Came across this great flight deal and had to share:
Chicago to Barbados
$265 round trip on Jet Blue
Dates: various in January and February 2017 (3-10 nights)
To buy: go to http://www.priceline.com. Enter the airport codes (ORD, BGI) and enter dates within the range.
**Price typically only valid 48 hours**
I suggest Air BnB for lodging to save money. These months tend to be more expensive for hotels in The Caribbean since most people are seeking Winter escapes.