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20 Best Views of Chicago + 8 FREE Chicago Skyline Views

by valentina

The best views of Chicago are at rooftop bars, parking garages, and (yes) touristy observation decks. No matter what kind of experience you’re looking for, we’ll show you where to find the best Chicago skyline views. 

Chicago is one of the most iconic cities in America. It’s known for history, architecture, and ‘windy’ politicians as well as weather gusts. It’s the third most populous city in America, and there are over 115 skyscrapers! 

Across the world, Chicago ranks in the top 10 among cities with the highest number of tall buildings. You probably know all this, and that’s why you’re here. 😊 You’re looking for the most beautiful places in Chicago, and you’re in the right place.

woman looks out at Chicago skyline

Best Views of Chicago + 8 FREE Chicago Skyline Views

If you want to take beautiful pictures in Chicago, or simply have an impressive atmosphere, you’ll want to find a fabulous view of the skyline. We’ve put together a colossal list of the most scenic places in Chicago including the best rooftop bars, places you can visit for free, and touristy observation decks. 

view of Chicago's Art on the Mart

Best Views of Chicago

So, no matter if you’re looking for a daytime tourist activity or a romantic place to catch the Chicago skyline at night, this list will have something perfect for you. You’ll find out where to take the most impressive pictures of the Chicago skyline. These are also some of the best places to plan a romantic date in Chicago. 

view of Chicago from near Gibson's Italia

Rooftop Bars

Some of the best Chicago skyline pictures can be taken at rooftop bars. Rooftop bars offer an opportunity to dress up, enjoy a craft cocktail, and (best of all) soak in the unforgettable views. If you’re looking for an excellent accomodation, check out our list of Chicago hotels with epic rooftops.

If you enjoy taking pictures of city skylines at night, visit any of these rooftops bars. The best view in Chicago is here!

Little Wild

Little Wild (formerly Waydown Rooftop Bar) at the Ace Hotel offers a legendary Chicago view. Located in the lively Fulton Market neighborhood, the Little Wild is one of Chicago’s newest and most hip rooftops. 

Little Wild is an outdoor patio, so it is closed during wintertime. It features EDM and Hip Hop, often hosting live performances. 

view of Chicago from Waydown Nightclub

Book a room at the Ace Hotel.

Unlike other Chicago nightclubs, the Waydown is more low-key. You can’t book bottle service and you don’t need reservations. It’s meant to offer a relaxed vibe within the old-fashioned ‘watering hole’ style. 

The Waydown features a downtown Chicago view unlike any other! It’s a popular spot for Chicago rooftop photography since the Westside location offers panoramic views of the city skyline.


Located in the heart of Chicago’s Gold Coast, Devereaux is the Viceroy Hotel’s 18-floor rooftop bar and pool lounge. It’s also where you’ll find some of the most jaw-dropping rooftop views Chicago has to offer!

The Chicago scenery as seen from Devereaux is a very ‘in your face’ angle on the cityscape. Since you’re low to the group, but surrounded by tall buildings, you’ll feel very much a part of the skyline. 

3 women have drinks at Devereaux

Book a stay at the Viceroy Hotel in Chicago. 

The Chicago city view at Devereaux does not disappoint. Although, you’ll also enjoy the craft cocktails and fun atmosphere. Step outside the Viceroy Hotel, and you’ll be a few minutes walk from Chanel, Hermes, Dior, and many more designer favorites. 

Small plates served at Devereaux come straight from the kitchens of Somerset restaurant.

IO Godfrey’s

IO at the Godfrey Hotel is one of the best places to get rooftop access. Chicago’s River North neighborhood is where you’ll find it. IO at Godfrey’s is one of the larger rooftop venues in the city, and one of the best-known Chicago photo spots.  

Unlike many other rooftop bars, IO is open year-round. During the wintertime, the outdoor patio becomes an indoor venue. IO is well-known for exciting events and activities. They throw an epic Halloween party annually. You’ll find an event or brunch for practically any holiday on the calendar. 

view from IO Godfrey's Igloo on Halloween 2020

Stay at the Godfrey Hotel in Chicago.

Of course, you’ll also find fabulous views of the legendary Chicago skyline. Since you’re in River North on the 4th floor, you’ll have an up-close-and-personal view of the surrounding cityscape. 

