Canadian Skyline Thread III

[koops65]

It was named Waterloo in 1816, just after the battle of Waterloo, in Belgium. Back then there was no idea that Kitchener (Berlin) would grow the most.

[Wigs]

Originally Posted by MolsonExport

why is the region named "Waterloo" when Kitchener has long been larger, and judging by those figures, Cambridge too?

When did Kitchener meet its Waterloo?

Why is London geographically part of Middlesex County, but politically separate YET Middlesex County has its HQ/County administration building in London?


C'mon Southwestern Ontario folks, make it make sense

[shappy]

It would be cool to see KWC become a large city. Kitchener has decent bones and has a lot of developable land. The CBD would be located there. Waterloo would be this ugly but dense hub next to Kitchener. Meanwhile Cambridge is this picturesque town - looks like it belongs along the river Thames. It would be the cultural heart of the city... think we got something here!

[Nouvellecosse]

Would be nice to see major cities a bit more spread out across the country though. Or leat least across the province

[hipster duck]

Originally Posted by shappy

It would be cool to see KWC become a large city. Kitchener has decent bones and has a lot of developable land.

Interestingly, I have the exact opposite view as you.

KWC is a big city - it has probably the most diversified economy of any metro other than the biggest 6 in the country, and it has big city things like rail transit, and an urban freeway system.

Kitchener has mediocre bones. I would say that's the region's Achilles heel, actually. KW was not very big before the war, and the pre-war neighbourhoods are either very affluent (because Kitchener has tech money) or very small town slummy, with little in between. It's definitely not a Saint John, NB type place with beautiful architecture waiting to be gentrified.

And Kitchener has almost no developable land left. I think that the region depends on groundwater and it has to preserve land to maintain its aquifer.

[jonny24]

Originally Posted by koops65

It was named Waterloo in 1816, just after the battle of Waterloo, in Belgium. Back then there was no idea that Kitchener (Berlin) would grow the most.

More specifically, it was the name of the county, (and township, confusingly), not just the town. So that carried over the "region".

[someone123]

Originally Posted by hipster duck

Kitchener has mediocre bones. I would say that's the region's Achilles heel, actually. KW was not very big before the war, and the pre-war neighbourhoods are either very affluent (because Kitchener has tech money) or very small town slummy, with little in between. It's definitely not a Saint John, NB type place with beautiful architecture waiting to be gentrified.

Kitchener (just the city, not the region) is actually a bit similar in physical layout to Moncton, or at least was before the recent boom. I am less familiar with it these days.

Saint John literally has a bunch of old lots in historic urban areas with no houses on them and the like. And it's sort of a touchy subject but it has a lot of urban poverty with uses in some grand old buildings that may or may not support them in the long run. I suspect would be better if it gentrified more and some tenants moved into better quality modern towers rather than living in crumbling Victorians. I think this would have naturally happened had the region become more populated. But it's hard to support 50,000 people worth of Victorian houses in a city with 130,000.

[Coldrsx]

https://media.licdn.com/dms/image/v2/D56...vUyDNOI36uWjqXWs9wpENINbraoV_0bOxwPpHrnE


https://t.co/DXX1LOgoqI

[Segun]

Originally Posted by MonkeyRonin

Montreal definitely won't feel bigger than Chicago - after all, it is quite a bit smaller, and doesn't have the same historic grandeur - but IMO at least it absolutely is more urban. It's denser, older, more multi-family oriented, the built form is finer-grained (narrower streets, smaller blocks, etc), it's more pedestrian/transit/bike-oriented, and just has more street-level vibrancy in general (partly cultural, and partly a function of the reasons above). Montreal just feels like a tighter, more active & lived-in city than Chicago; with its sort of grand, airy, spacious quality.

i disagree Chicago compared to Montreal, especially with it being more urban. Hold on now!

Density and infrastructure: The only areas that stand out to me as being denser in terms of having that fine grain feel is the area of Old Montreal stretching through Latin Quarter, Chinatown and Le Plateau.

While Chicago doesn't have much of an "old fine grain" area, Montreal doesnt have much of a "concrete jungle" like area full of wall to wall pre-war highrises and pre-war 6-12 story buildings like Chicago's Uptown, or the South Shore on the South Side.

The rest of Montreal is nearly identical to Chicago, with walled in, tree-lined streets of 2 flats, 3 flats and 3.5 to 4 story apartment buildings.

