Chicago’s Best Sky Decks and Rooftop Restaurants For Date Night

Chicago River Skyline

Take Your Date Night to New Heights in Chicago

Chicago River Skyline

Chicago has always been one of America’s premier cities, known for its nightlife, trendy restaurants, great shopping, fine museums, and soaring skyscrapers.  While the city’s famous deep-dish pizza and hot dogs smothered in toppings may be perfect for a quick bite, when it comes to stepping out for the evening with your special someone, you will want to find some very cool things in Chicago.    We have found some amazing locations with fabulous views over the city to get your hearts pumping with excitement.  So come along on our tour of 6 of Chicago’s best Sky Decks and Rooftop Restaurants.

Willis Tower Sky Deck and The Ledge

The Ledge at Willis Tower Chicago
Wikimedia Commons by: Charlotte from Chicago

The highest observation tower in the United States is in Chicago at the Willis Tower Sky Deck and The Ledge.  This exhilarating experience gives visitors expansive views over the city that can span four states on a clear day.  Located on the 103rd floor, the experience includes the famous Ledge – a retractable 4′ glass balcony box that cantilevers out over the sidewalk 1,353 feet below!  Hold on to your loved one and take a leap of faith out over the streets of Chicago. This will get your hearts pounding for an unforgettable Instagram shot for sure!

360 Chicago – The Tilt at John Hancock Tower

The Tilt at John Hancock Tower Chicago
Flickr by: David Wilson

For a unique sky-high experience, zoom up to the 94th floor of the John Hancock Tower to experience The Tilt at 360 Chicago.  The tilt is an enclosed moving platform that tilts you out over famed Michigan Avenue.  Hold tight onto the grab bars, face forward and get ready as the floor tilts outward over the city.  There is also a nice bar and cafe and interactive learning opportunities for a great 360-degree experience above the streets of Chicago.

Centennial Wheel at Navy Pier

Centennial Wheel, Navy Pier, Chicago
Flickr by: Marcin Wichary

Chicago’s Navy Pier is a prime spot to spend a fun day or evening.  Its’ 50 acres are filled with fun attractions, free events, restaurants ranging from fine dining to take out, and shops galore, all on the picturesque shores of Lake Michigan!  No trip to Chicago is complete without a visit here.   The focal point of the pier is the towering 200′ Centennial Wheel, built to commemorate the 100-year (centennial) restoration of the pier.  Climb into one of the enclosed gondolas for a thrilling ride with 360-degree views of the city and waterfront.  With glass bottom floors, there is nothing to block the amazing scenes below and with heat in winter and air conditioning in summer, it’s always an exciting experience.

Terrace 16 at Trump International Tower

Trump Hotel Terrace, Chicago
Source: TrumpInternationalHotel

There’s no better spot for stepping out on the town for some glamorous pampering than a visit to the Trump International Tower Hotel; the 4th tallest building in the United States.  Top sites like CoolThingsChicago sing the praises of the hotel and Terrace 16.  Located on the 16th floor, you’ll discover an expansive rooftop restaurant and 200 seat patio cafe and bar.  The views over the river and Lake Michigan are exceptional as is the service and American cuisine.  Here you’ll experience a dramatic view with a dose of elegant pampering.

ROOF on theWit

Roof At The Wit, ChicagoSource:

Located on the 27th floor of theWit building, is one of Chicago’s most popular Bar, Lounge and Nightclub, simply called, Roof.  Being in the city center, the venue has sparkling skyline views from the terrace.  Visitors are greeted with chic decor, a retractable roof for any weather, and entertainment by celebrity DJs.  This is definitely one of Chicago’s IT places to be on a date night.

Apogee Lounge

Apogee Lounge is Chicago’s 2nd highest rooftop Bar and Nightclub, occupying the 26th floor of the Dana Hotel.  Furnishings are sleek and trendy with dramatic firepits and skyline views.  What sets Apogee apart from other sky-top lounges, are their extremely creative and impressive cocktails.  You’ll be amazed at the variety of drink concoctions as well as the unexpected containers they are served in.  An evening at Apogee is always a luxurious adventure.

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