$106+ Cheap flights from Reagan-National (DCA) 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — SJU
Aug 5 — Aug 121
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Reagan-National 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Reagan-National to Caribbean
Cheapest
Best
Last-minute
One-way
Cheapest flights from Reagan-National to CaribbeanExplore the most affordable flight options available from Reagan-National to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 6, 2026.
Explore the most affordable flight options available from Reagan-National to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 6, 2026.
This Southwest deal was found by Cheapflights users on 7/1. 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 8/188:00 am
DCA
- SJU
2 stops10h 10m
Southwest
Tue 8/255:15 am
SJU
- DCA
1 stop10h 50m
Southwest
Deal found 7/1![Southwest logo]()
$316
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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.
Wed 8/128:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Wed 8/195:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/2![JetBlue logo]()
$319
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.
Thu 8/275:05 pm
DCA
- SJU
1 stop6h 45m
Southwest
Tue 9/11:20 pm
SJU
- DCA
2 stops9h 45m
Southwest
Deal found 7/3![Southwest logo]()
$321
This Super.com deal was found by Cheapflights users on 7/2. 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.
Fri 8/288:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Tue 9/15:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/2![JetBlue logo]()
$324
This Southwest deal was found by Cheapflights users on 7/1. 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 8/186:00 am
DCA
- SJU
1 stop6h 20m
Southwest
Sat 8/228:20 am
SJU
- DCA
1 stop7h 35m
Southwest
Deal found 7/1![Southwest logo]()
$326
This JetBlue deal was found by Cheapflights users on 7/2. 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 8/318:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Tue 9/15:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/2![JetBlue logo]()
$327
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Tue 9/15:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/3![JetBlue logo]()
$328
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.
Mon 8/178:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Tue 8/255:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/5![JetBlue logo]()
$329
This Southwest deal was found by Cheapflights users on 7/1. 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 9/56:00 am
DCA
- SJU
1 stop8h 00m
Southwest
Wed 9/91:45 pm
SJU
- DCA
2 stops9h 20m
Southwest
Deal found 7/1![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 7/2. 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 8/175:05 pm
DCA
- SJU
1 stop6h 45m
Southwest
Sat 8/226:25 am
SJU
- DCA
1 stop9h 30m
Southwest
Deal found 7/2![Southwest logo]()
$331
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Wed 8/265:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/4![JetBlue logo]()
$332
This Orbitz deal was found by Cheapflights users on 7/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:00 am
DCA
- SJU
Nonstop3h 50m
JetBlue
Thu 10/19:30 am
SJU
- DCA
2 stops13h 29m
JetBlue
Deal found 7/2![JetBlue logo]()
$333
Best flights from Reagan-National to CaribbeanDiscover carefully curated flight deals from Reagan-National to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 6, 2026.
Discover carefully curated flight deals from Reagan-National to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 6, 2026.
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.
Sun 8/166:35 pm
DCA
- SJU
1 stop5h 55m
Southwest
Fri 8/216:00 am
SJU
- DCA
1 stop12h 00m
Southwest
Deal found 7/3![Southwest logo]()
$321
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:05 pm
DCA
- SJU
2 stops12h 24m
United Airlines
Thu 8/131:00 am
SJU
- DCA
1 stop6h 49m
United Airlines
Deal found 7/5![United Airlines logo]()
$366
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/314:45 pm
DCA
- SJU
1 stop7h 09m
JetBlue
Tue 9/15:05 am
SJU
- DCA
1 stop9h 08m
JetBlue
Deal found 7/4![JetBlue logo]()
$385
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.