I agree that Montreal does the promenade/public space aspect better, hell it might be the best city in North America for it, yes even above New York!

Vibrancy:

i dont get how anyone could say that Chicago is less vibrant, thats just flat out wrong IMO. I doubt downtown Montreal has enough space to hold the combined crowds of the area stretching from the Loop to the end of the Mag Mile. Im trying to figure out the rationale for this assertion. Maybe its because MTL does a better job of connecting its low-rise neighborhoods to downtown? In Chicago, theres zones where it drops off then starts again, whereas say, Le Plateau flows right into downtown. Never the less, I could put a neighborhood like Lakeview right next to Le Plateau and couldnt notice the difference, other than the types of stores. Its just that Lakeview doesnt flow into downtown, its miles away.

Outside super-busy ares such as Le Plateau, Montreal reaches and maintains a respectful threshold of "vibrant" or "busy", but not crowded, (at least not crowded enough to make a standout impression on me).

This is where Chicago exceeds Montreal. I can visit MTL and see all the areas of "vibrant" or "busy" pedestrian activity within a few days, to the point where I've almost memorized them. They're conveniently located in a contigous area, and dont veer far from Metro stations, whilst Chicago has miles upon miles upon miles of vibrant pedestrian oriented neighborhood districts that aren't anywhere near the EL and often disconnected from a contigous experience. Its rare that visitors and tourists ever step foot in these areas. (Devon Street, Little Village, Belmont/Central, Clark Street in Rogers Park, Andersonville, 18th Street in Pilsen, Lawrence Ave in Albany Park, 79th Street on the South Side, etc) Chicago has endless streets after streets that flow into the horizon with "busy" foot traffic (Milwaukee, Clark, Belmont, Halsted, Lawrence, Lincoln to name a few) whereas Mont Royal, Sherbrooke, and St Laurent are the only ones I can think of for Montreal. At one point in Montreal the commercial activity just stops, and the major commercial streets turn into low rise residential avenues. Chicago keeps the vibrancy up to where theres a major walkable commercial street every half-mile (with the exception of the bungalow belt and slums). Toronto doesnt have this dynamic either.

i think people are underestimating how big and urban Chicago is or overstating how vibrant Montreal is. Maybe its because Chicago has more of an ebb and flow, while Montreal is more consistent. We all have our biases, but also our experience frames our perception. As a lifelong Chicagoan, Montreal doesnt strike a chord with me as being more urban. Theres nothing that makes me go "wow, this is so different than Chicago!", other than Old Montreal. NYC is the only city in the US and Canada that I can comfortably use that superlative. Montreal is similarly urban, but smaller in its spread.

[shappy]

Originally Posted by hipster duck

Interestingly, I have the exact opposite view as you.

KWC is a big city - it has probably the most diversified economy of any metro other than the biggest 6 in the country, and it has big city things like rail transit, and an urban freeway system.

Kitchener has mediocre bones. I would say that's the region's Achilles heel, actually. KW was not very big before the war, and the pre-war neighbourhoods are either very affluent (because Kitchener has tech money) or very small town slummy, with little in between. It's definitely not a Saint John, NB type place with beautiful architecture waiting to be gentrified.

In 1941 the region had a population of about 62,000 and, in the same year, Calgary had about 89,000 which is not a very significant difference. I don't think prewar size and prominence would have as much future impact as suggested. It does play a role, but with solid urban design going forward, it can still work. I was just musing btw, but given how it's quickly growing, it is interesting to think about. Imagine Cambridge with a bunch of nice modern infill around the old central parts along the river with a tall CBD in the distance... would be pretty cool.

Originally Posted by Nouvellecosse

Would be nice to see major cities a bit more spread out across the country though. Or leat least across the province

Sure, but realistically it's more likely to happen in Southern Ontario than most other parts of the country. And it's not unprecedented. Washington and Baltimore, Philly and Wilmington are both closer.

[Wigs]

Segun, when's the last time you visited Montreal?

From 2004-2024 the City of/Ville de Montréal grew by ~307,000 and the Metro/Montréal CMA grew by almost 900,000. A substantial amount of that growth has occurred in less than a decade.

