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Montreal - Boston - Historically, Montreal and Boston were among the most important cities when settlers first arrived and both cities played major roles in the founding of their respective countries.

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Montreal - Philadelphia - The walkability of these cities is a stand-out feature you feel in few other places in North America.

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Montreal - Brooklyn, New York - The counter-culture, the highly fashionable population, large Caribbean influence, and aggressively friendly inhabitants make these two artistic hubs similar.

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Toronto - Manhattan, New York - These cities are constantly compared with each other, partly because of their proximity, hyper-competitive cultures, financially-driven mindset, and being the biggest population centres of their respective countries.

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Toronto - Chicago - These two cities have almost the exact same population, with Toronto recently surpassing Chicago to become the fourth-largest city in North America.

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Toronto - Los Angeles - The climate is obviously different in these two cities, but Toronto's reputation as 'Hollywood North' (stolen from Vancouver) on top of its reputation as being superficial bring out interesting commonalities with LA.

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Toronto - Atlanta - Although Toronto is far bigger than Atlanta, a musical connection between the two cities over the past decade has created some of the biggest recording artists in this generation.

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Toronto - Miami - It may seem like a strech, but Miami's architecture looks shockingly like the new buildings sprouting up all over Toronto. The two vastly different cities have a similar amount of skyscrapers.

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Vancouver - Portland - The west coast spirit is alive and well in these two hipster, yoga-loving cities. If the Toronto - New York comparison is a cliché, then the Vancouver - Portland one is its western counterpart.

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Vancouver - Seattle - They're the major Pacific city centres of their respective countries and known for thinking differently than the rest of their countries. 

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Vancouver - Los Angeles - They're the centres for film making, even if Toronto and New York take all the credit. Vancouver and LA enjoy their countries' best weather, mountain views, Pacific coast beaches, and laid-back vibes.

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Vancouver - San Francisco - Both these cities have the distinction of having the highest real estate prices in their countries. They're both also known for having progressive values.

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Calgary - Denver - These Rocky Mountain cities are famous for bragging about how clean their tap water is. 

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Calgary - Dallas - Cowboy country's major urban centres are known for their wealthy, resource-rich inhabitants and major population growth.

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Calgary - Atlanta - These two cities have outsized cultural impacts on their countries, despite not being the biggest. 

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Edmonton - Houston - Edmonton and Houston are known for being the alternative siblings to their larger neighbours in Calgary and Dallas.

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Edmonton - Minneapolis - Edmonton is often referred to as a smaller Minneapolis because of the riverside topography and sports-obsessed population.

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Edmonton - Denver - These mountain towns are both geographically isolated from the rest of their respective countries.

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Quebec City - New Orleans - These New French settlements share similar old architecture, but have vastly different interpretations of their French heritage.

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Quebec City - Philadelphia - These historical cities were among the first major European settlements in North America and still bear the architecture from that time. 

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Halifax - Boston - Both of these cities were once major ports of New England during the colonization of North America.

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Halifax - Portland - The cultures of seaside living and street food are alive and well in these cities.

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Moncton, New Brunswick - Bangor, Maine - These two nearby Atlantic towns are known for being the biggest proximity to wooded wilderness and great fishing. 

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Ottawa - Washington, D.C. - The capitals of Canada and the US are an easy comparison for their large international community and high infrastructure spending.

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Hamilton, Ontario - Pittsburgh - These two steel towns are both seeing major resurgences as cultural centres, in part due to their affordable real estate.

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Hamilton, Ontario - Brooklyn, New York - Hamilton is often called the Brooklyn of Canada because the former is Toronto's often overlooked, edgier, and cheaper neighbour.

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Hamilton, Ontario - Philadelphia - Both these cities bring to mind the word "grit," but they've also produced some major contributions in music and the arts.

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Winnipeg - St. Louis - The gateways to the west, Winnipeg and St. Louis straddle the Great Lakes region and the Prairies. 

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Niagara Falls - Las Vegas - They're amusement park cities, and while Las Vegas is far larger and more famous, Niagara offers its own wild rides. 

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