Wed 7/226:02 am
DCA
- SJU
1 stop10h 36m
Delta
Sat 7/257:20 am
SJU
- DCA
1 stop9h 40m
Delta
Deal found 7/5![Delta logo]()
$402
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/105:00 am
DCA
- SXM
1 stop8h 22m
American Airlines
Mon 8/174:39 pm
SXM
- DCA
1 stop16h 24m
American Airlines
Deal found 7/1![American Airlines logo]()
$467
This Southwest deal was found by Cheapflights users on 7/1. 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 11/1111:45 am
DCA
- SJU
2 stops9h 30m
Southwest
Sun 11/156:05 am
SJU
- DCA
1 stop6h 10m
Southwest
Deal found 7/1![Southwest logo]()
$364
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Sat 11/76:00 am
DCA
- SJU
1 stop6h 41m
United Airlines
Sat 11/141:00 pm
SJU
- DCA
1 stop8h 38m
United Airlines
Deal found 7/2![United Airlines logo]()
$390
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.
Mon 8/106:10 am
DCA
- NAS
1 stop9h 54m
JetBlue
Fri 8/216:27 pm
NAS
- DCA
1 stop5h 05m
JetBlue
Deal found 7/3![JetBlue logo]()
$391
This Southwest deal was found by Cheapflights users on 7/1. 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.
Fri 9/2512:15 pm
DCA
- SJU
2 stops9h 55m
Southwest
Fri 10/25:00 am
SJU
- DCA
2 stops9h 15m
Southwest
Deal found 7/1![Southwest logo]()
$364
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:30 am
DCA
- SJU
1 stop8h 14m
United Airlines
Mon 10/121:00 am
SJU
- DCA
2 stops13h 23m
United Airlines
Deal found 7/4![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 7/2. 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 11/136:05 am
DCA
- NAS
1 stop5h 30m
Delta
Tue 11/174:55 pm
NAS
- DCA
1 stop5h 20m
Delta
Deal found 7/2![Delta logo]()
$434
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.
Sun 10/256:00 am
DCA
- NAS
1 stop5h 30m
JetBlue
Fri 10/302:55 pm
NAS
- DCA
1 stop8h 39m
JetBlue
Deal found 7/5![JetBlue logo]()
$400
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Sun 8/96:16 am
DCA
- SXM
2 stops9h 23m
American Airlines
Thu 8/132:22 pm
SXM
- DCA
1 stop9h 19m
American Airlines
Deal found 7/1![American Airlines logo]()
$468
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.
Sat 11/77:00 am
DCA
- SJU
1 stop13h 15m
Southwest
Wed 11/186:15 am
SJU
- DCA
2 stops10h 05m
Southwest
Deal found 7/5![Southwest logo]()
$390
This JetBlue deal was found by Cheapflights users on 7/2. 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.
Wed 7/298:00 am
DCA
- SJU
Nonstop4h 00m
JetBlue
Wed 8/55:39 pm
SJU
- DCA
Nonstop3h 53m
JetBlue
Deal found 7/2![JetBlue logo]()
$402
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:50 pm
DCA
- SXM
1 stop17h 03m
Delta
Fri 9/183:18 pm
SXM
- DCA
1 stop8h 25m
Delta
Deal found 7/3![Delta logo]()
$451
This Southwest deal was found by Cheapflights users on 7/1. 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 8/176:00 am
DCA
- SXM
1 stop8h 05m
Southwest
Fri 8/213:05 pm
SXM
- DCA
2 stops17h 40m
Southwest
Deal found 7/1![Southwest logo]()
$395
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.
Thu 9/106:14 am
DCA
- SXM
1 stop7h 46m
JetBlue
Sat 9/193:05 pm
SXM
- DCA
1 stop8h 26m
JetBlue
Deal found 7/3![JetBlue logo]()
$411
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:40 pm
DCA
- AUA
1 stop16h 20m
Delta
Tue 9/151:55 pm
AUA
- DCA
1 stop9h 04m
Delta
Deal found 7/3![Delta logo]()
$481
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:00 am
DCA
- PUJ
1 stop8h 27m
United Airlines
Sat 9/261:50 pm
PUJ
- DCA
1 stop9h 02m
United Airlines
Deal found 7/5![United Airlines logo]()
$492
This Southwest deal was found by Cheapflights users on 7/2. 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 11/76:10 am
DCA
- SJU
2 stops8h 25m
Southwest
Sat 11/145:40 am
SJU
- DCA
2 stops11h 15m
Southwest
Deal found 7/2![Southwest logo]()
$410
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.