To me the best features of Montreal are the activation of public spaces, parks/parklets and pedestrianization of streets. Combined with a great subway system and walkable, human scaled streets and it's overall one of the best cities in North America.
*edit* it's also one of the most bike friendly cities in North America

Is it better than Chicago? Forget apples to oranges, that's like comparing a Chicago dog to poutine and an Italian beef to Montreal bagels

[Segun]

^ It's been a while. Maybe 2012 or so. Maybe there's been so much more built since then, who knows. Is it enough for me to say that's its more urban though? Chicago has grown also, unfortunately it's harder to track because of the dual nature of Chicago, more people left the decaying areas while more development occurred in the already busy areas. "Better" is extremely subjective. I don't find New York better, despite it's massive size difference from the next city. I could write an essay about what I dislike about NYC's built form.

I agree that the pedestrianization of street life is Montreal's strongest suit. It's what stood out the most in my first visit, not how "much more urban and vibrant" it was. It's crazy because I find it to the most similar city to Chicago in the US and Canada. Like I said, New York is the only city in the US and Canada to have that distinction of being more urban, in both intensity and spread.

[shappy]

^ I'm curious how you'd compare Chicago and Toronto. I haven't been yet but I think it'll be my next US city I visit.

Also just want to mention that I always thought that Chicago (through pictures alone, however) resembles Montreal's neighbourhoods more than Brooklyn, Philly or Boston. And a lot of people like to compare Montreal to those places.

[softee]

Toronto is much more vibrant in terms of pedestrian activity both downtown & in the old, pre-war urban neighbourhoods than Chicago. Only NYC is busier among cities in the U.S. & Canada. Of course this won't go over well among some of the forumers on here, but it's just reality now. It doesn't mean Chicago isn't a great urban city, it's just that Toronto has levelled up & passed it.

[MonkeyRonin]

Originally Posted by Segun

i disagree Chicago compared to Montreal, especially with it being more urban. Hold on now!

Density and infrastructure: The only areas that stand out to me as being denser in terms of having that fine grain feel is the area of Old Montreal stretching through Latin Quarter, Chinatown and Le Plateau.

While Chicago doesn't have much of an "old fine grain" area, Montreal doesnt have much of a "concrete jungle" like area full of wall to wall pre-war highrises and pre-war 6-12 story buildings like Chicago's Uptown, or the South Shore on the South Side.

The rest of Montreal is nearly identical to Chicago, with walled in, tree-lined streets of 2 flats, 3 flats and 3.5 to 4 story apartment buildings.

I agree that Montreal does the promenade/public space aspect better, hell it might be the best city in North America for it, yes even above New York!

Vibrancy:

i dont get how anyone could say that Chicago is less vibrant, thats just flat out wrong IMO. I doubt downtown Montreal has enough space to hold the combined crowds of the area stretching from the Loop to the end of the Mag Mile. Im trying to figure out the rationale for this assertion. Maybe its because MTL does a better job of connecting its low-rise neighborhoods to downtown? In Chicago, theres zones where it drops off then starts again, whereas say, Le Plateau flows right into downtown. Never the less, I could put a neighborhood like Lakeview right next to Le Plateau and couldnt notice the difference, other than the types of stores. Its just that Lakeview doesnt flow into downtown, its miles away.

Outside super-busy ares such as Le Plateau, Montreal reaches and maintains a respectful threshold of "vibrant" or "busy", but not crowded, (at least not crowded enough to make a standout impression on me).

This is where Chicago exceeds Montreal. I can visit MTL and see all the areas of "vibrant" or "busy" pedestrian activity within a few days, to the point where I've almost memorized them. They're conveniently located in a contigous area, and dont veer far from Metro stations, whilst Chicago has miles upon miles upon miles of vibrant pedestrian oriented neighborhood districts that aren't anywhere near the EL and often disconnected from a contigous experience. Its rare that visitors and tourists ever step foot in these areas. (Devon Street, Little Village, Belmont/Central, Clark Street in Rogers Park, Andersonville, 18th Street in Pilsen, Lawrence Ave in Albany Park, 79th Street on the South Side, etc) Chicago has endless streets after streets that flow into the horizon with "busy" foot traffic (Milwaukee, Clark, Belmont, Halsted, Lawrence, Lincoln to name a few) whereas Mont Royal, Sherbrooke, and St Laurent are the only ones I can think of for Montreal. At one point in Montreal the commercial activity just stops, and the major commercial streets turn into low rise residential avenues. Chicago keeps the vibrancy up to where theres a major walkable commercial street every half-mile (with the exception of the bungalow belt and slums). Toronto doesnt have this dynamic either.

i think people are underestimating how big and urban Chicago is or overstating how vibrant Montreal is. Maybe its because Chicago has more of an ebb and flow, while Montreal is more consistent. We all have our biases, but also our experience frames our perception. As a lifelong Chicagoan, Montreal doesnt strike a chord with me as being more urban. Theres nothing that makes me go "wow, this is so different than Chicago!", other than Old Montreal. NYC is the only city in the US and Canada that I can comfortably use that superlative. Montreal is similarly urban, but smaller in its spread.

