6 Places to View Great Skylines
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Every city has its’ own unique top spots for urban photography. In my guide, I will cover several fantastic (and easily accessible) sites for viewing the great skylines of: Chicago, Pittsburgh, Dallas, Cleveland, L.A., Boston, and New York.
In my opinion, Chicago & Pittsburgh are easily amongst the most scenic skylines in the country, if not the world. In addition, the beautiful greenery surrounding Boston gives us numerous options for uniquely attractive views. Gorgeous Lake Erie surrounds Cleveland and the mesmerizing Santa Monica mountains perfectly frame L.A. And, Dallas frequently rates as one of the reader chosen favorites. Of course, we can’t forget about NYC and the iconic Empire State building observatory.
The great thing is that many of these cityscapes can be viewed for free. There is almost always an alternative way to enjoy the same great view at a fraction of the cost. If I have personally found a great free view, I have noted it. Also, I will be adding new fantastic viewing destinations as I come across them, so check back occasionally.
Chicago
Chicago is hands down the number 1 skyline in the country and I am not just saying this as a native. The gorgeous architecture with Lake Michigan in the background is just so photo worthy. Every native knows the secret: the Adler Planetarium is the best place to take pictures of the famous cityscape. The views are absolutely spectacular and you will pay nothing.
If your visit falls during the nice season, I recommend a gorgeous bike ride on the 17 mile Lakefront Path. By hopping on this ride, you gain easy access to most of the city’s top landmarks and museums in the same day! Keeping true to its’ nickname, “the Windy City,” a windy day can dampen an otherwise pleasant ride.

Where to go for the best views: The Planetarium is located at: 1300 S. Lakeshore Drive. I usually start the bike path around Millennium Park (there are various parking garages in the area).
Update: For those who don’t mind spending a few bucks, I highly recommend a visit to the Willis Tower Skydeck. This iconic attraction is one of the few worthy of the high admission cost in my opinion.
From the 103rd story observatory, you will stand on a piece of 1.5 inch glass as you take in marvelous views of the top city. A bit scary as you can see everything beneath you in clear detail, but really an exhilarating experience where you can take all sorts of creative photos.


Pittsburgh
Pittsburgh was one of my favorite cities I’ve lived in thus far. It’s so interesting and underrated with fabulous museums, a great local dining scene, and so many wonderful parks. I really love the city (check out my guide to the best of the ‘Burgh) and all the interesting bridges. The absolute best view of the incredible skyline can be viewed after a ride on the historic Duquesne Incline. An antique cable car ride will take you 400 feet up to this observation deck.
Here you will enjoy once-in-a-lifetime panoramic views of “‘The Steel City,” the three rivers (Ohio, Allegheny, and the Monongahela), and its’ many fabulous bridges (the city is nicknamed “The City of Bridges”). The view is so amazing that USA Today voted it one of the Top 10 Places Worldwide for City Views. I totally agree – what a view! And, the view is equally striking both day and night.


Where to go for the best views: The incline is located at: 1197 West Carson St. Note: if you would rather not pay the $5 per person fee for the ride, you can opt to drive up Mt. Washington and enjoy the view for free. Of course, I recommend the full experience if you don’t mind shelling out a few bucks.
Dallas
Dallas is no doubt home to the most stunning skyline in Texas, and definitely ranks as the best of the Southwest. In 2014, readers of USA Today voted Dallas the best International skyline. The best way to take in the beauty of “The Big D” is via the observation deck at Reunion Tower.
From 470 feet in the air, the panoramic views of the grandest city in Texas are unparalleled. It’s no Empire State building, but a great experience for Texas. It’s a great activity for first time visitors who want to learn more about the city.

Where to go for the views: Reunion tower is located at: 300 Reunion Blvd E.
Cleveland
Although Cleveland’s small skyline will not be winning awards anytime soon, the serene setting on beautiful Lake Erie definitely earns it some bonus points. Add in an easily accessible location in one of the country’s most beautiful urban parks, and this one is a definite bucket list contender. Edgewater is a gorgeous greenspace home to a lengthy paved biking path, 9000 feet of shoreline, public and dog beaches, picnicking areas, and so much more. I love walking along the lake here during the summer season.
It’s one of my favorite places in the city to enjoy the scenery, take a bike ride, and pincic. I love collecting seaglass here (as well as most other Lake Erie beaches). Don’t forget to take your pic next to the famous Cleveland script sign (there are 6 throughout the city).

Where to go for the best views: Edgewater Beach is located at: E. 55th Street.
Los Angeles

L.A. may be more known for its’ negative attributes like traffic, smog, and congestion. However, there are many beautiful beaches, parks, and public attractions for everyone to enjoy. During my time living here, I spent more time in nature than visiting the Hollywood attractions that all the tourists love. To me, the best part of living in this city is access to wonderful museums and recreational areas.
One of these is beautiful Griffith Observatory, a combo hiking area/scenic overlook/astronomy tower. Thanks to a generous donation from philanthropist, Griffith J. Griffith (whom the observatory is named after), this city landmark will always be free to the public. This is also where you will find the best overlook of the Hollywood sign.
There is also an incredible hike that takes you really close to the iconic Hollywood sign. I really love this hike – not only do you get to take funny photos with the sign in the background, but I love gazing at the city and surrounding mountains and mansions. Best of all is the fabulous overlook of L.A. (on a clear, non smoggy day that is!).
Where to go for the best views: The Griffith is located at: 2800 E Observatory Rd. in Los Angeles.
Boston
Although Boston is not home to one of the best skylines in the country imo, there are some great natural areas where you can hike and take in city views. In my opinion, it does win the award for best urban recreation near a big city. Let’s just say that I never ran out of hiking options during my 2+ years living here. My favorite place to view the city scape is the highest point in Blue Hills Reservation, Great Blue Hill.
After a short, steep hike, you can enjoy panoramic city views via Elliott Tower. This location provides a unique view of the city from afar; the beautiful forested hills only add to the enchantment. Note: the Bunker Hill Monument (located along The Freedom Trail) is another fantastic place to take in the cityscape. You will have to climb 294 steps, but it’s worth it. You can’t go wrong with either option.


Where to go for the best views: The Red Trail hike at Blue Hills begins at 695 Hillside St. in Milton. Bunker Hill is located on the Freedom Trail (you can start near Boston Common). Both the reservation and trail are free.
New York

The top views of “The Big Apple” can be enjoyed via the classic Empire State building observatory. You can take in the views day or night (or both), from the 86th and/or 102nd floor observatories. It took me several visits to the city before I finally caved in and paid the hefty fee, but I am glad I did because it is a once-in-a-lifetime experience.
You will get to ride in a glass elevator which is pretty cool. At the top, you can look out and see so many famous landmarks including the Statue of Liberty and Central Park. An A+ all the way in my book. Prepare for crowds – we lucked out and basically had the entire place to ourselves on a really rare slow day! Bonus – you can walk over to NY Pizza Suprema for the best pie in the city after your visit.


Where to go for the best views: The Empire State building located at: 20 W. 34th Street. On a side note, there are many places to view the NYC cityscape for free including Brooklyn Bridge Park.