Sun 9/66:20 am
DCA
- SXM
1 stop7h 22m
JetBlue
Thu 9/173:05 pm
SXM
- DCA
1 stop8h 26m
JetBlue
Deal found 7/3![JetBlue logo]()
$416
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:40 pm
DCA
- AUA
1 stop16h 20m
Delta
Thu 9/171:55 pm
AUA
- DCA
1 stop9h 04m
Delta
Deal found 7/3![Delta logo]()
$481
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:00 pm
DCA
- PLS
1 stop15h 07m
American Airlines
Sun 10/41:07 pm
PLS
- DCA
1 stop10h 06m
American Airlines
Deal found 7/5![American Airlines logo]()
$595
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.
Tue 7/217:15 am
DCA
- AUA
1 stop8h 20m
United Airlines
Fri 7/241:50 pm
AUA
- DCA
1 stop9h 04m
United Airlines
Deal found 7/3![United Airlines logo]()
$498
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 9/312:15 pm
DCA
- SJU
2 stops9h 55m
Southwest
Mon 9/75:00 am
SJU
- DCA
2 stops9h 10m
Southwest
Deal found 7/4![Southwest logo]()
$414
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 9/128:00 am
DCA
- STT
1 stop6h 41m
JetBlue
Sat 9/193:40 pm
STT
- DCA
1 stop6h 06m
JetBlue
Deal found 7/3![JetBlue logo]()
$428
This Delta deal was found by Cheapflights users on 7/1. 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 7/171:30 pm
DCA
- AUA
2 stops21h 40m
Delta
Wed 7/221:55 pm
AUA
- DCA
1 stop9h 04m
Delta
Deal found 7/1![Delta logo]()
$494
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.
Sat 7/2511:50 am
DCA
- NAS
1 stop6h 40m
Southwest
Thu 7/308:45 am
NAS
- DCA
1 stop7h 10m
Southwest
Deal found 7/5![Southwest logo]()
$425
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.
Wed 9/98:00 am
DCA
- STT
1 stop6h 41m
JetBlue
Sat 9/193:40 pm
STT
- DCA
1 stop6h 06m
JetBlue
Deal found 7/3![JetBlue logo]()
$428
Last-minute flights from Reagan-National to CaribbeanDiscover last-minute flight deals from Reagan-National to Caribbean. Data last updated July 6, 2026 and is based on user searches.
Discover last-minute flight deals from Reagan-National to Caribbean. Data last updated July 6, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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.
Wed 8/128:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Wed 8/195:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/2![JetBlue logo]()
$319
This Southwest deal was found by Cheapflights users on 7/2. 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.
Fri 8/1412:55 pm
DCA
- SJU
1 stop9h 15m
Southwest
Wed 8/198:20 am
SJU
- DCA
2 stops10h 05m
Southwest
Deal found 7/2![Southwest logo]()
$330
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.
Mon 8/178:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Tue 8/255:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/5![JetBlue logo]()
$329
This Southwest deal was found by Cheapflights users on 7/2. 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 8/175:05 pm
DCA
- SJU
1 stop6h 45m
Southwest
Sat 8/226:25 am
SJU
- DCA
1 stop9h 30m
Southwest
Deal found 7/2![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 7/1. 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 8/188:00 am
DCA
- SJU
2 stops10h 10m
Southwest
Tue 8/255:15 am
SJU
- DCA
1 stop10h 50m
Southwest
Deal found 7/1![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 7/1. 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 8/186:00 am
DCA
- SJU
1 stop6h 20m
Southwest
Sat 8/228:20 am
SJU
- DCA
1 stop7h 35m
Southwest
Deal found 7/1![Southwest logo]()
$326
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Wed 8/265:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/4![JetBlue logo]()
$332
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Tue 9/15:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/3![JetBlue logo]()
$328
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.
Thu 8/275:05 pm
DCA
- SJU
1 stop6h 45m
Southwest
Tue 9/11:20 pm
SJU
- DCA
2 stops9h 45m
Southwest
Deal found 7/3![Southwest logo]()
$321
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Tue 9/15:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/5![JetBlue logo]()
$337
This Super.com deal was found by Cheapflights users on 7/2. 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.
