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Chicago vs. Toronto: Which city has the best skyline?

Before visiting Chicago for the first time, everybody told me that I was going to love the city. They would tell me that it’s similar to Toronto, except that it has better architecture and a better waterfront. Having now visited the city, I not surprisingly have a lot to say on this matter. But I need another day or so to formulate my thoughts.

In the interim, I thought it would be fun to host a little competition. Given that both Chicago and Toronto are Great Lake cities of comparable size (and formally sister cities), I’d like to know: Which city, do you think, has the better skyline? Please respond in the comment section below and make sure to include your location (so we all know if you might have a hometown bias).

To help you make your assessment, here are a few photos. Below is one that I took of the Chicago skyline from the architecture boat cruise we went on yesterday afternoon. The building directly in the center is the Trump Chicago.


And here’s a photo of the Toronto skyline that I took from a water taxi earlier this summer.


But since these photos only represent one particular vantage point (me on a boat), here’s a set panoramic photos that I found online (Chicago & Toronto). I want to be as fair as possible.



I think this one could go either way. But I personally like the variety that the lit up CN Tower and Sky Dome (Rogers Centre) bring to Toronto’s skyline. Overall, it feels a lot more modern and exciting to me. So I pick Toronto. What about you?


  1. Artemis

    I’ve been to both cities. Toronto, IMO, has the third best skyline in North America. The top two have to go to New York and Chicago. While Toronto has more high rises than Chicago, Chicago has more skyscrapers than Toronto. Generally speaking, a skyscraper is any occupiable building exceeding 150 meters tall (about 492 feet). By that definition, Toronto has about 30+ skyscrapers (and growing), while Chicago has over 100. When it comes to big buildings, Chicago blows Toronto away. This is why Chicago’s skyline is one of the world’s greatest and most iconic skylines. It’s incredibly massive, rich in a variety of architectural styles, and stunning in the way it hugs the coast line along Lake Michigan. Toronto has a great skyline, no doubt, but Chicago is just breathtaking.


  2. John Ranno

    Chicago has architecture and a waterfront that Toronto can’t even rival, so overall it’s better. However to be fair, Toronto is a reasonably clean city, but it’s along a more polluted lake.


    • Keisha

      I like Toronto skyline better.
      I’ve never been to Canada. I live in Midwestern United States.


  3. Darren

    They are both magnificent cities. Toronto is cleaner with less crime with a cool island airport that superimposes airplanes against it as a backdrop.

    Chicago is all things Jazz with great steak houses and a cool post-gangster vibe.

    Chicago feels like Toronto and Toronto feels like Chicago. They are only a one-hour flight from each other and both are to be tremendously applauded. With a few more centuries of growth, they will butt up to each other creating the largest city in North America. Take that NYC.


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