It’s only been a few years since I moved to Chicago, and I am still amazed at how incredibly vast the city looks when standing at a distance. The Chicago city skyline is a marvel to behold during the day or at night. If you are new to the city like I was and are looking for the ideal spots, here are my top places to see the Chicago skyline.
1. Outside Alder Planetarium
At the Alder Planetarium, you can see the stars and the skyline. This spot is close to the Shedd Aquarium and Museum Island, so plenty of parking is nearby. It’s a great location because you can see a completely unobstructed view of the city.
I remember the first time I saw the Alder Planetarium. My goal was to photograph the sunrise, as many Chicago photographers do. I wake up extra early to drive down to the city. There was one problem I just remembered: I needed to check the weather. It is icy outside. The kind of cold that chills to the bone. My recommendation is not to go on cold days because the wind chill by the lake will not put you in any mood to take photos.
Nevertheless, I pulled into the street parking, which was free before 7 a.m. on Sundays, and got my camera gear ready. I moved quickly and grabbed a few shots before running back to the car. Seeing the skyline at sunrise for the first time was breathtaking.
Since then, I have been back to this spot several times- never as cold as the first time.
2. North Avenue Beach
In the summer, North Avenue Beach is full of visitors soaking up the sun, playing volleyball, and dipping their toes into Michigan Lake. Myself being one of those visitors. Last summer, I discovered how incredible North Avenue Beach is. It’s the ideal place to walk or dive into Lake Michigan.
North Avenue Beach is close to the Gold Coast and Michigan Avenue. It is open from 11 a.m. to 7 p.m. on Fridays before Memorial Day through Labor Day.
3. Lincoln Park Zoo
The Lincoln Park Zoo is home to nearly 200 different animals and is completely free to the public. You can visit the polar bears and penguins and see fantastic views of the city skyline. One of my favorite city skyline views can be seen along the Lincoln Park Zoo Nature Walk.
4. Montrose Point Bird Sanctuary
Before it got shut down, I participated in Friday Swim Club. Every Friday, the Friday Swim Club jumps into Lake Michigan before work. It takes place at Montrose Point Bird Sanctuary. You can walk, run, or just sit and enjoy the view with waves crashing below. Montrose Beach is both peaceful and picturesque, with some of the best views of the Chicago city skyline. You are a little further away but I find it to be very peaceful- especially in the morning.
5. Navy Pier
Navy Pier is famous for its iconic Ferris wheel, which offers views of the Chicago skyline. Even if heights aren’t your thing, the Pier is a fantastic spot to enjoy ground-level city views. It’s also a popular place for special moments—like proposals! In fact, my cousin got enaged there, and I had the honor of capturing the moment on camera.
6. Cindy’s Rooftop Bar
If you visit Chicago, especially in the summer, rooftop bars are a great way to see the city skyline and grab a cocktail. Until other cocktail bars, Cindy’s Rooftop offers a great view of both the bean and the city skyline. If you are wanting to grab a drink around Millinuim Park this is the ideal location.
7. The Willis Tower (4th floor & Skydeck)
The first time I visited the Willis Tower, I found a hidden gem. Not knowing where the line for the Willis Tower Skydeck began, I took the elevator to the fourth floor. The space has lounge chairs and tables 360 views of the skyscraper and is always empty- making it a perfect spot to relax and enjoy the scenery.
The Skydeck is where you can enjoy some of the best bird’s-eye views of Chicago. The first time I visited, I didn’t have time to wait in line for the primary Skydeck experience, which usually requires purchasing tickets in advance.
8.) The Wrigley Building
The Wrigley Building is a stunning spot to view the Chicago skyline, offering a perfect blend of iconic architecture and the picturesque river in a single photo. This is one of my favorite spots to take wedding photos. See my full gallery here.
9.) North Rose Garden
The North Rose Garden is my best-kept secret for taking beautiful wedding photos in the city with minimal crowds. This garden is perfect if you want some Instagram photos in the city. There are minimal crowds, and the views of the city are incredible.
10.) Top of the Art Institute of Chicago
If you are making a stop by the Art Institute of Chicago on your visit to Chicago, don’t miss out on the rooftop views.
11.) Ping Tom Park in Chinatown
Ping Tom Park in Chinatown, Chicago, offers some of the most stunning views of the city skyline, making it a favorite destination for locals and visitors alike. Nestled along the Chicago River, the park features beautifully landscaped gardens, a striking pagoda-style pavilion, and serene walking paths that perfectly frame the cityscape, especially at sunset. Not only that, but it is home to some of the best food in the city.
12.) Chicago Riverwalk
When having a day in the city, I love walking the Chicago Riverwalk and taking in the views of the skyscrapers and water.
13.) Starbucks Reserve
The largest Starbucks in the country happens to be in Chicago. This giant Starbucks, also known as the Starbucks Reserve, has four floors. If you get a window view the Starbucks Reserve has some of the best views of Michigan Ave.
14.) Milton Lee Olive Park
Milton Lee Olive Park offers unparalleled views of the city’s iconic skyline. Located just north of Navy Pier along the lakefront, the park provides a serene escape from the bustling city, with its expansive lawns, shaded walking paths, and fountains. Its unique vantage point allows visitors to see the skyline reflected against the tranquil waters of Lake Michigan, creating a picturesque scene that feels almost cinematic. The park’s design, with its open spaces and thoughtfully placed benches, invites you to linger and take in the panoramic views of towering skyscrapers like the Hancock Center and the Willis Tower.
15.) Top floors of the Merchandise Mart
You can’t miss the Merchandise Mart while walking past the Chicago Riverwalk. It is a gigantic art deco building built in the 1930s. Many interior design stores operate out of the building.
16.) Monroe Harbor at Shedd Aquarium
The Shedd Aquarium is one of the largest aquariums in the United States. It has over 25,000 fish, marine mammals, birds, snakes, amphibians, and insects. While the Shedd Aquarium is a great spot to visit, just outside of the aquarium, it has some of the best views of Lake Michigan and the city behind it.
17.) 18th Street bridge
Spanning the South Branch of the Chicago River, this bridge offers a unique, elevated perspective that frames the iconic skyscrapers against the river’s reflective surface. Its location near Pilsen and Chinatown is steeped in the vibrant culture of the surrounding neighborhoods.
As you walk or bike across, the unobstructed views of landmarks like the Willis Tower and the river’s winding path provide a dramatic and awe-inspiring experience, especially during sunrise or sunset.
18.) 31st Street Beach
One of Chicago’s best features is city architecture and a beach. Play beach volleyball or lounge by the shore and get some of the city’s best views.
19.) London House Rooftop
It wouldn’t be a list of the best places to see the Chicago skyline without including London House. London House Rooftop Bar is certainly one of the most iconic rooftops in Chicago. They offer an ideal vantage point of seeing both the river and the city buildings.
20.) Cerise rooftop bar
The cerise rooftop bar has some incredible views of the city’s architecture. You can grab a drink, or in my case, sherbert ice cream, and take in the stunning views.
I hope you enjoy the beauty of the architecture and grand skyscrapers as much as I do. Let me know in the comments below some of your best places to see the Chicago skyline.
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