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Any city that can be the butt of a Simpson's joke ("That's it! We're all going back to Winnipeg!") and simultaneously one of the most vibrant cultural centers in Canada is tops in our book. The city's history of isolation and self-sufficiency means that Winnipeggers are unpretentious and sincere (and fun-loving enough to name Homer an honorary citizen). Though the winters are long and cold, there are plenty of indoor activities to both keep you warm and stimulate your imagination.
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*Prices are based on 1-21 day travel. These are the best fares found by travelers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.