Me again

I've lived in all three cities, and I would rank them this way in terms of enjoyable places to spend time: 1) Toronto, 2) Chicago, 3) DC. However, upon first glance Toronto might seem to be the least interesting of the bunch - so let me explain why.

Toronto is one of the most cosmopolitan cities in the world. It's a great place to live. The food/entertainment/nightlife scenes are pretty happening. It's a great theater city, has wonderful parks. The people are friendly.

The problem is that it's kind of ugly, particularly in the downtown core where the city went through a huge building boom during the 60s/70s - just in time to hit the full brutalist stride. They also had the brilliant idea of building a massive highway along the lakefront - compare that to Chicago's park/beach system and sob.

Also the neighborhoods tend to be filled with lots of single-family or semi-detached red-brick buildings. Think working-class England but with more trees. It's not the most obviously gorgeous city in the world. It sort of has a generic, anywhere-North America kind of vibe - although in recent years there's been somewhat of a correction downtown, with some new blockbuster buildings going up and a bunch of the ugly monstrosities coming down (often turning into generic condo towers, but anyway...)

Toronto does have charms, however - it just takes a little bit of time to discover them. If you've only got a couple of days, you might find Montreal to be preferable - the city is gorgeous in all the right ways, it has a vibrant and unique (francophone/multicultural) culture, and it's far cheaper than Toronto in terms of accommodation.