Upstairs at the Gwen

The Gwen Hotel is located along the Magnificent Mile, it’s situated among the best shops in town. If you’re in the area, be sure to head to Upstairs at the Gwen for spectacular views and delicious cocktails.

Upstairs at the Gwen

Upstairs at the Gwen also offers wintertime curling on their spacious terrace. The Art Deco inspired vibes will put you at ease while you enjoy their captivating mixology.

Bar Avec

Formerly known as the Laurel Room, Bar Avec has one of the most unbeatable 360° views in the city! This seasonal rooftop terrace features a covered space and an open patio, so you can still go if it’s drizzling. 

woman drinks cocktail at Bar Avec

Bar Avec serves a small selection of Avec Restaurant favorites, as well as fabulous drinks. Avec is a great place to peruse an expertly crafted wine menu, or taste inventive cocktails

views from Bar Avec

If you’ve never eaten at Avec Restaurant… I must warn you, Bar Avec doesn’t quite do justice to the food. Come to Bar Avec for drinks and views, dine at Avec Restaurant for some of the most unforgettable food in the city!

Shanghai Terrace & Z Bar 

Shanghai Terrace and Z Bar are both located at the Peninsula Hotel on Chicago’s Magnificent Mile. The Peninsula Hotel is one of Chicago’s most esteemed 5-star hotels. It received a 5-star rating by Forbes Magazine since it first opened. It’s also been named #1 Hotel in Chicago, and #3 Hotel in the US by the U.S. News World Report.

seating at Shanghai Terracefood at Shanghai Terrace

Stay at the Peninsula Hotel.

Shanghai Terrace is a Chinese restaurant with phenomenal dim sum. It features Cantonese delicacies and steep prices. The vibe is 1930s supper club. The rooftop terrace is seasonal, but you can dine at Shanghai Terrace year round. 

view from Z Bar in Chicago

Z Bar is located a few floors above Shanghai Terrace, and the views are relatively similar. Both properties face East. The John Hancock building is featured prominently in the view.  Z Bar has an extensive cocktail menu, and offers some upscale bar food and small plates.

Nobu Rooftop 

The Nobu Hotel is located in Chicago’s West Loop. Nobu features a top-rated restaurant, and a panoramic rooftop terrace. The Nobu Rooftop is seasonal, and partially covered.

woman enjoys cocktail at Nobu Rooftop

Find ultimate luxury at Nobu. 

You can delight at views of the Sears Tower and surrounding cityscape. As Nobu is a Japanese inspired hotel, their restaurant and rooftop menu prominently features sushi. It’s regarded as one of the best places in Chicago to try sushi!


Cindy’s is a popular spot among tourists and locals. You’ll find this rooftop bar on almost any Chicago itinerary. Cindy’s isn’t known for skyline views (although you can see skyscrapers from here). Instead, it looks over Millenium Park. It’s one of the great places in Chicago where you can get an aerial view of the legendary ‘Bean’ or Cloudgate.

Cindy’s is a rooftop bar and restaurant. You can reserve a table here for brunch or dinner. It’s owned by the Chicago Athletic Association- a historic boutique hotel located right on Michigan Avenue in the Loop. Cindy’s is one of the best date night restaurants in Chicago. 

They serve New American cuisine made with locally sourced ingredients. They offer comfort food, biodynamic wines, as well as award-winning cocktails! This Chicago skyline restaurant does not disappoint!

Reserve a stay at the Chicago Athletic Association. 

The J. Parker

The J. Parker is another epic place to snap a picture of Chicago. Skyline views at the J. Parker face South from Chicago’s Northside neighborhood Lincoln Park. From the J. Parker’s all-season terrace, you can see the city skyline as well as unobstructed panoramas of Lake Michigan

The J. Parker sits on the top floor of the historic Lincoln Hotel. You can order small plates and hand-crafted cocktails. The J Parker doesn’t take reservations, entry is on a first-come, first-served basis. Visit no matter the weather, the J. Parker’s retractable glass atrium allows guests to stay warm and toasty year-round. 

Find out more about the Lincoln Hotel. 

London House

London House is another luxurious rooftop with excellent Chicago skyline views. The London House hotel is located in the Loop next to the Chicago River. You can visit for dinner, drinks, or come to one of their famous events.

woman at London House in Chicago, duskwoman at London House at sunset

Visit London House. 

