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?

Over the long weekend I wrote a post called “On medium density development.” My argument was that Toronto has gotten exceptional at building infill towers, but not so great at midrise and other medium density infill solutions. Though to be fair, we are starting to see more and more of that today.

Well it turns out that Chicago is in a similar, if not worse, position. According to Aaron Renn of the Urbanophile blog, most of the city (outside of the city center) only allows for single family homes. Though in some cases you may be allowed a duplex or triplex.

Here’s a map:

The red is where you’re only allowed to build single family homes. The yellow represents non-residential uses (parks, industry and so on). And the remaining black is where you’d see high density development. Note how it runs all along Lake Michigan. Both Toronto and Chicago are developing in a similar “T” formation.

Now, some of you may be saying to yourself: So what? But it’s important to remember that this type of zoning effectively creates a supply constraint in the market, which, as I’ve argued before, will drive up prices. Chicago may as well be surrounded by mountains, because that red area seems almost untouchable from a development standpoint.

With so many people rushing back to cities today, a lot of them are struggling to create the same market environment that our parents enjoyed. You know the one where you finish school, get a job, and then you’re able to buy a house. But I think it’s because many of our cities are at a turning point, and yet are clinging to outdated principles of city building, such as single-use zoning.

But I’m certainly no expert on Chicago, so if you are, please speak up in the comment section below.