Caribbean 
in $349-$424 RT
Dealbot
Does the airport situation feel like a hard no right now? …yeah, fair.
But when the endgame is crystal-clear water, zero worries, and a drink that costs less than your Uber to the airport? Suddenly the chaos feels… negotiable.
We’ve got a full charcuterie board of routes to choose from, with dates until 2027 — except DCA–SXM, the lone wolf flying via Air Canada.
A word to the wise: the peak summer dates overlap almost perfectly with rainy and hurricane season, so aim for Apr–May or Nov–Feb instead. The winter window is festive but fierce (in a good way) — Christmas crowds give way to Carnival chaos in Jan–Feb, and ticket prices rise accordingly. So, book early, or donate generously to the airline gods.
P.S. Sample itineraries are listed below to give you a running start :-)
Taking off ✈️
Tip Published: Apr 03, 2026
Round trips to Aruba (AUA):
- Salt Lake City (SLC) - $379
Round trips to Curaçao (CUR):
- San Diego (SAN) - $424
Round trips to Grand Cayman (GCM):
- Denver (DEN) - $379
Round trips to Montego Bay (MBJ):
- Las Vegas (LAS) - $392
- Phoenix (PHX) - $392
- Portland (PDX) - $392
Round trips to Nassau (NAS):
- Austin (AUS) - $351
Round trips to Providenciales (PLS):
- Phoenix (PHX) - $365
Round trips to Sint Maarten (SXM):
- Washington Reagan (DCA) - $349
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 🙂
