When is the cheapest travel time internationally? To Jamaica, Mexico, Punta Cana, etc?

Looking to schedule our vacation for this year and was wondering when the low season or best deals to these kind of destinations typically are. I know right now the prices are high since everyone wants to be in the warm weather - so when are the best deals? Summer? Fall?

Either spring or summer!!

Well I'm from Jamaica and I work in the tourist industry. Winter and Summer seasons are usually the 'peak seasons'. I wouldn't say the prices are higher during this time though because there are a number of specials being offered. It is usually the off-peak seasons when the hotels don't have much 'people traffic' that the prices seem higher as there aren't much deals being offered. Normally the best time to recieve good deals are between December and April.

For example, I work at the Half Moon Resort and Spa in Montego Bay. For the winter season, we currently have a 'Winter Escape Package'. This package will run from Jan. 5th - April 17th. During this period, if you stay a minimum of 5 Nights you and receive:
- $200 Resort Credit per room
- Daily breakfast for fully paid adults,
- Round trip airport transfers

Plus:
- Kids under 12 Stay Free with Daily breakfast when sharing room with 2 parents (maximum 2 children)
- 50% off any meal plan for children under 12 years of age
- Special Single Parent rate. (Single rate with children under 12 years old, maximum 2 children)

Blackout dates:
February 14 - 22, 2007.

You can check out the specific rates at our website which is www.halfmoon.com. We also offer several offer packages to suit your needs.

See you in Jamaica soon :)

Cheapest time is during the fall, Sept. to Dec. 15, omiting Thanksgiving. It is hurricane season then, but like this year, there really wasn't one. The next lowest time if middle of April to middle of May, after spring break and before the summer season.
Weather is nice year around. Summer can be cheap if you live in a place that has a charter which is usually less than regular airfare which usually comes down to compete with them.