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 11 secret and popular spots where you can get the most stunning Chicago skyline views.
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.
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. 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.
5. 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.
6. 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.
7. 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 the city’s 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.
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. T
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.
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. 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.
11. 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 11 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!
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?
