The Caribbean in $210s-$330s RT
Black Friday is churning along, and we've got a nice set of non-stop hops right down to the Caribbean.
While most of you get the beautiful bioluminescent shores of Puerto Rico or the shores of some untouched islands, our friends in New York are the belles of the ball today! Between Saints Vincent & Lucia, or Antiguas & Barbudas, your upcoming island getaway is filled with nothing but places that'll make you go doo-dah!
Let's hope for more good tidings for the rest of us this Black Friday season 
Taking off ✈️
Tip Published: Nov 24, 2025
Round trips from Boston (BOS):
- Nassau (NAS) - $310
- Saint Thomas (STT) - $234
- San Juan (SJU) - $202
- Sint Maarten (SXM) - $339
Round trips from Chicago O'Hare (ORD):
- San Juan (SJU) - $218
Round trips from New York (JFK):
- Basseterre (SKB) - $282
- Bridgetown (BGI) - $337
- Kingstown (SVD) - $306
- Nassau (NAS) - $330
- Saint Lucia (UVF) - $313
- Saint Thomas (STT) - $210
- Santiago (STI) - $323
- Santo Domingo (SDQ) - $327
- Sint Maarten (SXM) - $303
- St. John's (ANU) - $305
Round trips from Philadelphia (PHL):
- San Juan (SJU) - $224
How to Book
This is a Takeoff-only Flight for Jack's Flight Club Takeoff members only. For step by step instructions on how to book it you'll need to login or upgrade to Takeoff membership.
