$91+ Cheap flights from the United States to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
LAX — SJU
Aug 7 — Aug 141
Round-trip
1 adult, Economy
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Find cheap flights from USA to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from USA to CaribbeanExplore the most affordable flight options available from USA to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 8, 2026.
Explore the most affordable flight options available from USA to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 8, 2026.
This Frontier deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/217:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/7![Frontier logo]()
$244
This Super.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/7![Frontier logo]()
$245
This Cheapflightsfares deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:30 am
MCO
- SJU
1 stop12h 20m
Frontier
Mon 10/129:49 pm
SJU
- MCO
Nonstop3h 08m
Frontier
Deal found 7/7![Frontier logo]()
$246
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:30 am
ORD
- SJU
1 stop9h 12m
United Airlines
Wed 8/262:20 pm
SJU
- ORD
1 stop10h 06m
United Airlines
Deal found 7/8![United Airlines logo]()
$246
This Cheapflightsfares deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:40 am
MCO
- SJU
Nonstop3h 03m
Frontier
Sat 8/18:37 pm
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 7/7![Frontier logo]()
$247
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:00 am
ORD
- SJU
1 stop12h 33m
American Airlines
Tue 9/112:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 7/8![American Airlines logo]()
$247
This Frontier deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:35 pm
MCO
- SJU
Nonstop3h 08m
Frontier
Thu 8/65:45 pm
SJU
- MCO
1 stop14h 13m
Frontier
Deal found 7/7![Frontier logo]()
$248
This Super.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$248
This Priceline deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:05 am
MCO
- SJU
Nonstop2h 53m
Frontier
Fri 11/66:31 pm
SJU
- MCO
Nonstop3h 12m
Frontier
Deal found 7/7![Frontier logo]()
$249
This Super.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$249
This Super.com deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/164:25 pm
MCO
- SJU
Nonstop3h 07m
Frontier
Sat 7/183:10 am
SJU
- MCO
Nonstop3h 00m
Frontier
Deal found 7/6![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1611:17 pm
MCO
- SJU
Nonstop2h 58m
Frontier
Fri 7/1712:21 pm
SJU
- MCO
Nonstop3h 14m
Frontier
Deal found 7/7![Frontier logo]()
$251
Best flights from USA to CaribbeanDiscover carefully curated flight deals from USA to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 8, 2026.
Discover carefully curated flight deals from USA to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 8, 2026.
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:50 am
ORD
- SJU
1 stop10h 48m
United Airlines
Fri 9/44:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Deal found 7/7![United Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:10 am
MCO
- SJU
2 stops10h 50m
Southwest
Wed 9/26:00 am
SJU
- MCO
2 stops11h 55m
Southwest
Deal found 7/7![Southwest logo]()
$268
This Delta deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:28 pm
JFK
- SJU
Nonstop4h 24m
Delta
Thu 8/205:50 pm
SJU
- JFK
Nonstop4h 14m
Delta
Deal found 7/4![Delta logo]()
$287
This JetBlue deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:00 pm
JFK
- SJU
Nonstop3h 57m
JetBlue
Mon 8/313:24 pm
SJU
- JFK
Nonstop3h 58m
JetBlue
Deal found 7/7![JetBlue logo]()
$297
This Copa Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:32 pm
JFK
- PUJ
1 stop26h 04m
Copa Airlines
Sun 9/275:41 am
PUJ
- JFK
1 stop19h 19m
Copa Airlines
Deal found 7/5![Copa Airlines logo]()
$530
This Arajet deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:00 pm
EWR
- PUJ
Nonstop4h 19m
Arajet
Sat 8/297:10 pm
PUJ
- EWR
Nonstop4h 20m
Arajet
Deal found 7/7![Arajet logo]()
$577
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:00 am
ORD
- SJU
1 stop7h 45m
United Airlines
Thu 8/202:20 pm
SJU
- ORD
1 stop10h 06m
United Airlines
Deal found 7/3![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:28 pm
JFK
- SJU
Nonstop4h 24m
Delta
Thu 8/205:50 pm
SJU
- JFK
Nonstop4h 14m
Delta
Deal found 7/4![Delta logo]()