Fri 8/288:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Tue 9/15:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/2![JetBlue logo]()
$324
This JetBlue deal was found by Cheapflights users on 7/2. 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 8/318:00 am
DCA
- SJU
Nonstop3h 59m
JetBlue
Tue 9/15:39 pm
SJU
- DCA
Nonstop3h 52m
JetBlue
Deal found 7/2![JetBlue logo]()
$327
One-way flights from Reagan-National to CaribbeanSearch for one-way flight options from Reagan-National to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
Search for one-way flight options from Reagan-National to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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.
Wed 8/57:25 am
DCA
- NAS
1 stop6h 33m
JetBlue
Deal found 7/2![JetBlue logo]()
$106
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.
Mon 8/317:50 am
DCA
- NAS
1 stop5h 52m
JetBlue
Deal found 7/3![JetBlue logo]()
$107
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:00 am
DCA
- SXM
1 stop6h 37m
JetBlue
Deal found 7/4![JetBlue logo]()
$129
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:00 am
DCA
- SXM
1 stop6h 37m
JetBlue
Deal found 7/5![JetBlue logo]()
$130
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.
Fri 8/146:00 am
DCA
- SXM
1 stop8h 05m
Southwest
Deal found 7/5![Southwest logo]()
$131
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.
Fri 7/317:25 am
DCA
- NAS
1 stop6h 21m
JetBlue
Deal found 7/5![JetBlue logo]()
$134
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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.
Sat 8/297:50 am
DCA
- MBJ
1 stop7h 32m
JetBlue
Deal found 7/2![JetBlue logo]()
$137
This Delta deal was found by Cheapflights users on 7/1. 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.
Wed 9/26:59 am
DCA
- NAS
1 stop4h 52m
Delta
Deal found 7/1![Delta logo]()
$137
This Justfly.com 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:50 am
DCA
- MBJ
1 stop7h 31m
JetBlue
Deal found 7/3![JetBlue logo]()
$138
This Air Canada deal was found by Cheapflights users on 7/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:40 pm
DCA
- NAS
2 stops24h 55m
Air Canada
Deal found 7/1![Air Canada logo]()
$140
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:40 pm
DCA
- NAS
2 stops24h 55m
Air Canada
Deal found 7/4![Air Canada logo]()
$142
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Tue 8/185:00 am
DCA
- SJU
1 stop13h 33m
American Airlines
Deal found 7/1![American Airlines logo]()
$143
Find flight deals from Reagan-National to Caribbean
Keep the following information in mind while searching for Reagan-National to Caribbean flight deals. Data was last updated July 6, 2026.
Round-trip from | $316 (Southwest) |
|---|---|
One-way from | $106 (Cheapflightsfares) |
Popular in | June |
Cheapest in | October |
Average price | $409 |
Good round-trip deal | $437 or less |
Good one-way deal | $208 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Reagan-National 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 6, 2026.
