5 Major US Cities And Their Canadian Equivalents

Ever wonder what the Canadian version of San Francisco might look like? How about the American version of Winnipeg?

If you're among the many Americans and Canadians who love drawing similarities between their own cities and those across the border, good news: We've narrowed down five U.S. cities and Canadian cities that are most similar to one another. Read on!

New York and Montreal

Of all the cities in this list, none share more in common than New York and Montreal. Both were founded within about a decade of one another, were the largest and most important cities in their respective countries (until the 1980s, in Montreal's case) and remain to this day the most densely populated cities in each.

Montreal and New York also share a number of visual parallels: Art Deco architecture is common in both (compare, for example, the Aldred Building and the Université de Montréal in Montreal to New York's Chrysler Building) and the centers of both cities are defined by a grid system of one-way streets.

The two cities also have the highest populations of college-aged students per capita in North America, which is partly the reason each is known for its lively nightlife. Speaking of which, Montreal largely owes its reputation as a party city to the Big Apple: hedonists, jazz musicians, and gangsters who fled north during Prohibition helped popularize the nickname ‘Harlem of the North’ for Montreal.

If that weren't enough, Montreal and New York, being popular destinations for Yiddish immigrants at the turn of the 20th century, are both known for their unique versions of the bagel.

And when it comes to organized crime, the historical ties between the two towns is well-documented: The Mafia had a stronghold in both cities since the 1920s. The Montreal faction grew considerably in the 1980s after the arrival of Vito Rizzuto, who fled north from New York after being involved in a major dispute with members of the Bonnano crime family in 1981.

Toronto and Los Angeles

Toronto and Los Angeles are nearly the same age: The former was established in 1787, less than twenty years after the latter. For more than a century, each city saw sluggish growth before an explosive spurt placed both cities among the largest in their respective countries. Today, Toronto is Canada's biggest city, and L.A. is America's second.

Both cities are also popular destinations for Asian immigrants, who make up just under 30% of the population in each. Each city is the biggest manufacturing hub in its respective country, and each has a huge film and TV industry.

In terms of architecture, the two towns share a very special connection: Frank Ghery, the world-renowned architect who was born in T.O. and resides in L.A., has iconic buildings in both cities: The Art Gallery of Ontario on Dundas Street and the under-construction Forma condo on King Street are both among Toronto's most notable structures, while L.A. is known for its Walt Disney Concert Hall on Grand Avenue.

But perhaps the biggest commonality the two cities share is traffic. The 405 in L.A. is the busiest highway in the U.S., while Toronto's 401 is the busiest in Canada.

Vancouver and San Diego

San Diego shares more than a few similarities with Vancouver: Both cities are within a few miles of an international border. Both offer an idyllic climate compared to virtually anywhere else in their respective countries (Vancouver is one of the only cities in Canada that rarely sees snow). And both offer vast stretches of beach along the Pacific Coast.

The two towns have also long been known as havens for hippies. Newport Avenue is the heart of San Diego’s hippie culture, much the same as Fourth Avenue is Vancouver’s.

But the laid-back lifestyle each city is associated with is what makes Vancouver and San Diego most alike. For evidence of the live-and-let-live mentality that defines each city, check out Black’s Beach in San Diego, or Wreck Beach in Vancouver: both are among the largest publicly-maintained nude beaches in North America, along with Crescent Rock Beach (Vancouver) and Torrey Pines State Beach just north of San Diego.

Winnipeg and Chicago

There are a number of reasons Winnipeg is known as “Chicago of the North” and "Little Chicago." The two cities are both located near the geographical center of their respective countries. In addition to being major prairie cities and important transportation hubs, they also share more similarities on the architectural front: John Danley Atchinson, an American architect educated at the Chicago School of Architecture, spent years in Winnipeg and influenced the design of many of the city's most notable structures, such as the Curry Building and the Maltese Cross Building.

But one of Winnipeg's most well-documented connections to Chicago comes during Prohibition. Al Capone's criminal enterprise extended all the way from Chicago to Winnipeg's Exchange District, below which tunnels were built to allow booze to be smuggled across the border, forever solidifying the two cities in a sinister saga that still fascinates today.

St. John’s and San Francisco

St. John's, Newfoundland and San Francisco are known in their respective countries for their wet and foggy weather and relatively cooler summers. But that’s not all the two cities have in common. Both are also known for their steep inclines: Check out Bradford Street and Filbert Street in San Fran, or Holloway Street and King Street in St. John’s, which are among the hilliest streets in North America. That, combined with the seemingly endless stretches of colourful Victorian homes that define each city’s landscape, makes St. John’s and San Francisco nearly indiscernible from one another at first glance.

Distinct yet closely connected

Canada and the U.S. share far more in common than the world’s longest international land border. With two-thirds of Canadians living within 100 kilometers of the border, Canada and the U.S. are about as close as two countries can be, geographically and culturally speaking. Despite being two distinct countries with their own unique histories, their close proximity has bound them inextricably together as neighbours and partners whose similarities far outweigh their differences.