$297
This Arajet deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:59 am
EWR
- PUJ
1 stop9h 51m
Multiple Airlines
Thu 8/202:05 am
PUJ
- EWR
1 stop8h 25m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$607
This JetBlue deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:59 pm
JFK
- SJU
1 stop8h 59m
JetBlue
Tue 9/87:50 pm
SJU
- JFK
Nonstop3h 59m
JetBlue
Deal found 7/5![JetBlue logo]()
$309
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/39:05 pm
MCO
- SJU
Nonstop3h 05m
Southwest
Thu 8/65:30 am
SJU
- MCO
2 stops12h 20m
Southwest
Deal found 7/7![Southwest logo]()
$313
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:11 am
LGA
- SJU
1 stop10h 27m
United Airlines
Sun 9/67:00 am
SJU
- LGA
1 stop12h 25m
United Airlines
Deal found 7/3![United Airlines logo]()
$292
This JetBlue deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:30 pm
JFK
- SJU
Nonstop4h 02m
JetBlue
Tue 9/229:30 am
SJU
- JFK
1 stop8h 42m
JetBlue
Deal found 7/7![JetBlue logo]()
$309
This Delta deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:40 am
ORD
- SJU
1 stop8h 58m
Delta
Sat 8/295:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Deal found 7/5![Delta logo]()
$311
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
LGA
- SJU
1 stop6h 54m
United Airlines
Thu 8/207:00 am
SJU
- LGA
1 stop12h 25m
United Airlines
Deal found 7/7![United Airlines logo]()
$306
This JetBlue deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:00 pm
JFK
- SJU
Nonstop3h 56m
JetBlue
Wed 9/239:30 am
SJU
- JFK
1 stop8h 42m
JetBlue
Deal found 7/3![JetBlue logo]()
$309
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:45 pm
MCO
- SJU
1 stop10h 05m
Southwest
Wed 9/96:00 am
SJU
- MCO
2 stops13h 20m
Southwest
Deal found 7/5![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:00 am
JFK
- SJU
Nonstop4h 08m
Delta
Sat 9/55:50 pm
SJU
- JFK
Nonstop4h 14m
Delta
Deal found 7/4![Delta logo]()
$322
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:45 pm
EWR
- SJU
Nonstop4h 05m
United Airlines
Fri 7/241:00 am
SJU
- EWR
Nonstop4h 10m
United Airlines
Deal found 7/7![United Airlines logo]()
$307
This Southwest deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:45 pm
MCO
- SJU
2 stops10h 05m
Southwest
Thu 8/276:00 am
SJU
- MCO
2 stops12h 50m
Southwest
Deal found 7/4![Southwest logo]()
$346
This JetBlue deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:30 pm
JFK
- SJU
Nonstop4h 02m
JetBlue
Mon 9/216:00 am
SJU
- JFK
Nonstop3h 52m
JetBlue
Deal found 7/3![JetBlue logo]()
$321
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:30 am
ORD
- SJU
1 stop8h 12m
United Airlines
Sun 9/61:00 am
SJU
- ORD
1 stop9h 13m
United Airlines
Deal found 7/7![United Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:10 am
MCO
- SJU
2 stops11h 05m
Southwest
Mon 8/246:00 am
SJU
- MCO
2 stops10h 45m
Southwest
Deal found 7/3![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:40 pm
JFK
- SJU
Nonstop3h 53m
Delta
Mon 9/77:30 am
SJU
- JFK
Nonstop3h 55m
Delta
Deal found 7/6![Delta logo]()
$357
This JetBlue deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:00 am
EWR
- SJU
Nonstop4h 08m
JetBlue
Tue 9/224:30 pm
SJU
- EWR
1 stop6h 36m
JetBlue
Deal found 7/7![JetBlue logo]()
$325
This Southwest deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:45 am
MCO
- SJU
2 stops10h 15m
Southwest
Sun 9/273:15 pm
SJU
- MCO
1 stop7h 40m
Southwest
Deal found 7/5![Southwest logo]()
$346
This JetBlue deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:35 pm
JFK
- SJU
Nonstop4h 10m
JetBlue
Wed 7/297:25 am
SJU
- JFK
Nonstop3h 56m
JetBlue
Deal found 7/7![JetBlue logo]()
$327
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Wed 10/73:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 7/7![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:23 am
ORD
- SJU
1 stop10h 06m
Delta
Sun 9/67:30 am
SJU
- ORD
1 stop10h 36m
Delta
Deal found 7/4![Delta logo]()
$366
This Copa Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:10 am
JFK
- SDQ
1 stop9h 03m
Copa Airlines
Sun 9/1312:42 pm
SDQ
- JFK
1 stop12h 18m
Copa Airlines
Deal found 7/7![Copa Airlines logo]()
$538
Last-minute flights from USA to CaribbeanDiscover last-minute flight deals from USA to Caribbean. Data last updated July 8, 2026 and is based on user searches.