It's been a while seen we've seen you around here! Always appreciate a post from an insider's perspective; and to your point we've all got our own biases (which naturally favour the Canadian cities in this forum). To some extent, arguing whether Chicago or Montreal or Toronto is more vibrant or urban is an act in splitting hairs - in the North American urban hierarchy New York is clearly in its own tier, while Chicago, San Francisco, Toronto, and Montreal are probably in a fairly evenly-matched second tier. I'd put Boston, Philly, DC, and Vancouver a tier below; then followed by the rest.

One of my favourite things about Chicago though is the massive scale and extent of its interesting, urban, pre-war neighbourhoods - from Evanston in the north to the South Shore, and out west to Forest Park. There are a ton of vibrant neighbourhoods with their own character - by sheer quantity, Chicago has any other non-NY city beat by a long shot. But, at the same time, the thing about all of these neighbourhoods is that they're somewhat disparate and disconnected; often separated by gaps in the urban fabric - whether that be freeways, abandonment, or industrial areas. There's simply a difference in experience of being able to walk for hours throughout continuously vibrant neighbourhoods versus ones where things sort of stop and start.

The other thing about all of Chicago's commercial strips is that there are simply too many of them relative to the population they support, so you get these sort of low intensity strips with a mix of businesses, residential buildings, and vacant storefronts. In Montreal and Toronto's case, there are fewer of these, so the ones that do exist are fuller and busier. Basically, Chicago is overbuilt; while Toronto and Montreal are underbuilt relative to their current populations. IMO, Chicago really needs a million or so more people for the human activity to match its built environment; whereas its Canadian counterparts have a sort of teeming quality today because they simply were never planned or built to house as many people as now reside in them.

The other area where Chicago really shines though, is in the Loop, which is easily the most impressive downtown core outside of Manhattan. Toronto isn't quite at the same level, while Montreal's downtown is still a long ways off.

[logan5]

Originally Posted by Segun

Vibrancy:

i dont get how anyone could say that Chicago is less vibrant, thats just flat out wrong IMO. I doubt downtown Montreal has enough space to hold the combined crowds of the area stretching from the Loop to the end of the Mag Mile. Im trying to figure out the rationale for this assertion. Maybe its because MTL does a better job of connecting its low-rise neighborhoods to downtown? In Chicago, theres zones where it drops off then starts again, whereas say, Le Plateau flows right into downtown. Never the less, I could put a neighborhood like Lakeview right next to Le Plateau and couldnt notice the difference, other than the types of stores. Its just that Lakeview doesnt flow into downtown, its miles away.

Outside super-busy ares such as Le Plateau, Montreal reaches and maintains a respectful threshold of "vibrant" or "busy", but not crowded, (at least not crowded enough to make a standout impression on me).

This is where Chicago exceeds Montreal. I can visit MTL and see all the areas of "vibrant" or "busy" pedestrian activity within a few days, to the point where I've almost memorized them. They're conveniently located in a contigous area, and dont veer far from Metro stations, whilst Chicago has miles upon miles upon miles of vibrant pedestrian oriented neighborhood districts that aren't anywhere near the EL and often disconnected from a contigous experience. Its rare that visitors and tourists ever step foot in these areas. (Devon Street, Little Village, Belmont/Central, Clark Street in Rogers Park, Andersonville, 18th Street in Pilsen, Lawrence Ave in Albany Park, 79th Street on the South Side, etc) Chicago has endless streets after streets that flow into the horizon with "busy" foot traffic (Milwaukee, Clark, Belmont, Halsted, Lawrence, Lincoln to name a few) whereas Mont Royal, Sherbrooke, and St Laurent are the only ones I can think of for Montreal. At one point in Montreal the commercial activity just stops, and the major commercial streets turn into low rise residential avenues. Chicago keeps the vibrancy up to where theres a major walkable commercial street every half-mile (with the exception of the bungalow belt and slums). Toronto doesnt have this dynamic either.

OK, so thanks for the post and actually providing street names to have a look at on Streetview. I started from the bottom up, because I think you get a better feel for how strong the vibrancy is that way.

