicago's premier shopping district. After a day of retail therapy, there are several chic rooftop spots where you can relax and take in the views.

Z Bar

Located in The Peninsula Chicago, one of the city's most luxurious hotels, Z Bar is a sophisticated and globally inspired rooftop lounge. The terrace offers stunning views looking down the Magnificent Mile. The atmosphere is upscale and refined, making it an ideal choice for a special occasion or an elegant evening.

Z Bar is renowned for its world-class cocktail program. The menu takes you on a journey around the world, with expertly crafted drinks featuring rare spirits and unique ingredients. The food menu is composed of artfully presented small plates from different culinary traditions. It’s a place to indulge in luxury and enjoy some of the best-made drinks in the city.

LondonHouse Rooftop

The rooftop at LondonHouse Chicago is famous for its multi-level design and absolutely iconic views. Spanning the top three floors of the hotel, it offers breathtaking panoramas of the Chicago River, the Michigan Avenue bridge, and the surrounding architectural gems like the Tribune Tower and the Wrigley Building.

The main 22nd-floor terrace is a sprawling, lively space, while the 23rd-floor cupola offers a more exclusive, intimate setting (often reserved for private events). The bar serves classic cocktails and a menu of American fare. Because of its prime location and incredible photo opportunities, LondonHouse is extremely popular. Be prepared for crowds, but the view is undeniably one of the best in Chicago.