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Home » Where to See the Best Chicago Skyline Views: Uncover Top 13 Viewing Spots With a Local

Where to See the Best Chicago Skyline Views: Uncover Top 13 Viewing Spots With a Local

Chicago skyline view from the lakefront

Chicago, the third-largest city in the United States, remains an underrated travel destination. International tourists often flock to the streets of New York or the coastal cities of California and miss out on this beautiful Midwestern gem. A visit to Chicago is sure to stimulate your intellect, inspire your creativity, and calm your energy with its museums, art, theatre, lake, and parks. And of course the incredible Chicago skyline views.

I feel fortunate to have called this city home for 12 years and I’m excited to cover more of my city on this blog. Oftentimes, the best experiences lie in our own backyards. Every time I have a friend or family member visiting Chicago for the first time, I realize how much there is to see and do in the city.

One of the main things Chicago is famous for is its architecture. Art Deco, Gothic, Victorian, mid-century modern, and post-modern are all architectural styles to be found in the city of Chicago. There is nothing more satisfying than seeing a combination of these buildings against the backdrop of the vivid blue sky and ever-changing waters of Lake Michigan. Here is a mix of 13 secret and popular spots where you can get the most stunning Chicago skyline views.

Myself posing in front of the Chicago skyline in Milton Lee Olive Park
View of Chicago skyline from Milton Lee Olive Park

1. Milton Lee Olive Park

Tourists swarm to the popular attraction Navy Pier but often miss this “hidden in plain sight” gem just north of the pier. As you walk along the park promenade bordering Lake Michigan, you get a clear view of the Chicago skyline in the north with the familiar horns of the John Hancock Center (now 360 Chicago), the curvy Lake Point Tower Condominium, and everything else in between.

There’s even a fantastic triangular viewpoint that, when you stand at one of its corners, makes you feel as if you are sailing above the water. This is a great spot for pictures of you in the foreground with the best of Chicago – an impressive skyline and a Great Lake.

I love taking out-of-town family and friends to this park in the summer during their Navy Pier visit. They are pleasantly surprised and we end up spending a lot of time just walking next to the lake, watching a wedding photoshoot, or plopping ourselves on the grass admiring the best Chicago skyline views.

2. Diversey Harbor

Diversey Harbor offers a stunning view of the Chicago skyline from its vantage point in the northern neighborhood of East Lakeview. The harbor’s location along Lake Michigan provides an unobstructed view of the city’s iconic skyscrapers, including the John Hancock Center, the Willis Tower (formerly known as the Sears Tower), and the Trump International Hotel and Tower to the south.

The AIDS Garden that opened last year provides the perfect entryway to the harbor. It is a very dramatic sight when you walk through the garden and suddenly see the lake’s blue expanse. Continue walking south on this harbor and you will be rewarded with everchanging views and moods of Lake Michigan. As you round the curve near the blue Chevron statue, the best Chicago skyline view enters your line of sight along with a view of the beaches along the way and a glimpse of Navy Pier to the left.

Two people on a standup paddleboard in Lake Michigan against the Chicago skyline backdrop
Chicago skyline view from Diversey Harbor

3. North Pond

North Pond is a freshwater lake located in Chicago’s Lincoln Park neighborhood. It is surrounded by lush greenery and provides a peaceful and scenic escape from the city. The lake is popular among bird watchers and nature enthusiasts, as it is home to a variety of waterfowl, including ducks, geese, and swans, as well as other wildlife such as beavers and muskrats. I’ve also spotted a turtle every once in a while near the waters of North Pond.

You can enjoy one of the best Chicago skyline views from the clearing near the North Pond restaurant. The views of the lake, surrounded by the towering trees and cityscape in the background, provide a unique and picturesque juxtaposition between nature and the urban environment.

4. Ping Tom Memorial Park

Ping Tom Memorial Park is located in the Chinatown neighborhood of Chicago, and it offers a unique and picturesque view of the city’s skyline. From the park, you can enjoy one of the best Chicago skyline views against the backdrop of the Chicago River.