Discover last-minute flight deals from USA to Caribbean. Data last updated July 8, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 7/137:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/7![Frontier logo]()
$245
This Frontier deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/217:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/7![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:15 am
MCO
- SJU
Nonstop3h 01m
Frontier
Wed 7/223:10 am
SJU
- MCO
Nonstop3h 00m
Frontier
Deal found 7/7![Frontier logo]()
$246
This Super.com deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/144:35 pm
MCO
- SJU
Nonstop3h 07m
Frontier
Fri 7/178:37 pm
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 7/6![Frontier logo]()
$249
This Super.com deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/164:25 pm
MCO
- SJU
Nonstop3h 07m
Frontier
Sat 7/183:10 am
SJU
- MCO
Nonstop3h 00m
Frontier
Deal found 7/6![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1611:17 pm
MCO
- SJU
Nonstop2h 58m
Frontier
Fri 7/1712:21 pm
SJU
- MCO
Nonstop3h 14m
Frontier
Deal found 7/7![Frontier logo]()
$251
This Cheapflightsfares deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:40 am
MCO
- SJU
Nonstop3h 03m
Frontier
Sat 8/18:37 pm
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 7/7![Frontier logo]()
$247
This Frontier deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:35 pm
MCO
- SJU
Nonstop3h 08m
Frontier
Thu 8/65:45 pm
SJU
- MCO
1 stop14h 13m
Frontier
Deal found 7/7![Frontier logo]()
$248
This Super.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$248
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:00 am
ORD
- SJU
1 stop12h 33m
American Airlines
Tue 9/112:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 7/8![American Airlines logo]()
$247
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:30 am
ORD
- SJU
1 stop9h 12m
United Airlines
Wed 8/262:20 pm
SJU
- ORD
1 stop10h 06m
United Airlines
Deal found 7/8![United Airlines logo]()
$246
This Super.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$249
One-way flights from USA to CaribbeanSearch for one-way flight options from USA to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 8, 2026.
Search for one-way flight options from USA to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 8, 2026.
This Booking.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:00 pm
EWR
- AUA
1 stop7h 30m
Arajet
Deal found 7/5![Arajet logo]()
$91
This Booking.com deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:00 pm
EWR
- AUA
1 stop7h 30m
Arajet
Deal found 7/6![Arajet logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:59 am
EWR
- AUA
1 stop9h 16m
Arajet
Deal found 7/8![Arajet logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1411:17 pm
MCO
- SJU
Nonstop2h 58m
Frontier
Deal found 7/8![Frontier logo]()
$126
This American Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:30 am
ORD
- SJU
1 stop15h 29m
American Airlines
Deal found 7/7![American Airlines logo]()
$126
This eDestinos deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:38 am
MCO
- SJU
1 stop14h 45m
Frontier
Deal found 7/4![Frontier logo]()
$127
This Expedia deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:21 pm
MCO
- SJU
1 stop11h 58m
Frontier
Deal found 7/3![Frontier logo]()
$128
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:05 am
ORD
- SJU
1 stop7h 33m
Delta
Deal found 7/7![Delta logo]()
$128
This Frontier deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/195:01 am
MCO
- SJU
Nonstop2h 56m
Frontier
Deal found 7/7![Frontier logo]()
$129
This American Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:59 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 7/6![American Airlines logo]()
$129
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:00 pm
MCO
- SJU
Nonstop3h 05m
Southwest
Deal found 7/7![Southwest logo]()
$130
This Booking.com deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/5![Frontier logo]()
$130
Find flight deals from USA to Caribbean
Keep the following information in mind while searching for USA to Caribbean flight deals. Data was last updated July 8, 2026.
Round-trip from | $244 (Kiwi.com) |
|---|---|
One-way from | $91 (Booking.com) |
Popular in | May |
Cheapest in | October |
Average price | $362 |
Good round-trip deal | $198 or less |
Good one-way deal | $88 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from USA to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 8, 2026.
