All Around the Caribbean 
in $240s-$340s RT
The Caribbean is all about SOUND.
The soundĀ of maracas shaking all around. TheĀ soundĀ of waves lightly lapping onto the shore right at dawn. And the soundĀ of your keyboard click-clacking to book these Flights before they go away :-)
We're especially stoked to see some uber-rare routes pop up (like first timeĀ EVERĀ kind of rare). Looking at you, La Romana, with almost every city in here seeing you for the first time. Show 'em what you got.Ā
Did we mention sound?Ā
Taking off āļø
Tip Published: Sep 10, 2025
Round trips from Atlanta (ATL):
- Punta Cana (PUJ) - $309
- Saint Croix (STX) - $316
Round trips from Austin (AUS):
- Aruba (AUA) - $295
- Grand Cayman (GCM) - $286
- La Romana (LRM) - $336
- Punta Cana (PUJ) - $309
- Santiago (STI) - $325
- Santo Domingo (SDQ) - $327
- Sint Maarten (SXM) - $297
Round trips from Boston (BOS):
- Aruba (AUA) - $341
- Nassau (NAS) - $330 (non-stop)
- Puerto Plata (POP) - $325
- Punta Cana (PUJ) - $336
- Saint Lucia (UVF) - $337
- Santiago (STI) - $311
Round trips from Fort Lauderdale (FLL):
- Kingston (KIN) - $299 (non-stop)
- Montego Bay (MBJ) - $299 (non-stop)
- Nassau (NAS) - $240 (non-stop)
- Punta Cana (PUJ) - $242 (non-stop)
- Saint Croix (STX) - $259
- Saint Thomas (STT) - $259
- Santo Domingo (SDQ) - $240 (non-stop)
Round trips from Miami (MIA):
- Aruba (AUA) - $297 (non-stop)
- Grand Cayman (GCM) - $295 (non-stop)
- Kingston (KIN) - $307 (non-stop)
- Nassau (NAS) - $250 (non-stop)
- Port of Spain (POS) - $294 (non-stop)
- Saint Croix (STX) - $286 (non-stop)
- Santiago (STI) - $263 (non-stop)
Round trips from New York (JFK):
- Aruba (AUA) - $281 (non-stop)
- Basseterre (SKB) - $307 (non-stop)
- La Romana (LRM) - $297
- Providenciales (PLS) - $329 (non-stop)
- Puerto Plata (POP) - $320 (non-stop)
- Saint Croix (STX) - $286
- Saint Lucia (UVF) - $327
- Santiago (STI) - $316 (non-stop)
- Sint Maarten (SXM) - $321 (non-stop)
Round trips from New York (LGA):
- Aruba (AUA) - $339
- Basseterre (SKB) - $322
- Grand Cayman (GCM) - $336
- Puerto Plata (POP) - $327
- Saint Croix (STX) - $286
- Santo Domingo (SDQ) - $331
- St. John's (ANU) - $349
Round trips from Newark (EWR):
- Aruba (AUA) - $281 (non-stop)
- Basseterre (SKB) - $307 (non-stop)
- Bridgetown (BGI) - $341 (non-stop)
- La Romana (LRM) - $297
- Saint Lucia (UVF) - $313 (non-stop)
- Santiago (STI) - $316 (non-stop)
Round trips from Orlando (MCO):
- La Romana (LRM) - $311
- Nassau (NAS) - $280 (non-stop)
- Saint Croix (STX) - $271
- Santiago (STI) - $303
- Santo Domingo (SDQ) - $326 (non-stop)
Round trips from Tampa (TPA):
- Aruba (AUA) - $261
- Grand Cayman (GCM) - $286
- Montego Bay (MBJ) - $319
- Saint Croix (STX) - $291
- Santiago (STI) - $323
- Santo Domingo (SDQ) - $328
- Sint Maarten (SXM) - $295
Round trips from Washington DC (DCA):
- Nassau (NAS) - $335
- Punta Cana (PUJ) - $335
- Saint Croix (STX) - $311
- Santo Domingo (SDQ) - $336
Round trips from Baltimore (BWI):
- Saint Croix (STX) - $325
Round trips from Las Vegas (LAS):
- Saint Croix (STX) - $305
How to Book
This is a Premium deal for Jack's Flight Club members only. For step by step instructions on how to book it you'll need to login or upgrade to Premium membership.
