My Favorite Big City Skylines (US & Canada)
Updated: Nov 6
Growing up in a small-town environment, I have always been extremely fascinated with cities large enough to have skylines. After all these years it was time to figure out my favorites by rating them. To do so I devised a simple three-category, 30-point rating system:
Variety of buildings (10 pts): when I look at the skyline, do all the buildings look brown, square, and the same height, or is an appealing mix of classic and modern lines?
Overall robustness of skyline in relation to city population (10 pts): Does a city of 350,000 people have 50 tall buildings or 2? Of course much of this has to do with regional development patterns, etc., but for now we're focusing on skyline aesthetics.
Wow factor/personal opinion (10 pts): Is there a building that impresses in its height or architectural significance? Is the city setting magnificent (think San Francisco) or mundane (Omaha)?
So as to better compare apples with apples, my first bunch of ratings focuses on the U.S. and Canada's largest cities (over 500k population). I rated 49 cities by looking up photos and 360 views on Google Maps. Without further adieu, here are my results:
HONORABLE MENTIONS: Charlotte, NC; Columbus, OH; Houston, TX (20/30)
10 (tie) Atlanta/San Francisco (21/30)
Based purely on architecture and variety of tall buildings, I'd have to give the nod to Atlanta, but then there's San Francisco's setting. And oh what a magnificent setting. Shimmering lights on the bay, the fog rolling in, the Golden Gate Bridge's constant presence. SF would rank much higher still were it not for its largely forgettable skyscrapers. Since 2017 its skyline has become much higher with the addition of an 802-foot residential tower and the 1,070 foot Salesforce Tower, 2nd tallest in California. The fact that these are built on earthquake-prone ground give it a slight edge in my book.
8 (tie) Dallas/Montréal (22/30)
Two very different cities, these. I give Dallas credit for living up to it's "Big D" nickname with a strong, modern, robust-looking skyline. On closer examination though, it's modern in an 70s/80s sort of way, as 20 of its 25 tallest buildings were built in those two decades!
Montréal, on the other hand, seems more blessed with quantity of skyscrapers rather than many standouts architecturally or height-wise. A closer look reveals a great deal of character, however; when this is combined with its beautiful location along the St. Lawrence, Mont-Royal towering behind, and the many classic church steeples, I have to give it a slight edge over Big D.
7) Boston (23/30)
Boston's skyline is unique in that its two tallest buildings (which have remained the same since 1976) are nowhere near the main cluster of downtown towers. As you can see from the photo above, it's difficult if not impossible to photograph the entire urban spread in one shot. What raises Beantown this high in the rankings is its beautiful harbor location, decent variety of old and modern, and two new 'scrapers joining the ranks of its top five in 2016 and 2019, respectively.
6) Calgary (24/30)
Calgary is a city on the rise, quite literally, as four of its five tallest have been constructed in the last decade. Many of its towers are modern and beautiful, but then there's also the spindly 1968 Calgary Tower and Saddledome in the foreground that remind one of the 1988 Winter Olympics. The Rockies aren't too terribly far away either, putting this western powerhouse a solid #6 in the rankings.
4 (tie) Toronto/Seattle (25/30)
Both of these northern cities are probably best known for their observation towers, the CN and Space Needle, respectively. The first time I realized that Seattle's iconic Space Needle is but 1/3 the height of the CN, I didn't want to believe it. In short, Toronto's skyline may be far more impressive, but it's also a significantly larger city. For Seattle's size it has a tremendous variety of buildings; when combined with its sound-side location and jaw-dropping backdrop of Mount Rainier, it punches above its weight and comes in fourth in my ranking.
3) Philadelphia (26/30)
The only thing Philly lacks is a dramatic mountain or ocean backdrop. Otherwise it's dang near the perfect skyline. Modern but with hints of classic lines (i.e. City Hall), super tall buildings that are densely packed for a very coherent feel. The several pyramidal towers make it instantly recognizable, and they're not resting on their laurels either, as several more giant monoliths have risen in the last decade. It may only be the US's 6th largest city these days, but its skyline punches above it's weight IMO... just like the famous fictitious southpaw who ran, grey-sweatsuited, through its mean streets.
