JFKSJU · San Juan
Delta · 1 stop · Economy · Aug 4 – Sep 29
$235$320good
- 27% below typical
Comfortably under the typical fare to San Juan, on dates people actually want.
See this deal →✓ Jul 10, 6:23 AM ET
When to book flights to Caribbean & Mexico
Fly in September and October and the median fare runs $320 — about 40% less than December’s $530. Computed from fares our system has observed on real NYC–Caribbean & Mexico routes, not survey guesses.
View as table
| Month | Median round-trip | Cheapest quarter from | Fares observed |
|---|---|---|---|
| January | $485 | $385 | 216 |
| February | $505 | $395 | 224 |
| March | $485 | $395 | 112 |
| April | $430 | $345 | 387 |
| May | $370 | $305 | 401 |
| June | $355 | $290 | 207 |
| July | $380 | $300 | 367 |
| August | $365 | $290 | 310 |
| September · cheapest | $320 | $260 | 64 |
| October · cheapest | $325 | $265 | 95 |
| November | $405 | $320 | 322 |
| December | $530 | $445 | 79 |
Cheapest monthsSep · Oct
Book ahead30–90 days
Peak — avoid if flexibleDec · Feb
Aggregates updated Jul 10, 12:23 PM ET.
Live Caribbean & Mexico deals right now
All deals →
JFKCUN · Cancún
American · Nonstop · Economy · Aug 6 – Oct 5
$255$420unfare
- 39% below typical
- nonstop
The cheapest we've ever logged Cancún from New York. Fares like this rarely survive the weekend.
See this deal →✓ Jul 10, 4:23 AM ET
JFKCUN · Cancún
Delta · Nonstop · Economy · Aug 17 – Oct 20
$304$420steal
- 28% below typical
- nonstop
A genuinely rare number for Cancún, and the dates include weekends.
See this deal →✓ Jul 10, 11:23 AM ET
JFKMBJ · Montego Bay
Delta · Nonstop · Economy · Sep 22 – Oct 18
$338$440good
- 25% below typical
- nonstop
Not a record, but a dependable fare on the best routing to Montego Bay.
See this deal →✓ Jul 10, 5:23 AM ET
JFKMBJ · Montego Bay
Delta · Nonstop · Economy · Aug 26 – Oct 22
- 17% below typical
- nonstop
Comfortably under the typical fare to Montego Bay, on dates people actually want.
See this deal →✓ Jul 10, 6:23 AM ET
EWRAUA · Oranjestad
United · Nonstop · Economy · Sep 25 – Oct 26
- 22% below typical
- nonstop
- staff pick
Comfortably under the typical fare to Oranjestad, on dates people actually want.
See this deal →✓ Jul 10, 3:23 AM ET
Free membership · unlocks every fare on the site
Fly to Caribbean & Mexico for less
The weekly Top 20 catches the fares that beat these medians by 30% or more — free, every Tuesday.