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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.
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Before getting there I was afraid Chicago wide streets would bother me a lot. At least on the Loop, however, due the sheer size of the skyscrapers, wide sidewalks, they didn't feel hostile, but quiet cozy.
And they have very nice urban neighbourhoods such as Lincoln Park, Old Town, Andersonville, Wicker Park. All very beautiful and welcoming. Montreal residential neighborhoods probably are denser though.
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Originally Posted by MolsonExport
If you enjoyed Berlin, you will very likely enjoy Montreal. It shares a lot of similarities, in terms of eclecticism, vibrancy, size, and especially, bohemianism. There is still a fair bit of grit, although nothing compared to what you would find in the late 90s.
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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. I could even see me living there, something I only felt about London before.
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Originally Posted by Nouvellecosse
They seem to be separate things in your case at least. Perhaps that's why it feels contradictory to hear you say that as a tourist you have no interest in visiting parts of a city outside the downtown or cool inner city districts. When I'm visiting a new place I want to explore and learn about as much of the city as i can, and that includes places not popular with tourists. I don't always have time, but i always have the interest. It makes sense with Sao Paolo since you probably have explored the rest of the city before and already know whether you'd enjoy spending time there. But for someone visiting an unfamiliar city it's hard to understand how it's interesting to see stats on the internet but not actually exploring directly.
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There's another thing: money and specially time. My vacations are not flexible and not very long, so I must be very picky. If those were not factors, I'd definitely go very deeper, even into "non-interesting" places.
And of course, I'll do plenty of stuff out of the touristic stuff, that I don't like at all aside to see the basics. For instance, in Amsterdam I didn't go to Red Light District but I explored the LGBT nightlife there, out of the touristic circuit. In Belgium, I picked Antwerp over Bruges.
I had my phase of explorer when I was younger: I toured once for all mid-sized cities upstate São Paulo and they couldn't be less touristic. Today I've became even more unconfortable outside very big cities and I'm more aware of time. Hence I didn't go up to Milwaukee as Chicago had more to offer and I didn't want to waste even a single day.