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Location: Montreal
Climate: Chicago
Scenery/Architecture: different but Chicago has the edge
Quality of life: Montreal
Safety: Montreal by far
Public transportation: both are good. Chicago has more rapid lines
Shopping: Chicago
Universities: Chicago
Entertainment/Things to see and do: Montreal
Diversity: Chicago
Economy: not sure, maybe Chicago
Culture/Food/History:Montreal
Chicago is probably better in regards to Diversity as well as Language alone (You'll probably be criticized unless you are at least partially fluent in French). Chicago also has plenty of culture and great diverse food options like deep dish pizza, damn its good. I'm sure Chicago has more places you should avoid than Montrael with regards to safety, but as long as you stay in either the downtown area or the North Side, and avoid the west and south sides like the plague, you should be A OK. I'm not sure about Montrael's transportation, but Chicago has probably the best services for transportation out of every city in America, at least in my opinion. The CTA is very competent and runs through the whole city. If you speak English I'd say Chicago.
In my opinion overall i like Chicago better than Montreal, and i am Canadian btw... Location: Montreal has a lot of hills from what i know, and has a lot of trees and scenery (nature) Chicago has the bay front on Lake Michigan
Climate: I like the Chicago "Windy-City" feel, although it's known for the rain i think it really feels good for Chicago with the high skyline and nice downtown wind breeze.
Scenery/Architecture: Chicago for sure has a lot more visually appealing architecture/scenery especially in downtown.
Quality of life: Montreal rates as one of the best in North America, as if you aren't aware, every Canadian has access to Universal Care (free, although we pay taxes), communities are also a lot safer, meaning less gangs, guns, and violence in Montreal...
Safety: Again, less violence in Montreal, although crimes like robbery and stuff like those occur everywhere.
Public transportation: Not sure, i know that Montreal has a great transportation system though and lots of Canadians rely on this which is a good thing (less cars, less carbon released from cars)
Shopping: It is a tie, Chicago has a lot of well known high-class American/European shops in downtown, Montreal is similar, probably a lot of french...
Universities: Not sure....
Entertainment/Things to see and do: They are both amazing cities, Chicago though has a lot more interesting things to see such as the nice bridges in the downtown core with the lovely stream that flows into L.Michigan...
Diversity: Montreal
Economy: Montreal
Culture/Food/History: Chicago has a lot more cultures, variety of restaurants to offer from than Montreal does even though it is a Canadian city and Canada is known for being "Multi-Cultural"
In my opinion overall i like Chicago better than Montreal, and i am Canadian btw...
Climate: I like the Chicago "Windy-City" feel, although it's known for the rain i think it really feels good for Chicago with the high skyline and nice downtown wind breeze.
Chicago is known for its climate but I don't think people think of rain when they think of Chicago. If anything it's cold and snow.
Chicago is not the windiest city in the United States: Milton, Massachusetts is. Chicago is not significantly windier than any other U.S. city. For example, the average annual wind speed of Chicago is: 10.3 mph (16.6 km/h); Milton is: 15.4 mph (24.8 km/h); Boston: 12.4 mph (20.0 km/h) New York City, Central Park: 9.3 mph (15.0 km/h); and Los Angeles: 7.5 mph (12.1 km/h).
Chicago is not the windiest city in the United States: Milton, Massachusetts is. Chicago is not significantly windier than any other U.S. city. For example, the average annual wind speed of Chicago is: 10.3 mph (16.6 km/h); Milton is: 15.4 mph (24.8 km/h); Boston: 12.4 mph (20.0 km/h) New York City, Central Park: 9.3 mph (15.0 km/h); and Los Angeles: 7.5 mph (12.1 km/h).
The nickname is most likely not weather related.
The nickname came from boasting local politicians did to land the World's Columbian Exposition in 1893. The "Windy City" name was given to Chicago by a New Yorker working at the New York Sun. I don't know why people keep getting this confused.
There is no consensus of its origin on the interwebs. There are multiple 'theories' and that is one of them, but there is just about a general consensus that it has nothing to do with wind.
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