The 16 most stunning Chicago skyline views

It's no secret that the flagship parks of downtown Chicago—namely Grant and Millennium—are home to some pretty stunning views of the skyline. To get a more novel downtown perspective, though, try visiting the Lurie Garden. Tucked into the southern end of Millennium Park, its verdant expanses of wildflowers and grasses make an extra-appealing foreground for the city skyline.

If you don't have the time to hop on a boat tour, strolling along the Riverwalk is an easy way to see Chicago's finest architecture from a new angle. Buildings tower far above you on either side, and there are plenty of places to sit down and take in the scenery.

Although it’s often labeled a tourist trap, Navy Pier actually has plenty to offer to both locals and out-of-towners alike. Head to Offshore for the world’s largest rooftop bar and sweeping, unobstructed views of the city’s towering skyscrapers. If you're looking for spectacular sights from up high, take a ride on the Centennial Wheel—a 200-foot-high Ferris wheel with enclosed, climate-controlled gondolas.

A view worth missing your train for? Believe it. If you've ever transferred at the Ashland Green and Pink Line stop, you've likely had a chance to take in the amazing, unobstructed perspective of the skyline from the station's elevated crossing over the tracks. It's arguably the most comprehensive view of Chicago's architecture on the West Side (and the city in general).

The most obvious place to catch a great view of Chicago is on the 103rd floor of the city's tallest building. Since the Willis Tower added The Ledge, which suspends guests in a glass box 1,353 feet in the air, the attraction offers about as good of a view as you're going to get anywhere in the country, aside from an airplane.

Taking a bike ride or a stroll along the lakefront by the Adler Planetarium is a great way to see the city. The museum sits just north of Northerly Island in a spot that juts out into the lake east of South Loop—and when the light and water conditions are just right, you can catch a view of the skyline reflecting onto the lake.

Walking along the northern end of Belmont Harbor explains why Lake Michigan is a Great Lake—when you hit the edge of the water it feels like you've reached the edge of the Earth. If you're on the North Side and looking for a happy place, this is a sure bet.

Lincoln Park is full of attractions, but after you've finished scoping animals at the zoo, try looking toward the horizon for incredible skyline vistas—the whole park is bursting with them. Just as an example, you can head over to the South Pond, where the city's buildings pop up above the trees, contrasting urban monoliths with natural flora.

Originally a railroad yard, Chinatown's Ping Tom Park is now home to 12 acres of rolling green space and riverfront paths with picturesque views of the skyline facing north. For an even clearer vantage point, climb up to the 18th Street Bridge, where you can soak in views of both the cityscape and the historic St. Charles Air Line Bridge.

The Chicago Athletic Association’s beach house-inspired rooftop restaurant is always one of the hottest destinations in the city and it’s not hard to see why. Perched on the 13th floor, Cindy’s boasts an open-air terrace that offers panoramic views of the skyline, lake and Chicago’s front yard—Grant Park. Grab a craft cocktail to sip on and battle the crowds for a picturesque selfie; we promise it’s worth the effort.

Named after U.S. veteran Milton Lee, this park located on a man-made peninsula in Lake Michigan is a gem that’s hidden in plain sight. Pack a picnic to enjoy while you lay out and take in breathtaking views of the skyline. You may even catch a picturesque wedding proposal in progress.

We know the former site of the Meigs Field airport is great for catching a concert, a leisurely stroll or some fishing, but the peaceful patch of land also offers breathtaking views. It’s surreal to stand in the middle of this serene grassy area and see a majestic city towering on the horizon. 

Some of the best skyline views on the South Side can be found at Palmisano Park in Bridgeport, a former limestone quarry turned peaceful park in 2009. Scale the hill locals call “Mount Bridgeport” on a sunny day for a stunning panorama.

Tucked away along the lakefront in Hyde Park, the views from Promontory Point demonstrates just how huge Chicago's skyline really is. It's more than seven miles away from the Loop, but the buildings still look as looming and stately as ever.