Calgary, Canada

Calgary, a cosmopolitan Alberta city with numerous skyscrapers, owes its rapid growth to its status as the centre of Canada’s oil industry. However, it’s still steeped in the western culture that earned it the nickname “Cowtown,” evident in the Calgary Stampede, its massive July rodeo and festival that grew out of the farming exhibitions once presented here.

Increase in searches: 26%
Cheapest month to fly: October
Best time to book: Three months in advance

Havana, Cuba

Increase in searches: 191%
Cheapest month to fly: November
Best time to book: Two months in advance

San Francisco, CA