Use the filters below to find and compare flights from Washington, D.C. Reagan-National Airport to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Washington, D.C.San Juan
DCA - SJU
DCASJU
Washington, D.C. Reagan-National
Sun 8/16
6:35 pm-12:30 am
1 stop5h 55m
San Juan Luis Munoz Marin Intl
Fri 8/21
6:00 am-6:00 pm
1 stop12h 00m
$321
Washington, D.C.San Juan
DCA - SJU
DCASJU
Washington, D.C. Reagan-National
Wed 11/11
11:45 am-10:15 pm
2 stops9h 30m
San Juan Luis Munoz Marin Intl
Sun 11/15
6:05 am-11:15 am
1 stop6h 10m
$364
Washington, D.C.San Juan
DCA - SJU
DCASJU
Washington, D.C. Reagan-National
Fri 9/25
12:15 pm-10:10 pm
2 stops9h 55m
San Juan Luis Munoz Marin Intl
Fri 10/2
5:00 am-2:15 pm
2 stops9h 15m
$364
Washington, D.C.San Juan
DCA - SJU
DCASJU
Washington, D.C. Reagan-National
Mon 8/10
5:05 pm-5:29 am
2 stops12h 24m
San Juan Luis Munoz Marin Intl
Thu 8/13
1:00 am-7:49 am
1 stop6h 49m
$366
Washington, D.C.San Juan
DCA - SJU
DCASJU
Washington, D.C. Reagan-National
Mon 8/31
4:45 pm-11:54 pm
1 stop7h 09m
San Juan Luis Munoz Marin Intl
Tue 9/1
5:05 am-2:13 pm
1 stop9h 08m
$385
Washington, D.C.San Juan
DCA - SJU
DCASJU
Washington, D.C. Reagan-National
Sat 11/7
6:00 am-1:41 pm
1 stop6h 41m
San Juan Luis Munoz Marin Intl
Sat 11/14
1:00 pm-8:38 pm
1 stop8h 38m
$390
Washington, D.C.San Juan
DCA - SJU
DCASJU
Washington, D.C. Reagan-National
Fri 10/9
6:30 am-2:44 pm
1 stop8h 14m
San Juan Luis Munoz Marin Intl
Mon 10/12
1:00 am-2:23 pm
2 stops13h 23m
$390
Washington, D.C.San Juan
DCA - SJU
DCASJU
Washington, D.C. Reagan-National
Sat 11/7
7:00 am-9:15 pm
1 stop13h 15m
San Juan Luis Munoz Marin Intl
Wed 11/18
6:15 am-3:20 pm
2 stops10h 05m
$390
Washington, D.C.Nassau
DCA - NAS
DCANAS
Washington, D.C. Reagan-National
Mon 8/10
6:10 am-4:04 pm
1 stop9h 54m
Nassau Intl
Fri 8/21
6:27 pm-11:32 pm
1 stop5h 05m
$391
Washington, D.C.Simpson Bay
DCA - SXM
DCASXM
Washington, D.C. Reagan-National
Mon 8/17
6:00 am-2:05 pm
1 stop8h 05m
Simpson Bay Princess Juliana
Fri 8/21
3:05 pm-8:45 am
2 stops17h 40m
$395
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Reagan-National to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Reagan-National with our price prediction graph.
DCA-SJU
DCA-NAS
DCA-SXM
DCA-MBJ
DCA-AUA
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 Washington, D.C. Reagan-National Airport to Caribbean
DCA-0CB
DCA-SJU
DCA-NAS
DCA-SXM
DCA-MBJ
What is the cheapest month to book a flight from Washington, D.C. Reagan-National Airport to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Caribbean (average of $108). Flying from Washington, D.C. Reagan-National Airport to Caribbean in May is currently the most expensive (average of $925). 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 DCA to CB?
Find hourly flight availability from Reagan-National 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 6, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Washington, D.C. Reagan-National Airport to Caribbean as you normally would.
Weekly flight availability from Washington, D.C. Reagan-National Airport to Caribbean
Explore weekly flight availability from Reagan-National to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 6, 2026.
The most flights from DCA to 0CB are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
How far ahead should I book a flight from Washington, D.C. Reagan-National Airport to Caribbean?
The price you pay for your flight from Washington, D.C. Reagan-National Airport to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 76 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 6, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Washington, D.C. Reagan-National Airport to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Reagan-National 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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
Alternative routes for Reagan-National 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 Reagan-National to Caribbean by cabin class
Find flights from Reagan-National to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Reagan-National and Caribbean flights
Browse other Reagan-National and Caribbean flight options. Last updated on July 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Reagan-National to Caribbean flights
Consider these flights traveling from Reagan-National to Caribbean.
Top 7 airlines flying from Reagan-National to Caribbean
Discover the top 7 airlines that operate flights from Reagan-National 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 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$103 | Average$399 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$142 | Average$552 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$220 | Average$521 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$220 | Average$486 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$230 | Average$597 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$252 | Average$596 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$389 | Average$498 | FlexibilityNo cancel fee | On-time67% |