If you visit London House, you’ll be sure to take some next-level pictures of Chicago. The outdoor patio at London House is best enjoyed at sunset. If you don’t have a reservation, you could try slipping the bouncer $20. We’re not the type to wait in long lines. 😉

NoMi Garden

NoMi is another stylish spot in Chicago’s Gold Coast neighborhood. Just across the street from the John Hancock Tower, and steps from Water Tower Place is where you’ll find NoMi. This restaurant and rooftop garden belong to Chicago’s Park Hyatt hotel.

NoMi is short for “North Michigan Avenue,’ one of the most glamorous parts of the Windy City. You can visit NoMi year-round, since the restaurant NoMi is indoors. Seasonally, you can also enjoy cocktails and small plates in the first-come, first-served, NoMi Garden. 

woman sips drink at NoMi Garden in Chicago

See photos of the Park Hyatt in Chicago.

You can snap Chicago city skyline pictures in either NoMi Restaurant or the Garden. Each venue offers a unique Chicago skyline view since the restaurant faces East and the garden faces Southwest. 

NoMi Restaurant features simple dishes made elegantly with only the freshest thoughtfully sourced ingredients. NoMi Garden is known for sushi and impressive seafood towers, all served on shareable plates. Don’t miss out on their global wine collection!

Terrace 16

Terrace 16 is named for the 16th floor of the Trump International Hotel in Chicago. It’s located on the Chicago River, and features some of the best Chicago skyline views!

Terrace 16 in Chicago

Stay at the Trump International Hotel in Chicago. 

Terrace 16 is open year-round. Their indoor section is quite small, but the seasonal outdoor patio is sprawling. If you are lucky enough to visit Terrace 16 during warmer weather, you’ll be able to snap some fabulous pictures of Chicago at night. This is one of the best places to get your Chicago skyline pics. 😃

ROOF on the Wit

The Wit Hotel is located in Chicago’s stylish South Loop neighborhood. ROOF at the Wit is a popular spot for young professionals and features weekly DJs and events. It’s also one of the best places to snap Chicago skyline photos.

The Wit Hotel is one of the top Chicago hotels with skyline views. This lounge is located 27 stories high, above it all! You can visit during the day, or even reserve a spot for brunch. Although, it’s much more popular for its nightlife. Travel+Leisure Magazine has called ROOF one of the top 3 Rooftop Bars in the world!

Book a room at the Wit Hotel. 

Free Chicago Skyline Views

You don’t have to get all dressed up or pay $20 for a cocktail to enjoy the Chicago city skyline. This next section will help you find the best places to take free Chicago skyline photos. 

view of woman in Chicago near Art on the Mart

Including parking garages, beaches, and hidden gems in the city. This is where you’ll be able to take phenomenal Chicago skyline pictures without breaking the bank

Lincoln Garage

The Lincoln Park Garage is a local gem and hidden attraction on Chicago’s northside. If you’re savvy enough to find it, you’ll be rewarded with unparalleled Chicago views.

Historically the parking lot for the Children’s Memorial Hospital which was torn down in recent years, the Lincoln Garage is still called the ‘Children’s Memorial Hospital Garage’ on Goggle Maps. It’s located on North Lincoln Avenue across from Velvet Taco and Philz Coffee in the Lincoln Common. 

view from Lincoln Garage in Chicago

You don’t have to park your car here to enjoy the views! Simply walk in, and take the elevator to the top floor of the garage and you’ll be awestruck by the panoramic view of Chicago. Skyline views like these are hard to come by. 

This is one of the lesser-known Chicago spots. Finding it is an adventure. If you love adventures like these, check out our list of unique experiences to have in Chicago. 

DuSable Bridge near Ghirardelli 

Tourists frequent the Magnificent Mile or North Michigan Avenue. It’s lined with the hottest designer shops like Tiffany’s, Tommy Bahama, and a massive three-story Banana Republic. 

view from DuSable Bridge in Chicago

If you walk down the Magnificent Mile south towards Ghirardelli (or the Apple store), you’ll be able to catch an awesome view of the skyline of Chicago. This is also one of the most popular Chicago skyline photo spots. So, don’t be surprised if you find a wedding photo shoot taking place or a swarm of tourists. To avoid the crowds, you may consider visiting early in the morning (sunrise), or a weekday during business hours. 

The Chicago River

The Chicago River is home to several of the best photography spots in Chicago. We’re talking about the section running East to West, parallel to West Wacker Drive (between Canal Street and Michigan Avenue). 