I was here with my out-of-town friend just last week and she agreed that this was one of the best Chicago skyline views. The contrast between the natural beauty of the river and lush greenery against the urban landscape of skyscrapers here makes this one of my favorites on this list. You’ll see the Chicago River flowing gently, with boats and kayaks passing by, and then towering above it, you’ll see the impressive buildings that make up the city’s skyline.

The pagoda makes for fantastic photo ops and we saw at least two bridal photo shoots in the park. But don’t just stop at the pagoda. Keep walking north along the river toward the downtown skyline and you’ll come across a red-rail walkway that offers just the right pop of color in the foreground for all your Instagrammable pictures.

Pro tip: Take the water taxi from Ping Tom Memorial Park to Union Station when it’s running. It will be the best $10 you spend. The taxi takes about 15 minutes and slowly moves towards the skyline giving you several moments to pause and appreciate the beauty all around. You can also take the longer one to Michigan Ave for $19 if you’d like to hang out longer in the water.

Best Chicago skyline view with red walkway and bridge from Ping Tom Memorial Park
Best Chicago skyline view from Ping Tom Memorial Park

5. Honeycomb at Lincoln Park

The “Honeycomb” in Lincoln Park, Chicago is a sculpture created by artist Jean Dubuffet. The artwork is a large, abstract form made of concrete and steel, and is part of the park’s public art collection. The sculpture is known for its unique, honeycomb-like pattern, which creates a distinctive, textured surface.

One of the best Chicago skyline views is visible when you stand at the northern end of the Honeycomb and look towards the south. The sculpture arc frames the top of the view with antennas from John Hancock Center and Trump Tower among other residential skyscrapers.

6. North Ave Beach Pier

North Avenue Beach in Chicago is a popular public beach located along Lake Michigan, near the Lincoln Park neighborhood. The beach is known for its spectacular views of the Chicago skyline, particularly the iconic skyscrapers along the city’s famous “Magnificent Mile”. From the beach, visitors can enjoy a panoramic view of the city, including landmarks such as the John Hancock Center, the Willis Tower (formerly known as the Sears Tower), and the Trump International Hotel and Tower.

The North Avenue Beach Pier, located at the end of the beach, provides an even more elevated view of the skyline and the lake. The pier is a popular spot for photography and sightseeing and is also used for fishing and other recreational activities. Visitors can enjoy the views from the pier, or take a walk along the lakefront path for additional perspectives of the city and its skyline.

View of iconic Chicago skyscrapers behind Lake Michigan
Chicago skyline view near North Avenue Pier

7. TILT at 360 Chicago

360 Chicago, formerly known as the John Hancock Observatory, is an observation deck located on the 94th floor of the John Hancock Center in Chicago. The deck offers 360-degree views of the city, including the Chicago skyline and its many iconic skyscrapers. From the observatory, you can see the city in all directions, including the nearby lakefront, parks, and neighborhoods.

In addition to the breathtaking views, 360 Chicago also offers several interactive exhibits and multimedia displays that provide information about the city’s history, architecture, and culture. But the main attraction here is TILT which literally lets you tilt over the city from 1,030 feet above. Keep in mind that weather and particularly the wind may render the TILT to be closed temporarily. So pick a beautiful day in summer, late spring, or early fall for the best experience.

8. Chicago Architecture River Cruise

If there is one popular tourist activity that is also loved by the locals, it is the Chicago Architecture River Cruise. The cruises offer a unique perspective of the city and its architecture, allowing visitors to see many of its iconic skyscrapers, bridges, and historic buildings from the water.

The cruises, operated by multiple companies, provide an in-depth narration of the architectural styles like Art Deco, Gothic and mid-century modern that are on display all around you. You’ll hear the stories behind the buildings like Willis Tower, Merchandise Mart, Tribune Tower, and Wrigley Building.

For a truly magical experience, book a golden-hour cruise. There is a particular point during the cruise where you can grab a shot of one of the best Chicago skyline views. The boat moves along the river and finally enters the lake and pauses for a few minutes where you can turn around to see a spectacular display of the city’s iconic skyline.

Silhouette of skyscrapers against the setting sun by the Chicago River
Chicago skyline view during sunset on the Architecture Cruise

9. Adler Planetarium Skyline Walk

Adler Planetarium is a world-renowned science museum, dedicated to exploring the wonders of the universe and promoting public understanding of astronomy and space science. And it is on the doorsteps of this planetarium that you can see one of the best skyline views of the Windy City. The planetarium is part of Chicago’s Museum Campus which also houses the Shedd Aquarium and the Field Museum.

