11 of the Best Views in Chicago and Where To Find Them

Locals will still refer to Chicago’s tallest building as Sears Tower, but since 2009 this 10-story skyscraper has been renamed the Willis. No matter, as the vista from one of the coolest observation decks in Chicago—located in what was the tallest building in the world for 25 years—is as impressive as it’s always been.

Test your mettle on the Skydeck Chicago, where five ledge boxes provide you the opportunity to stand above nothing but a pane of glass with 1,353 feet (412 meters) of air between you and the sidewalk far below. On a clear day, you can even see four states and far across Lake Michigan from here.

Locals say Chicago is set on the “Third Coast” of the US. That’s because Lake Michigan is so expansive, and dominates the geography of the city, that it really does feel like it’s an ocean. From the lake itself, you can see how the city hugs the shore and stretches north and south—highlights include the mansions along Lake Shore Drive and the modernist architecture of The Magnificent Mile.

There are watery experiences for every taste: from a private sailboat charter to a speedboat ride that may leave you more focused on keeping your lunch down than where to see the best sights in Chicago. Or consider renting a kayak and exploring the coast at your own pace. Just watch out for those speedboats!

Chicago is blessed with world-class green space in the middle of the city. From the north, near the Art Institute, check out the world-famous Cloud Gate sculpture (more familiarly known as The Bean), which forms the centerpiece of Millenium Park. Just to the east is Maggie Daley Park, home to an ice rink in winter. Then, walk south past Buckingham Fountain in Grant Park. All of these locations, which together form around 319 acres (129 hectares) of public parkland, offer varied views of the Loop’s skyline (and serve up unmatched opportunities for photos). The only better view of the heart of downtown is from the seat of a helicopter.

An architecture tour along the Chicago River is a must-do in Chicago with good reason. In just a few miles, you witness more than a century of architecture—from the neo-Gothic Tribune Tower to the midcentury Marina City towers (aka the corn cob buildings) to the new St. Regis Chicago, a hotel that features an undulating glass exterior. Make sure the guided river cruise you select explores all three branches of the waterway, such as one aboard the Lady Liberty. You may have a crick in your neck by the end from staring upward, but you’ll leave with an appreciation for the incredible density of architectural wonders in the city.

Continue south from Grant Park and you’ll hit the Field Museum, behind which a large spit of reclaimed parkland called Northerly Island juts out into the lake. Because this human-made island is set out from the rest of the shoreline, it features some of the best Chicago skyline views. It’s also a great place to get away from the bustle of the city, and it often hosts music festivals and other events. One highlight is the Adler Planetarium, at the northern end, which was the country’s first such building. But the real draw is the fact that Northerly is an urban nature preserve, with 150 species of native plants and various walking and biking trails.

Some of the best views in life are cheap. The “L” is Chicago’s partially elevated (get it?) metro system. In the Loop, you’ll be hard pressed for a good view—many of the lines run right next to the skyscrapers, which is a unique experience in itself. Instead, ride the Pink Line into West Town and popular Fulton Market, or continue into Pilsen, a predominantly Mexican-American community area, which is a great neighborhood to explore with the help of a walking tour. The trip back and forth will feature panoramic views of Chicago.

Stephanie Izard is a Chicago culinary star who started a revolution in the city’s restaurant scene after becoming the first woman to win Top Chef in 2008. She now operates five restaurants in the city, all of which are worth visiting, but Michelin-rated Cabra should be your first stop. There’s no shortage of rooftop bars with a view in Chicago, but this Peruvian restaurant and bar features a rooftop that’s classy yet unpretentious. Kick back with an order of ceviche and a pisco sour and watch the skyline, the nearby L trains, and the hip crowd of diners.

A favorite for students from the University of Chicago, Promontory Point juts out from the area of Hyde Park into Lake Michigan. When it’s warm enough, lounge on the large limestone slabs leading into the lake, or bring food for an impromptu picnic on the grass above. The views are of course the highlight, as downtown Chicago’s buildings curl around the shore at a distance, and the Point’s design ensures 360-degree visibility. Ambitious visitors may want to make use of the Lakefront Trail by biking the 7 miles (11.3 kilometers) from downtown, and once you’re in Hyde Park make sure to see one of Chicago's architectural must-sees: the Robie House designed by Frank Lloyd Wright.

Chicago’s answer to New York City’s High Line, the 606 (also known as the Bloomingdale Trail) is a former elevated train track that the city converted into a multi-use path in 2015. It runs between the neighborhoods of Humboldt Park in the west and Wicker Park in the east, a distance of 2.7 miles (4.3 kilometers)—longer than its cousin in the Big Apple, by the way. Set along the path are different scenic viewpoints, which look onto expansive Humboldt Park, the Logan Square neighborhood, and downtown. Once you’re done, explore the diversity of the rest of the West Town area, which highlights the Ukrainian and Polish heritage of Chicago.

Walking through Palmisano Park, in the neighborhood of Bridgeport, you are treading over epochs of history. That’s because the area millions of years ago was a coral reef, samples from which now call the Field Museum home. In more recent centuries, the area has been a quarry and then a landfill, before finally becoming a park. The reason it’s on the list, though, is that the so-called “summit” of the park is one of the most scenic spots in Chicago, and locals use it as a place for picnics and other gatherings.

Insider tip: A trip to Bridgeport is also a great excuse to explore more South Side neighborhoods, such as Bronzeville or Back of the Yards. The best way to do so is a tour led by a local expert.

About an hour’s drive outside the city, Indiana Dunes National Park offers a relaxing getaway and some of the best views of Chicago. Take the Dune Succession Trail from the West Beach trailhead, which includes 270 stairs and tracks different stages of how dunes develop over time. Then, from the beach itself, spot Chicago’s iconic buildings—around 28 miles (45 kilometers) away as the bird flies. It’s one of the best and least-known Chicago skyline photography locations, especially in the evening, when the setting sun can backlight the skyscrapers.