Some of the best Chicago photo spots along the Chicago River can be accessed for free, and others require that you book a tour. One of the most popular free locations is the Chicago Riverwalk which can be accessed near the DuSable Bridge or the William P. Fahey Bridge.

Woman wears flowy gown near Chicago's Loop facing the Chicago River

Another fabulous post can be accessed near Canal Street. If you map Gibson’s Italia and walk around the building, you’ll find the best place to take pictures of Chicago’s skyline at night (or sunset). You could also snap some photos near the Dearborn Bridge or the walkways east of Pizzeria Portofino.

kayaking on the Chicago River

You can also view the city skyline from inside the Chicago River! Book a Chicago skyline cruise or architectural tour. You can even rent kayaks and paddle along the Chicago River. The most popular Chicago skyline cruises depart from Navy Pier, but you can also find ones that are said through the Chicago River.

Navy Pier is one of Chicago’s favorite family destinations. It’s where you’ll find the Chicago Children’s museum, the beautiful Crystal Gardens, and the iconic Centennial Wheel. Best of all, the Chicago skyline view from Navy Pier is legendary. 

Navy Pier is a community stomping grounds. It hosts an assortment of free and paid events throughout the year including dance performances, art expos, and film screenings. Navy Pier is one of the most popular photography places in Chicago.

Navy Pier Garage View

There are awesome skyline views from all around Navy Pier. Although, there’s a secret spot that includes the Chicago skyline with Navy Pier’s famous Centennial Wheel. 

To get to this skyline viewing location, walk east (towards the lake) through the pier until you get to the parking structure. Take the elevators to the top floor. You’ll know it’s the right floor if you exit outside. It’s not a glamorous spot, but it’s free to visit and the view is to-die-for!

Around the Adler Planetarium

The Adler Planetarium skyline view is legendary. You can access it through the Lake Shore trail bicycle path, or drive and park nearby. The planetarium is one of Chicago’s premier museums. Stop by for a visit if you have time. Alternatively, make this a free visit by cruising around the surrounding area.

view from Adler Planetarium

 If you look at it on google maps, the area we’re talking about is aptly named the “Adler Planetarium Skyline Walk.” This is one of the best places to view the Chicago skyline from the south. The planetarium is situated east of all the other museums in Chicago’s famous Museum Campus Drive. Nearby, you’ll find the Shedd Aquarium, Field Museum, and Soldier Field. 

The Chicago skyline from Adler Planetarium’s surrounding lakeshore is incredible. You’ll see the entire city sprawled out before you. 

Bridge over South Pond

Chicago’s Lincoln Park neighborhood features the city’s free zoo and an expansive park with gardens, ponds, a lily pool, and a nature museum. There is a multitude of activities offered in this park year-round. It’s also one of the best places to take pictures of Chicago cityscapes. 

portrait of women taken at People's Gas Education Pavilion in Lincoln Park Chicago

In the summer, the zoo hosts beer festivals and food truck events. In the wintertime, you can view ZooLights. Whatever brings you to the Lincoln Park area, make sure to stop at the Bridge over South Pond for fantastic skyline views

Continue on the path towards the People’s Gas Education Pavilion – it’s an interesting art installation as well as one of the popular photography places in Chicago. Beautiful pictures of engagements, wedding parties, and families are taken here. 

BP Pedestrian Bridge

The BP Pedestrian Bridge is the lesser-known (formal) name for a very, very, popular tourist place in Chicago’s Loop. This futuristic bridge linking Millennium Park to Maggie Daley Park. It’s built from sheet metal and has won architectural awards for its innovative design. It claims to create a biomorphic allusion in a twisting form of a snake. 

woman walks on BP Pedestrian Bridge in long gown

The BP Pedestrian Bridge is one of the best Chicago photography spots! If you’re visiting Chicago, you need to take an afternoon to walk around this area. Millennium Park is where you’ll find the “Bean,” as well as the interesting Crown Fountain, Millennium Monument, and the Jay Pritzker Pavilion.

view from BP Pedestrian bridge, woman walks in pink gown

During the warmer months, there are seemingly endless free events to enjoy in Chicago’s Millennium Park. Maggie Daley Park boasts a famous Ice-Skating Ribbon as well as rock climbing. Take the BP Pedestrian Bridge between the two parks, and enjoy amazing views of the city of Chicago skyline! The further east you are on the bridge, the better the views.

