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Chicago's Best Sky-High Views: Top Observation Decks & Rooftop Bars

Looking for the best views of Chicago? From observation decks soaring 1,000 feet in the air (like Skydeck Chicago or 360 CHICAGO) to rooftop bars with sweeping skyline views, we’ve compiled five of our favorite ways to see Chicago from above.

Observation decks

Chicago s Best Sky-High Views: Top Observation Decks & Rooftop Bars

When it comes to the best views in Chicago, it’s hard to beat the city’s dramatic observation decks. Take a trip up 103 floors to Skydeck Chicago, located atop the Willis Tower, where you’ll find a thrilling feature: The Ledge. This glass-floored observation box takes you 1,353 feet over the street, offering unparalleled views (and an adrenaline rush!). Meanwhile, 360 CHICAGO (formerly the John Hancock Observatory) unveiled exciting enhancements to its guest experience and observation area, making it the perfect spot to watch the sunset. Venture up 94 floors to the observation deck, and relax in stadium-style seating overlooking the Chicago skyline, or grab a cocktail and a bite to eat in the new cafe and bar while taking in spectacular views.

Rooftop bars and restaurants

Chicago s Best Sky-High Views: Top Observation Decks & Rooftop Bars

Want to enjoy a delectable drink with your view? Check out one of the many rooftop bars in Chicago. For something new and noteworthy, head up to the roof at Chicago Athletic Association — the trendy boutique hotel that opened in a historic 1890s athletic club — to check out Cindy’s, a New American restaurant with an open-air terrace overlooking lush Millennium Park.

For an urban rooftop tucked amid glass-walled skyscrapers and overlooking the bustle of downtown, Streeterville Social atop Loews Chicago Hotel offers the perfect vantage point, as well as a grassy lawn area for playing games. For a funky, colorful space with a party vibe, try the plush, outdoor lounge area at Cerise, located on the roof of Virgin Hotel Chicago, located in the heart of the Loop.

Insider tip: Explore more Chicago rooftop bars and patios.

Navy Pier Ferris wheel

Chicago s Best Sky-High Views: Top Observation Decks & Rooftop Bars

Navy Pier has a number of iconic attractions, but perhaps the most memorable is its behemoth Centennial Wheel, the 196-foot Ferris wheel that replaced the previous one in 2016. Take a ride up and be ready with your camera. The lake is a beautiful blue expanse and the downtown skyline spreads out alongside it. Below, the colorful lights from the Pier Park rides entertain the masses. For the daring, pay for the upgrade to the glass-bottomed VIP Premium Gondola.


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