Chicago

Chicago is the megalith of America's Midwest. Hyper-important as a regional hub for surrounding farmland, towns, and cities, Chicago also serves as a major international tourist destination for amazing food, for the active comedy, theatre, and arts scene, and for the city's imposing figure itself. Chicago also loves hockey, loves drinking, and hates you if you don't agree.

Portland

Portland is America's center for Voodoo Donuts, old-man sweaters, an unwieldy amount of strip clubs, open water reservoirs, and cocaine. They also have great food, access to amazing outdoor experiences, and a pretty positive attitude, considering the crap climate. Maybe they're just all on drugs. Sounds like Montreal?

Austin

Austin is a pretty neat place. Famous for S/SW, tattoos, facial hair and innovative cuisine, this place manages to hold titles of capital of Texas and Brooklyn of the West simultaneously. Austin is renowned for its music scene, bar scene, and having that concealed carry "make my day" attitude often found in the East!

Omaha

People in Montreal might of never heard of Omaha, Nebraska, and we can't blame them. But that doesn't mean it isn't a kindred spirit in many ways. Omaha is a bedrock of funk, jazz, blues, ragtime, and rock music. Like Montreal, it also is a city with great importance to the surrounding rural farmland for food processing and agriculture business.

Minneapolis-St. Paul

Just like Montreal is often lumped in with Laval, or even Ottawa, in certain surveys and assessments, and in conversation, we bring you the metropolitan area of Minneapolis-St. Paul. They love hockey, the weather is abysmal, they sound like Ontarians, and they love mayonnaise. What more is there? Minneapolis is also a lovely city with some great restaurants, parks, nearby lakes, and important technology industries like Montreal.

Philadelphia

Philly makes it onto this list because it's close, it's a similarish (bigger though) size, and it shares two of Montreal's important features: disappointing sports teams, and that gritty East Coast demeanor worn deep through season after season of bitterly drunk winters.

San Francisco

Calling San Francisco a sister city of Montreal is being kind...to SF! Psych. SF has world class cuisine, art, and vistas -- a row-house mega city sprawled out over lush green hills laid at the mouth of the bay. SF brings you close to Red Wood forests, great Mexican food, the beaches of Carmel and amazing wildlife in the ocean. Montreal does share the essential mindset and ethos of SF, however, and embraces cuisine, nature, and art, in its own beautiful way.

Cleveland

Cleveland is in the news these days for sports: the return of LeBron, Johnny Manziel begins with the Browns, and Canadian phenom Andrew Wiggins takes off with Bron's Cavs. Before this, however, Cleveland had more in common with Montreal. Cities not on the coast, but not in Kansas either, of middling size, of crap weather, and of important (if declining) industries. Cleveland has fight in it, and was an important place in the Prohibition liquor smuggling between Canada and the US, so it's on the list.

New York

Comparing Montreal to New York is like the SF comparison, silly perhaps, but apt in certain ways. New York shares Montreal's history of being a new home for countless immigrants. Many important connections between Jewish, Irish, English, Dutch, German, and French families were formed between Montreal and New York historically. Today, the symbiotic relationship between Montreal and New York continues, as seen in transplanted Montreal bagel businesses like Black Seed Bagels, and similar movements in the food, bar, and art worlds.

Atlanta

Atlanta is a party -- let me tell you. Whether you're looking for a wild night at a club (which in Atlanta means strip club), a nice restaurant, A+ BBQ, peach cobblers, etc., Atlanta is the place for you. Like Montreal, Atlanta also is home to many new citizens from West Africa and has a thriving West African and Caribbean food scene.

New Orleans

New Orleans share's Montreal's French legacy, as the same 16th-century colonial folks that settled in Quebec made their way down to what is now Louisiana and established a culture there. French culture is still very important in New Orleans, in food, art, music, etc., and French words are still mixed in with Cajun and English words in parts of Louisiana to form the common lexicon.

Sign up for your chance to win 2 tickets for a flight to one of these cities, or any US city of your choice.

Where will you chose to go?