1 (tie) New York/Chicago (28/30)
OK, I know it may not be satisfying to have a tie at the top of the chart, but after evaluation, these two broad-shouldered behemoths had a photo finish. How can any North American skyline defeat that of the Big Apple? It is beyond iconic, has quality, quantity, history, modernity, anything you'd ever want to see in a truly remarkable city.
Chicago, however, was the birthplace of the skyscraper. Its lakeside location is arguably even more beautiful, and it's also a fraction of New York's size population-wise. Taking a river/lake tour in 2018, I was able to appreciate these massive, iconic structures firsthand. If it wasn't for New York, Chicago would win any North American skyscraper contest hands down. Anyway, it's a tie. Love 'em both. Deal with it.
The Other End of the Table: the Most Forgettable Big City North American Skylines
Before I continue, I have to note that a poor skyline rating is no indication of how I feel about that city overall, or the people therein. We're simply talking aesthetics here.
9/30: Tucson, AZ; El Paso, TX
Welcome to the American Southwest, where beautiful skylines go to die. OK, that's a little harsh. In all seriousness though, cities that developed with limitless land availability often have the least impressive skylines. Tucson and El Paso are cities with well over 1/2 million residents; judging by their cityscapes, they look like maybe 200,000. Perhaps it's a moot point; when driving through the desert, any semblance of human activity can be a welcome oasis. (Side note: did you know that El Paso is closer to San Diego on the west coast than it is to Houston in its own state?! Look it up...)
7/30: Surrey, BC; Memphis, TN
Surrey is one of several on the "bad" list that aren't the primary city in their own metro area. Perhaps these gargantuan suburbs can be forgiven for their lack of a robust center. At least the few towers Surrey does have are modern and clean-looking.
Memphis, on the other hand, has no excuse. The largest city in Tennessee with 650,000 residents, it lacks an impressive skyline; the buildings it does have are largely yawn-inducing, and not particularly tall or memorable. The pyramid is certainly unique, but doesn't save it from a fate toward the bottom of the pile.
6/30: Washington DC/San Jose, CA
San Jose's skyline, while modern, is absolutely minuscule for it's population of over 1 million (3rd largest city in CA and 10th largest in the US!). Its tallest building is a whopping 286 feet, about the same as the tallest in... wait for it... Manchester, NH. Why is this? I have no idea. I'm sure San Jose is a wonderful place to live, with its Bay Area vibe and all, but it does not excel in the height department.
Perhaps Washington DC should come with an asterisk since it has extremely strict height regulations. While the Washington Monument and Capitol Building are impressive at first sight, a city of this size with no skyscrapers takes some getting used to. Is there anything inherently wrong with this type of arrangement? Perhaps not. But whatever the background of it, DC got one of the lowest ratings here, saved from the bottom of the heap only by its few iconic structures.
5/30: Albuquerque, NM; Brampton, ON; Fresno, CA
Now we're close to scraping the bottom of the skyline barrel. What's up with Albuquerque? A fast-growing city of 560,000 people with a total of one building taller than 300 feet, and only one of its top 10 having been built since 1990? I just don't get it.
Brampton, ON, with 600,000 people, similarly has very little in the way of high rise activity. Seems like a ginormous suburb. Thanks but no thanks.
Perhaps even more of a head scratcher is Fresno, which, with over a 1/2 million residents, has a tallest building whose roof wouldn't even be tallest in tiny New Hampshire. To top it off, the few slightly taller structures here are old and forgettable. Which brings us to our lowest-rated big city skyline....
3/30: Mesa, AZ
Believe it or not, this Phoenix suburb is the 35th largest city in the United States, larger than Miami, Cleveland, St. Louis, and many other more famous ones. Not only does this city not have an impressive skyline, it really doesn't have one at all. When searching for downtown among its suburban sprawl, I couldn't even find it on Google Maps. From what I can tell, this massive city's main area looks like a big strip mall (lined with beautiful palm trees, to its credit), but this is just about the most underwhelming city center I've ever seen. City dwellers from 100 years ago would be absolutely astounded that a half-million people would live in a place this sprawling.
So there you have it, my highest- and lowest-rated North American big city skylines. Which are your favorites?
Here's the full list if you're interested!