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Why so perplexed? Compare the tourist activity between the two cities. Even on a cold winter night you will find hundreds of tourists on Michigan Ave or the museum campus in Chicago. Where in Toronto do you see hordes of tourists?
Nope you won't see hordes of tourists. You will actually see hordes of normal residents going about their daily lives on a normal day. Not sure why you would bring up "tourist activity" as the underlying assumption for street activity in any given city. Tourists make up a tiny proportion of the population and pedestrian activity in large cities like Toronto and Chicago.
Why so perplexed? Compare the tourist activity between the two cities. Even on a cold winter night you will find hundreds of tourists on Michigan Ave or the museum campus in Chicago. Where in Toronto do you see hordes of tourists?
I don't know about "hordes" but there are plenty of tourists and tour groups to be seen around Yonge-Dundas Square, the Distillery District, the CN Tower/Entertainment District, and around the Royal Ontario Museum.
I'd say that Toronto's older, pre-war areas more resemble various parts of NYC's outer boroughs than they do Chicago's nabes, so I voted for Queens.
I picked Queens because it is the borough that resembles Toronto most. The Bronx is dominated by high rise projects. Brooklyn is more low rise apartment dominated and while highly diverse, it's more characterized by areas dominated by a specific group. Queens has a mix of high rises and SFHs, a fairly similar ethnic mix and was built up around the same time as much of Toronto.
I don't know about "hordes" but there are plenty of tourists and tour groups to be seen around Yonge-Dundas Square, the Distillery District, the CN Tower/Entertainment District, and around the Royal Ontario Museum.
I agree and although Chicago gets more overall visitors - its the main city of the U.S midwest an area more populous than all of Canada so it stands to reason they'd get more visitors.. With that said and this is going to upset Sandman - Toronto gets more International visitors from overseas (not including the U.S) than Chicago does total International visitors including Canadians.. Toronto's attractions are more spread out than Chicago's but I personally see HORDES of tourists at the CN Tower and Ripley's aquarium. I suggest Sandman go there next time he is in Toronto - he'll get his wish, or apparently his nightmare..
With that said - neither are big 'tourist' cities and that isn't a bad thing either as Bostonkid rightly put it.
You always get your back up when Toronto's skyline comes into the picture.. Nobody said (and it wasn't my intent to state) that Toronto has a more impressive one, just that it is a pretty big darn DT core. We all know that Chicago has better scraper architecture.. With that said, T.O's skyline and core is growing gangbusters so one of these days someone is going to bust out the figures for number of highrises and height of those in each core and what is everybody in Chicago or its boosters going to do when T.O comes out on top - its going to be a nightmare for them.. Don't worry Sandman - it'll take T.O time to reach the height of Chicago - as for density well I don't really think they are far off in terms of core highrise density already. Everybody will or should agree Chicago will always have the better scraper architecture - its growth took place at a time when where we all look back with nostalgia - its classic but they simply don't build em like that anymore. As far as Chicago having ownership of more highrises and a bigger core than Toronto - I think people need to seriously look at what is going on in Toronto and just accept what is probable and that is if T.O continues to boom/grow in its core area the way it has been and Chicago's core growth continues to be muted in comparison - T.O will have the bigger/denser and maybe even taller core... Its no big deal..
These are just skylines too - there are far more important things about a vibrant city than that and other posters in here have eluded to it.
I was in Toronto in July of last year and in Chicago in May of the year before. My impression -- Downtown Toronto is at least as (if not more) vibrant as Downtown Chicago. The King Street/Queen Street corridor was hopping late into the night for at least 10 blocks -- busier than any nightlife area in Downtown Chicago. (I know that some of Chicago's most active nightlife areas are away from downtown but still). Young people everywhere. The streetcars add a special charm and European vibe that's very enjoyable.
I still think that Downtown Chicago is more impressive and there is no equivalent to the Magnificent Mile in Toronto (Bloor St is a poor analog), but for overall activity level in and around downtown I would have to give the edge to Toronto based on my last visit to each city (which, admittedly, is limited perspective).
The one caveat is that it was spectacular weather on my visit to Toronto, but unseasonably cold in Chicago (in the 50s). That said, any city that empties out when it gets a little chilly makes me a bit suspicious.
An honest post - it'll drive people crazy that an American would say that.. College street further west of the core is also hopping at night along with Bloor West in the Annex..
and how is it a compliment to compare toronto with chicago? It almost sounds somewhat condescending, like "you are lucky to be compared to us but nice try". I mean, the two cities have almost nothing alike except location and maybe skyline. Toronto has much more similarity with the likes of sydney or melbourne, especially in culture and urban planning.
Chicago has been called the "Most American City" and I tend to agree. It has a better developed Lakefront from its world class Parks to beaches and Harbors.
Unlike some other cities, Chicago preserved its lakefront from industry and for public use. As for downtown, it has evolved through many eras and the decay aspects in the 60s 70s. Even Times Square and parts of Manhattan did in that era. Luckily it was able to have most of its oldest history in buildings preserved and built great examples of newer architecture.
I think comparisons with Toronto comes not from Architecture? But a long stretch of high-rise living along its waterfront as Toronto has evolved.
Chicago downtown and lakefront
What is a world class park on a lakefront? Is it because it has nicely manicured parks on its lakefront that somehow the parks are world class.. Am I the only person who thinks a world class lakefront and parks in or close to it is a big snore... Its nice don't get me wrong but the whole world class thing is kind of silly. Chicago is a world class city and so is Toronto each for similar and different reasons. They're doing things with T.O waterfront btw to improve it.
Thanks! Come up in the summer... best time to visit
I'll go in the winter, need to escape the cold.
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really wanna make it down there some time this year.... 
