Plan to do some sightseeing in Chicago with these things to do — with a view! Skyscrapers are your backdrop when you have a nightcap at these Chicago rooftops. And the busy city streets look tiny below when you travel up to The Skydeck or 360 Chicago. Bring your camera and Instagram away at these 5 top Chicago sightseeing stops!



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 The Skydeck, 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) recently 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.


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. For even more great places to eat in Chicago, check out one of these alfresco dining spots with a view.


Rustic yet sophisticated Italian cuisine is on the menu at the newly renovated Cafe Spiaggia, where an airy, light-filled dining room features sleek light fixtures, marble tables, black chairs, white leather banquettes, oversized windows and dramatic views of Lake Michigan. Meanwhile, at the The J. Parker atop Hotel Lincoln, New American small plates are served up in a solarium-style dining room, offering unobstructed views of Lake Michigan and as a bonus, a year round glass rooftop to keep warm in the winter. At The Kitchen, nosh on farm-to-table fare in a bistro-style dining room with windows overlooking the Chicago River. 


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.


Want an incredible view and something to check off your bucket list? Vertiport VIP Helicopter Tours offer a once-in-a-lifetime Chicago experience. Choose from a variety of premier options, including fireworks tours, holiday lights tours, pilot experiences, and romance packages. Or go above and beyond with a custom tour just for you. 

Or, soar above the Chicago skyline with a Chicago Helicopter Experience tour. Book a daytime tour, and learn all about the city's history and landmarks or try a twilight tour to watch the sunset light up the sky. The nighttime tour showcase the city lights from above for a breathtaking experience.


Related Listings

360 CHICAGO (formerly John Hancock Observatory)
875 N. Michigan Ave.
Chicago, IL 60611
(888) 875-8439

Skydeck Chicago
233 S. Wacker Dr.
Chicago, IL 60606
(312) 875-9696

Hotel Lincoln
1816 N. Clark St.
Chicago, IL 60614
(312) 254-4700

Virgin Hotels Chicago
203 N. Wabash Ave.
Chicago, IL 60601
(855) 946-6600

The Chicago Athletic Association Hotel
12 S. Michigan Ave.
Chicago, IL 60602
(312) 940-3552

Navy Pier
600 E. Grand Ave.
Chicago, IL 60611
(312) 595-5300

Café Spiaggia
980 N. Michigan Ave.
Chicago, IL 60611
(312) 280-2750

Chicago Helicopter Experience
2420 S. Halsted St.
Chicago, IL 60608
(855) 414-8687

Loews Chicago Hotel
455 N. Park Dr.
Chicago, IL 60611
(312) 840-6600

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