Walk westwards along the lakefront trail on the doorsteps of Adler Planetarium for a stunning view of the city’s skyline including the multi-layered Sears Tower, the slanting top of the Crain Communications Building, and the glass exterior of the Shedd Aquarium.

10. Centennial Wheel at Navy Pier

The Centennial Wheel at Navy Pier was installed in 2016 as part of Navy Pier’s 100th-anniversary celebration and stands at a height of 200 feet (61 meters). The wheel offers panoramic views of Lake Michigan, the Chicago skyline, and the surrounding area.

The Centennial Wheel features climate-controlled gondolas that provide a comfortable and enjoyable experience, even in inclement weather. The ride lasts for about 15 minutes with the gondolas moving at a slow speed so you aren’t rushed to capture the best Chicago skyline views.

Ferris wheel overlooking the Chicago skyline, harbor and park
Mid-air view of the Chicago skyline from the Centennial Wheel in Navy Pier

11. Promontory Point

Located at the tip of a peninsula in the Hyde Park neighborhood, Promontory Point provides a panoramic view of the city’s beloved skyscrapers. The point is also a popular spot for picnics featuring a large, grassy area, several picnic tables, and a wide concrete terrace that provides ample space for you to enjoy the views and the surrounding park.

You can use this spot as a jumping-off point for exploring the rest of the Hyde Park neighborhood in South Side Chicago. The culturally rich neighborhood is home to the University of Chicago, the Museum of Science and Industry, and the UNESCO World Heritage Site – Frank Lloyd Wright’s Robie House. Don’t forget to visit Obama Kissing Rock, the site of the old Baskin Robins ice cream parlor where Barack and Michelle Obama shared their first kiss.

12. Buckingham Fountain

The Buckingham Fountain is an iconic landmark located in Grant Park in downtown Chicago. It’s situated in the center of a large plaza, and the fountain itself is quite grand and ornate. The fountain features a central jet that shoots water up to 150 feet into the air, along with smaller jets and a stunning light show at night.

From the plaza surrounding the fountain, you’ll have an unobstructed view of the city’s skyline to the northwest. Circle the fountain before grabbing a seat on one of the benches on the southeast side of the plaza. This gives you a front-row seat to one of the best Chicago skyline views with the beautiful fountain in the foreground flanked by iconic buildings like Willis Tower, John Hancock Center, Crain Communications Building, and others in the background.

View of Buckingham Fountain against the Chicago skyline
Best Chicago skyline view from Buckingham Fountain Plaza

13. Skydeck

The Skydeck, located on the 103rd floor of the Willis Tower, offers stunning views of the Chicago skyline. You can step out onto The Ledge, a series of glass balconies extending 4.3 feet from the building, for a truly breathtaking experience.

There’s something special about feeling like you are suspended in mid-air and watching the city’s beautiful skyline from above. On a clear day, you can even see as far as the states of Indiana, Wisconsin, and Michigan from here. Choose the day or night view, or better still head there in the late evening just before sunset. You can watch the scene transform from pinkish-blue skies to a city twinkling in yellow and orange as night begins to fall.

And that my friends, is a curated list of the 13 best Chicago skyline views. I’ve tried to include some of the popular attractions like Skydeck and River Cruise but have focussed more on local favorites like Milton Lee Olive Park, Lincoln Park’s Honeycomb, and Promontory Point.

A view of the Chicago skyline never gets old. It is a testament to the resilient spirit of the city which was almost destroyed by the Great Fire of 1871. As you move through these skyline attractions, take your time to pause and enjoy the city’s diverse cuisine, lush greenery, and seasonal beauty. It’s easy to see why Chicago has topped the Condé Nast Traveler Readers’ Choice list of Best Big City in the U.S. not once or twice but SIX times!

Best Chicago skyline view from the skydeck
View of Chicago skyline from skydeck

If you’re a Chicagoan, I’d love to hear your favorite spots to watch the city’s skyline. And if you are planning a visit to Windy City, which of these places are you most excited to check out?

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