Southwest has many deals and cities to chose from with prices starting at $59 one way. The travel dates vary depending on the cities you pick. From the U.S. travel between

  • Domestic travel valid December 27, 2016 through May 8, 2017. Travel to/from San Juan, Puerto Rico valid January 17, 2017 through March 2, 2017 and April 18, 2017 through May 8, 2017.
  • International travel valid January 10, 2017 through March 2, 2017 and April 18, 2017 through May 8, 2017.

To take advantage of this deal you must book your travel by December 15th..

southwest-dec2016

 

From Atlanta, GA example of some great deals (but on there site you can see the complete list)

From Hartford, CT

there is even some great deals to Havana, CUBA..

From Havana, Cuba

there is even some great deals to Jamaica as well..

From Montego Bay, Jamaica

Many cities to chose from..