North Avenue Beach

The best views of Chicago’s skyline from Lake Michigan are in between Oak Street Beach and North Avenue Beach. Catching the Chicago skyline from Lake Michigan creates a very in-your-face angle on the John Hancock. You can also see Navy Pier’s fireworks from here.

Start at Oak Street Beach and follow the trail to the Northeast most point from Oak Street Beach. This would be the southeasternmost point of North Avenue Beach. The spot is just south of the North Avenue Beach South Volleyball Courts. You’ll know when you’ve made it! There’s no more impressive view of Chicago. Skyline photography is a popular activity here. Chicago skyline from around North Avenue Beach lakeshore trail

The Chicago lakefront trails are quite lively in the summer, especially between Oak Street and North Avenue Beach. The trails are full of pedestrians, bikers, joggers, and skateboarders. These beaches are also great for sunbathing and playing volleyball in the summer months. North Avenue beach caters to a younger, wilder, crowd while Oak Street beach is more mature and relaxed.


Observatories offer some of the best views of Chicago for tourists and locals alike. While these are fabulous places to catch a city skyline view from above, they require an admission ticket. Skydeck and 360° Chicago are some of the popular Chicago beautiful places. 

360° Chicago

Some of the best Chicago pictures can be taken from the John Hancock tower. The most popular place in the John Hancock to take a Chicago skyline picture is 360° Chicago, an observation deck on the 94th floor. 

From the unique venue of 360° Chicago, you’ll be able to see the city from every direction. There’s also a thrill ride you can enjoy. Named, ‘Tilt’ the experience will allow you to reach out over the side of the building and peer down on Michigan Avenue from 1,000 feet above. 

3 women at the Signature Room at 95th

If you are looking for less tourist ways to visit the John Hancock tower, consider booking a table at the Signature Room for dinner or the Signature Lounge for drinks. 

The Signature Room is one of the most romantic places to view the Chicago skyline at sunset. Toast with a glass of champagne as you enjoy one of the celebrated Chicago photography spots.


Skydeck at Willis Tower (formerly known as the Sears Tower) offers some of the best views of Chicago skyline buildings up close. Once considered the tallest building in the world, the Willis Tower’s Skydeck observatory is 1,300 feet high in the sky!

Skydeck Chicago, two women

One of the exciting attractions at Skydeck is ‘the Ledge,’ a glass box that extends out from the building. There’s no better place to get downtown Chicago pictures than Skydeck’s ledge. These are unforgettable views of the city skyline. Chicago tourists are not disappointed! If you’re visiting this city for the first time, don’t miss out on the view of the Chicago skyline Willis Tower has to offer!

Best views of Chicago skyline pin

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Shane Prather February 5, 2019 - 9:12 pm

Love scoping out the best views around a new city! I haven’t been to Chicago since I was young but would love to return!

valentina February 6, 2019 - 1:46 pm

It’s a great summer destination! I’d stay away now, as we’re in a polar vortex 😉

krista February 7, 2019 - 6:07 pm

Chicago has such a beautiful skyline AND its for free! Last time I visited Chicago the wind chill legit stole my breath away I really need to go back!

blair villanueva February 8, 2019 - 9:58 am

Nowadays, many tourist attractions are starting to double their admission fee costs, which turn-off many tourists. Having a free access like this is a heaven sent! Gorgeous view!

Chris February 8, 2019 - 10:17 am

Great viewpoints, all of them. They would be amazing for shooting cityscapes at the right time of the day.

Daniel February 8, 2019 - 12:22 pm

What an awesome post and quite a way to take me down the memory lane! One of your photos is almost identical to a picture of me taken in Chicago, it’s crazy. Thanks for sharing this post, it brought back so many nice memories from the Windy city,

The little lai: Beyond limits February 9, 2019 - 2:44 am

Wow, I truly love how you were able to capture all the beautiful photos with your detailed post about this spot. I also love the fact that the Chicago’s Lincoln Park, which features the city’s beautiful free zoo and an expansive park with gardens, ponds, a lily pool and a nature museum has so much to offer that would definitely going to be an awesome experience. Thank you so much for sharing this with us.

Alexander Popkov February 9, 2019 - 10:51 pm

Never been to Chicago, but I know where to go now if I want to take some good shots. I would love to hang out there with my camera.


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