The Caribbean 
in $270s-$490s RT
FLIGHTS HOOOO!!!
Hold fast, ye scurvy dogs! Cap'n Jack just spotted some fine Caribbean fares from the ol' crow's nest. There's many a fair port represented in this here bundle, from Aruba's white sands to the pirate stronghold of Nassau, each one fit for landlubbers and salty travelers both.
So let fly yer itinerary, pack yer booty in the carry-on, and remember to drink plenty of rum 
Taking off ✈️
Tip Published: Oct 20, 2026
Round trips to Anguilla (AXA):
- Atlanta (ATL) - $497
Round trips to Aruba (AUA):
- Las Vegas (LAS) - $486
- Miami (MIA) - $337 (non-stop)
- Tampa (TPA) - $288
- Washington Reagan (DCA) - $342
Round trips to Curaçao (CUR):
- Las Vegas (LAS) - $477
- San Diego (SAN) - $483
Round trips to Grand Cayman (GCM):
- Baltimore (BWI) - $337
- Washington Reagan (DCA) - $342
Round trips to Grenada (GND):
- Boston (BOS) - $492
Round trips to La Romana (LRM):
- Austin (AUS) - $390
- Chicago (ORD) - $400
- Washington Reagan (DCA) - $370
Round trips to Montego Bay (MBJ):
- Sacramento (SMF) - $493
- San Francisco (SFO) - $466
- Washington Reagan (DCA) - $355
Round trips to Nassau (NAS):
- Austin (AUS) - $306
- Las Vegas (LAS) - $306
- San Francisco (SFO) - $366
Round trips to Providenciales (PLS):
- New York (JFK) - $393 (non-stop)
Round trips to Punta Cana (PUJ):
- Austin (AUS) - $390
- Chicago (ORD) - $396
- Los Angeles (LAX) - $390
- San Francisco (SFO) - $452
- Washington Reagan (DCA) - $370
Round trips to Saint Croix (STX):
- Austin (AUS) - $474
- Boston (BOS) - $420
- Los Angeles (LAX) - $492
- San Antonio (SAT) - $482
Round trips to Saint Thomas (STT):
- Las Vegas (LAS) - $418
- New York (JFK) - $337 (non-stop)
- Palm Beach International (DJT) - $298
- Phoenix (PHX) - $440
Round trips to San Juan (SJU):
- Houston (HOU) - $396
- Houston (IAH) - $396
- Las Vegas (LAS) - $270
- Los Angeles (LAX) - $290
- Sacramento (SMF) - $458
- San Jose (SJC) - $458
Round trips to Santiago (STI):
- Chicago (ORD) - $426
- Tampa (TPA) - $346
- Washington Reagan (DCA) - $354
Round trips to Santo Domingo (SDQ):
- Austin (AUS) - $324
- Chicago (ORD) - $378
- Dallas (DFW) - $418
- Philadelphia (PHL) - $314 (non-stop)
- Tampa (TPA) - $358
- Washington Reagan (DCA) - $402
Round trips to Sint Maarten (SXM):
- Austin (AUS) - $351
- Miami (MIA) - $356 (non-stop)
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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.