79th Street - I started East to West, S Greenwood to S Hoyne.

The Street is lined with commercial buildings, but there is a lot of boarded up and abondoned buildings. Very few actual businesses that would make the street vibrant. I would classify this street as a ghetto.

Lawrence Avenue in Albany Park - Once again, lots of commercial buildings, but a lot of boarded up storefronts, and very few businesses that would draw people out. Not as bad 79th, but not far off.

18th Street in Pilsen - it gets better here, because there is an actual stretch of bars and restaurants, though the density of those types of businesses is pretty light, and the rest of the street is spotty, and that goes for about 1.2 km's. That certainly doesn't stretch into the horizon.

So I only looked at the bottom 3 out of the 8 streets you named, because it's time consuming, but I get the impression that either Montreal or Toronto (having been to both cities multiple times, but not Chicago) are far more vibrant.

Even Vancouver might be more vibrant.

Doing a comparison of 18th Street in Pilsen in Chicago, and Commercial Drive in Vancouver, where 18th Street is 3.5 km's outside downtown Chicago, and Commercial Drive is 4 km's outside DT Vancouver, you will see Commercial Drive is far busier with bars and restaurants, coffee shops, etc., and it goes for 1.5 km's vs 1.2 for 18th Street.

Sure there are commercial building for miles in Chicago, but they are abandoned, or are used by a lot of industrial and wholesale businesses.

Anyways, just my take on it. Sorry to 🞵🞵🞵🞵 on Chicago. Go Cubs.

[shappy]

Originally Posted by softee

Toronto is much more vibrant in terms of pedestrian activity both downtown & in the old, pre-war urban neighbourhoods than Chicago. Only NYC is busier among cities in the U.S. & Canada. Of course this won't go over well among some of the forumers on here, but it's just reality now. It doesn't mean Chicago isn't a great urban city, it's just that Toronto has levelled up & passed it.

Have you been to Chicago? I was hoping the conversation would be a bit more nuanced than this.


This comment by Yuri stood out:

Originally Posted by Yuri

Chicago is definitely not that kind of city. I found it too well-kept, too wealthy, nothing edgy at all. I liked the city so much, that I overlooked this and really enjoyed the place.

It's a surprising observation and one that I don't believe I've heard about Chicago before. For those that have been, does this ring true? I felt that way about Boston, actually.

I don't think this is true for Canadian cities at all. Chicago is famously segragated which may speak to that? It could also be a more general cultural divergence between the two countries.

[Segun]

Originally Posted by softee

Toronto is much more vibrant in terms of pedestrian activity both downtown & in the old, pre-war urban neighbourhoods than Chicago. Only NYC is busier among cities in the U.S. & Canada, not counting the rest of the center of the country. Of course this won't go over well among some of the forumers on here, but it's just reality now. It doesn't mean Chicago isn't a great urban city, it's just that Toronto has levelled up & passed it.

Your "reality" simply isnt true. Are there any sources that prove what youre saying? Downtown employment, residents, commuters, visitors? Theres another forumer from Toronto in this thread that says the opposite. The more I think about it, I agree with him, mainly because of the sheer amount of domestic (not international) visitors to Chicago, which has been increasing ever year. Chicago is the "NYC" for a region thats has nearly the entire population of Canada, (not counting the rest of the center of the US). Street to street it might be the same. I think where Chicago might edge out Toronto are the massive crowds on the Lakefront, Navy Pier, Millennium Park, Museum Campus, and Riverwalk. Toronto has no comparison.

[Segun]

Originally Posted by logan5

OK, so thanks for the post and actually providing street names to have a look at on Streetview. I started from the bottom up, because I think you get a better feel for how strong the vibrancy is that way.

79th Street - I started East to West, S Greenwood to S Hoyne.

The Street is lined with commercial buildings, but there is a lot of boarded up and abondoned buildings. Very few actual businesses that would make the street vibrant. I would classify this street as a ghetto.

Lawrence Avenue in Albany Park - Once again, lots of commercial buildings, but a lot of boarded up storefronts, and very few businesses that would draw people out. Not as bad 79th, but not far off.

18th Street in Pilsen - it gets better here, because there is an actual stretch of bars and restaurants, though the density of those types of businesses is pretty light, and the rest of the street is spotty, and that goes for about 1.2 km's. That certainly doesn't stretch into the horizon.