Use the filters below to find and compare flights from the United States to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 8/28
8:50 am-8:38 pm
1 stop10h 48m
San Juan Luis Munoz Marin Intl
Fri 9/4
4:55 pm-11:40 pm
1 stop7h 45m
$246
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Wed 8/26
11:10 am-10:00 pm
2 stops10h 50m
San Juan Luis Munoz Marin Intl
Wed 9/2
6:00 am-5:55 pm
2 stops11h 55m
$268
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Tue 8/18
7:28 pm-11:52 pm
Nonstop4h 24m
San Juan Luis Munoz Marin Intl
Thu 8/20
5:50 pm-10:04 pm
Nonstop4h 14m
$287
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 8/14
5:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Thu 8/20
2:20 pm-11:26 pm
1 stop10h 06m
$289
New YorkSan Juan
LGA - SJU
LGASJU
New York LaGuardia
Thu 8/27
10:11 am-8:38 pm
1 stop10h 27m
San Juan Luis Munoz Marin Intl
Sun 9/6
7:00 am-7:25 pm
1 stop12h 25m
$292
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Sat 8/22
1:00 pm-4:57 pm
Nonstop3h 57m
San Juan Luis Munoz Marin Intl
Mon 8/31
3:24 pm-7:22 pm
Nonstop3h 58m
$297
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Mon 8/10
7:28 pm-11:52 pm
Nonstop4h 24m
San Juan Luis Munoz Marin Intl
Thu 8/20
5:50 pm-10:04 pm
Nonstop4h 14m
$297
New YorkSan Juan
LGA - SJU
LGASJU
New York LaGuardia
Sun 8/16
6:00 am-12:54 pm
1 stop6h 54m
San Juan Luis Munoz Marin Intl
Thu 8/20
7:00 am-7:25 pm
1 stop12h 25m
$306
NewarkSan Juan
EWR - SJU
EWRSJU
Newark
Mon 7/20
7:45 pm-11:50 pm
Nonstop4h 05m
San Juan Luis Munoz Marin Intl
Fri 7/24
1:00 am-5:10 am
Nonstop4h 10m
$307
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Tue 9/1
2:59 pm-11:58 pm
1 stop8h 59m
San Juan Luis Munoz Marin Intl
Tue 9/8
7:50 pm-11:49 pm
Nonstop3h 59m
$309
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from USA to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from USA with our price prediction graph.
ORD-SJU
MCO-SJU
EWR-SJU
EWR-PUJ
JFK-SJU
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from the United States to Caribbean
US0-0CB
ORD-SJU
MCO-SJU
EWR-SJU
EWR-PUJ
What is the cheapest month to book a flight from USA to Caribbean?
Currently, September is the cheapest month in which you can book a flight from USA to Caribbean (average of $413). Flying from USA to Caribbean in December is currently the most expensive (average of $568). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from US to CB?
Find hourly flight availability from USA to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 8, 2026.
One of the essential ways to save on airfare from USA to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 22% on airfare.
How far ahead should I book a flight from USA to Caribbean?
To ensure you get the cheapest price possible for a flight from USA to Caribbean, you should look to book at least 29 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from USA to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from USA to Caribbean. Price data was last updated on July 4, 2026.
Travelers seeking maximum savings on their USA to Caribbean flight should consider departing on Monday mornings when fares are most often at their lowest. Tuesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated July 8, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from the United States to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Crew
8.5
Overall
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Overall
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Overall
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Overall
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Overall
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Overall
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from USA to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for USA to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from USA to Caribbean by cabin class
Find flights from USA to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
USA and Caribbean flights
Browse other USA and Caribbean flight options. Last updated on July 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Caribbean
Find the right flight back to USA after your stay in Caribbean
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
USA to Caribbean flights
Consider these flights traveling from USA to Caribbean.
Top 10 airlines flying from USA to Caribbean
Discover the top 10 airlines that operate flights from USA to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$85 | Average$411 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$325 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$108 | Average$572 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$112 | Average$266 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$512 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$129 | Average$712 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$154 | Average$501 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$161 | Average$623 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$162 | Average$480 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$166 | Average$582 | FlexibilityNo cancel fee | On-time69% |