Caribbean 
in $230s-$490s RT
OliviaJFC
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This pile of Caribbean fares towers higher than Pico Duarte, so let's break it down! There's a tropical beach vacation for everyone in here.
Highlights in this list include....
- The perennially popular spots that need no introduction — the "name-dropped in 'Kokomo'" crowd. Aruba, Jamaica, Key Largo, Bahamas, you know the drill.
- A surprisingly hefty amount of fares to the much more rarely seen island of Grenada, where they don't mess around when it comes to spices.
- Routes to both of the larger US Virgin Islands (I preferred St. Croix and their rum distillery, personally, but Thomas has some pretty unbeatable coastal views).
- A few fares to both Barbados and Antigua, which are the two stunning islands at the top of my Caribbean to-do list. If you snag trips to either of those, be sure to send us a postcard so I can seethe with envy :-)
Taking off ✈️
Tip Published: Aug 05, 2026
Round trips to Aguadilla (BQN):
- Atlanta (ATL) - $282
- Boston (BOS) - $318
- Los Angeles (LAX) - $342
- Philadelphia (PHL) - $321
- Phoenix (PHX) - $327
Round trips to Aruba (AUA):
- Boston (BOS) - $381 (non-stop)
- Los Angeles (LAX) - $429
- Orlando (MCO) - $443 (non-stop)
- Philadelphia (PHL) - $483 (non-stop)
- San Francisco (SFO) - $499
Round trips to Bridgetown (BGI):
- Boston (BOS) - $452 (non-stop)
- New York (JFK) - $446 (non-stop)
- Newark (EWR) - $446 (non-stop)
Round trips to Cayman Brac (CYB):
- New York (JFK) - $467
Round trips to George Town (GGT):
- Atlanta (ATL) - $489 (non-stop)
Round trips to Grand Cayman (GCM):
- Austin (AUS) - $387
- Denver (DEN) - $452
- Las Vegas (LAS) - $477
- Los Angeles (LAX) - $487 (non-stop)
- Miami (MIA) - $287 (non-stop)
- Orlando (MCO) - $477 (non-stop)
- Sacramento (SMF) - $477
- San Diego (SAN) - $477
- Tampa (TPA) - $321 (non-stop)
Round trips to Grenada (GND):
- Baltimore (BWI) - $467
- Denver (DEN) - $457
- Las Vegas (LAS) - $457
- Los Angeles (LAX) - $457
- New York (JFK) - $430 (non-stop)
- San Diego (SAN) - $469
- San Francisco (SFO) - $476
- Washington Dulles (IAD) - $467
- Washington Reagan (DCA) - $467
Round trips to Key West (EYW):
- Washington Dulles (IAD) - $299 (non-stop)
Round trips to Kingston (KIN):
- Philadelphia (PHL) - $461
Round trips to Kingstown (SVD):
- Boston (BOS) - $427
- Los Angeles (LAX) - $475
- New York (JFK) - $381 (non-stop)
- San Diego (SAN) - $463
- Seattle (SEA) - $487
Round trips to Montego Bay (MBJ):
- Boston (BOS) - $418 (non-stop)
- Los Angeles (LAX) - $472
- Portland (PDX) - $452
- Sacramento (SMF) - $432
- San Diego (SAN) - $492
- Tampa (TPA) - $320 (non-stop)
Round trips to Nassau (NAS):
- Boston (BOS) - $401 (non-stop)
- Dallas (DFW) - $388 (non-stop)
- Denver (DEN) - $401
- Las Vegas (LAS) - $341
- Los Angeles (LAX) - $390
- Philadelphia (PHL) - $425 (non-stop)
- Phoenix (PHX) - $431
- Salt Lake City (SLC) - $493
- San Diego (SAN) - $494
- San Francisco (SFO) - $401
Round trips to Port of Spain (POS):
- Atlanta (ATL) - $430
- Boston (BOS) - $412
- Chicago (ORD) - $472
- Las Vegas (LAS) - $467
- Los Angeles (LAX) - $456
- Miami (MIA) - $287 (non-stop)
- Phoenix (PHX) - $466
- Salt Lake City (SLC) - $448
- San Diego (SAN) - $444
Round trips to Providenciales (PLS):
- Austin (AUS) - $419
- Boston (BOS) - $371 (non-stop)
- Fort Lauderdale (FLL) - $429
- Miami (MIA) - $439
- New York (JFK) - $411 (non-stop)
- Orlando (MCO) - $482 (non-stop)
- Sacramento (SMF) - $481
- San Diego (SAN) - $481
- Washington Reagan (DCA) - $377
Round trips to Puerto Plata (POP):
- Los Angeles (LAX) - $480
Round trips to Punta Cana (PUJ):
- Boston (BOS) - $415 (non-stop)
- Houston (IAH) - $468
- Los Angeles (LAX) - $480
- Miami (MIA) - $275 (non-stop)
- Newark (EWR) - $315 (non-stop)
- Orlando Sanford (SFB) - $267 (non-stop)
- Tampa (TPA) - $367 (non-stop)
Round trips to Saint Croix (STX):
- Atlanta (ATL) - $447 (non-stop)
- Denver (DEN) - $428
- Miami (MIA) - $263 (non-stop)
- Orlando (MCO) - $352
- Philadelphia (PHL) - $476
- San Diego (SAN) - $466
- Tampa (TPA) - $312
Round trips to Saint Thomas (STT):
- Baltimore (BWI) - $266
- Boston (BOS) - $361 (non-stop)
- Los Angeles (LAX) - $404
- Portland (PDX) - $420
- Tampa (TPA) - $382 (non-stop)
- Washington Reagan (DCA) - $230
Round trips to San Juan (SJU):
- Austin (AUS) - $285 (non-stop)
- Baltimore (BWI) - $295 (non-stop)
- Boston (BOS) - $287 (non-stop)
- Los Angeles (LAX) - $310
- Newark (EWR) - $247 (non-stop)
- Portland (PDX) - $486
- Salt Lake City (SLC) - $442
- Seattle (SEA) - $484
- Washington Dulles (IAD) - $327 (non-stop)
- Washington Reagan (DCA) - $288 (non-stop)
Round trips to Santiago (STI):
- Houston (IAH) - $440
Round trips to Santo Domingo (SDQ):
- Austin (AUS) - $412
- Boston (BOS) - $365 (non-stop)
- Houston (IAH) - $464
- Las Vegas (LAS) - $427
- Los Angeles (LAX) - $472
- Miami (MIA) - $275 (non-stop)
- Newark (EWR) - $315 (non-stop)
- Orlando (MCO) - $347
- Philadelphia (PHL) - $421
- Philadelphia (PHL) - $421 (non-stop)
Round trips to Sint Maarten (SXM):
- Atlanta (ATL) - $406 (non-stop)
- Baltimore (BWI) - $314 (non-stop)
- Boston (BOS) - $450 (non-stop)
- Las Vegas (LAS) - $466
- New York (JFK) - $330 (non-stop)
- Orlando (MCO) - $485 (non-stop)
- Philadelphia (PHL) - $400 (non-stop)
- Washington Reagan (DCA) - $357
Round trips to St. John's (ANU):
- New York (JFK) - $416 (non-stop)
- Newark (EWR) - $416 (non-stop)
Round trips to Tobago (TAB):
- Fort Lauderdale (FLL) - $401
- Miami (MIA) - $391
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How to Book
We've archived the booking information because we noticed availability has changed or the fares have gone up since it was first published. The inspiration is yours to keep 🙂