So I only looked at the bottom 3 out of the 8 streets you named, because it's time consuming, but I get the impression that either Montreal or Toronto (having been to both cities multiple times, but not Chicago) are far more vibrant.

Even Vancouver might be more vibrant.

Doing a comparison of 18th Street in Pilsen in Chicago, and Commercial Drive in Vancouver, where 18th Street is 3.5 km's outside downtown Chicago, and Commercial Drive is 4 km's outside DT Vancouver, you will see Commercial Drive is far busier with bars and restaurants, coffee shops, etc., and it goes for 1.5 km's vs 1.2 for 18th Street.

Sure there are commercial building for miles in Chicago, but they are abandoned, or are used by a lot of industrial and wholesale businesses.

Anyways, just my take on it. Sorry to 🞵🞵🞵🞵 on Chicago. Go Cubs.

You didnt "🞵🞵🞵🞵" on anybody. Those neighbourhoods are far from the contigous area of walkability. My point was that they are disconnected and far from the core, so theres no comparable area in Montreal. If it was Toronto, you'd find yourself in area of wide 6 lane boulevards with highrises, with little connectivity between them. If it was Vancouver, it would be in the hinterlands. Despite the "gaps", its still a vibrant area with people out walking. Its still urban by any standard. Now try the same activity with Lincoln, Milwaukee, Halsted and Clark. Follow them from downtown to where they end. Those are the "horizon" streets in the core area, not from the first list.

[Segun]

Originally Posted by MonkeyRonin

It's been a while seen we've seen you around here! Always appreciate a post from an insider's perspective; and to your point we've all got our own biases (which naturally favour the Canadian cities in this forum). To some extent, arguing whether Chicago or Montreal or Toronto is more vibrant or urban is an act in splitting hairs - in the North American urban hierarchy New York is clearly in its own tier, while Chicago, San Francisco, Toronto, and Montreal are probably in a fairly evenly-matched second tier. I'd put Boston, Philly, DC, and Vancouver a tier below; then followed by the rest.

One of my favourite things about Chicago though is the massive scale and extent of its interesting, urban, pre-war neighbourhoods - from Evanston in the north to the South Shore, and out west to Forest Park. There are a ton of vibrant neighbourhoods with their own character - by sheer quantity, Chicago has any other non-NY city beat by a long shot. But, at the same time, the thing about all of these neighbourhoods is that they're somewhat disparate and disconnected; often separated by gaps in the urban fabric - whether that be freeways, abandonment, or industrial areas. There's simply a difference in experience of being able to walk for hours throughout continuously vibrant neighbourhoods versus ones where things sort of stop and start.

The other thing about all of Chicago's commercial strips is that there are simply too many of them relative to the population they support, so you get these sort of low intensity strips with a mix of businesses, residential buildings, and vacant storefronts. In Montreal and Toronto's case, there are fewer of these, so the ones that do exist are fuller and busier. Basically, Chicago is overbuilt; while Toronto and Montreal are underbuilt relative to their current populations. IMO, Chicago really needs a million or so more people for the human activity to match its built environment; whereas its Canadian counterparts have a sort of teeming quality today because they simply were never planned or built to house as many people as now reside in them.

The other area where Chicago really shines though, is in the Loop, which is easily the most impressive downtown core outside of Manhattan. Toronto isn't quite at the same level, while Montreal's downtown is still a long ways off.

This I can see.

Whenever I visit Toronto or Montreal, I find the amount of foot traffic in comparison to the scale of the street remarkable. You have streets of small businesses and lowrises teeming with foot traffic. This is perhaps why someone might feel as if downtown Toronto and or Montreal is busier. The traffic doesnt match the scale, so psycologically it might feel more "packed" The same goes for the Tenderloin, North Beach in San Francisco.

Chicago does have areas like this (Clark/Diversey, Milwaukee/North, Clark/Belmont), but they are too far from downtown to pickup overflow from the Loop and Michigan Avenue.

It begs the question though. Is it more urban and vibrant to have super-busy areas of commerce funneled into a few streets, or busy areas spread out across the city? I think its about the same. Btw, I agree with your tiered list.

Chicago at its height was denser than SF is today at 220 Sq miles (and way less residential highrises, it was all low rise density) Chicago is seeing a Renaissance, so the probability of it filling its infrastructure, filling its gaps is on the table. It doesnt take as much effort to renew urbanity as it does to construct new urbanity. It should be interesting to see.