$74+ Cheap flights from Chesapeake, VA 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Mar 1 — Mar 81
1 adult, Economy
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Find cheap flights from Chesapeake 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 Chesapeake to CaribbeanExplore the most affordable flight options available from Chesapeake to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 30, 2026.
Explore the most affordable flight options available from Chesapeake to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 30, 2026.
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:45 am
ORF
- STT
1 stop6h 46m
Spirit Airlines
Thu 3/53:36 pm
STT
- ORF
1 stop7h 14m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$190
This CheapOair deal was found by Cheapflights users on 1/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:31 pm
ORF
- STT
1 stop20h 03m
Spirit Airlines
Wed 3/45:40 pm
STT
- ORF
1 stop25h 46m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$200
This FlightHub deal was found by Cheapflights users on 1/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:45 am
ORF
- STT
1 stop6h 46m
Spirit Airlines
Sat 2/213:36 pm
STT
- ORF
1 stop7h 14m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$201
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:31 pm
ORF
- STT
1 stop20h 03m
Spirit Airlines
Tue 2/245:40 pm
STT
- ORF
1 stop25h 46m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/79:10 pm
ORF
- SJU
1 stop26h 58m
Multiple Airlines
Wed 2/114:40 pm
SJU
- ORF
2 stops19h 11m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$209
This Priceline deal was found by Cheapflights users on 1/29. 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.
Sun 4/121:50 pm
ORF
- SJU
Nonstop3h 30m
Multiple Airlines
Sat 4/1811:07 am
SJU
- ORF
1 stop6h 42m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$211
This Frontier deal was found by Cheapflights users on 1/28. 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.
Sat 5/26:43 pm
ORF
- SJU
1 stop7h 18m
Frontier
Mon 5/46:30 am
SJU
- ORF
1 stop11h 19m
Frontier
Deal found 1/28![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sun 2/811:45 am
ORF
- SJU
1 stop26h 27m
Multiple Airlines
Thu 2/124:36 pm
SJU
- ORF
1 stop26h 50m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$213
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:49 am
ORF
- SJU
1 stop14h 54m
Frontier
Fri 2/273:53 am
SJU
- ORF
1 stop12h 59m
Frontier
Deal found 1/27![Frontier logo]()
$214
This Orbitz deal was found by Cheapflights users on 1/29. 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.
Thu 2/266:45 am
ORF
- SJU
1 stop15h 24m
Multiple Airlines
Fri 3/63:58 am
SJU
- ORF
1 stop11h 33m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Fri 2/611:43 am
ORF
- SJU
1 stop21h 56m
Multiple Airlines
Tue 2/106:00 am
SJU
- ORF
1 stop7h 05m
Multiple Airlines
Deal found 1/26![Multiple Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/146:45 am
ORF
- SJU
1 stop15h 24m
Multiple Airlines
Fri 2/202:54 am
SJU
- ORF
2 stops17h 55m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$217
Best flights from Chesapeake to CaribbeanDiscover carefully curated flight deals from Chesapeake to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 30, 2026.
Discover carefully curated flight deals from Chesapeake to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 30, 2026.
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:45 am
ORF
- STT
1 stop6h 46m
Spirit Airlines
Thu 3/53:36 pm
STT
- ORF
1 stop7h 14m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/2311:39 am
ORF
- STT
2 stops27h 55m
Multiple Airlines
Mon 3/25:40 pm
STT
- ORF
1 stop25h 46m
Multiple Airlines
Deal found 1/26![Multiple Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 1/27. 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 2/173:30 pm
ORF
- SJU
1 stop7h 28m
Delta
Tue 2/246:37 pm
SJU
- ORF
1 stop6h 37m
Delta
Deal found 1/27![Delta logo]()
$226
This United Airlines deal was found by Cheapflights users on 1/27. 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 3/310:15 am
ORF
- SJU
1 stop9h 45m
United Airlines
Tue 3/107:05 am
SJU
- ORF
2 stops14h 09m
United Airlines
Deal found 1/27![United Airlines logo]()
$231
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2112:29 pm
ORF
- PUJ
2 stops26h 46m
Frontier
Sat 2/284:52 pm
PUJ
- ORF
1 stop18h 45m
Frontier
Deal found 1/28![Frontier logo]()
$312
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/17:41 pm
ORF
- NAS
1 stop15h 17m
American Airlines
Sat 3/74:36 pm
NAS
- ORF
1 stop14h 47m
American Airlines
Deal found 1/27![American Airlines logo]()
$320
This CheapOair deal was found by Cheapflights users on 1/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:31 pm
ORF
- STT
1 stop20h 03m
Spirit Airlines
Wed 3/45:40 pm
STT
- ORF
1 stop25h 46m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$200
This CheapOair deal was found by Cheapflights users on 1/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:31 pm
ORF
- STT
1 stop20h 03m
Spirit Airlines
Tue 2/245:40 pm
STT
- ORF
1 stop25h 46m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$201
This United Airlines deal was found by Cheapflights users on 1/29. 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 3/26:00 am
ORF
- SJU
2 stops14h 00m
United Airlines
Thu 3/51:35 pm
SJU
- ORF
2 stops11h 11m
United Airlines
Deal found 1/29![United Airlines logo]()
$247
This Cheapflightsfares deal was found by Cheapflights users on 1/29. 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 2/146:45 am
ORF
- STT
1 stop6h 46m
Spirit Airlines
Sat 2/213:36 pm
STT
- ORF
1 stop7h 14m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 1/29. 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 3/105:13 pm
ORF
- SJU
1 stop6h 02m
Delta
Fri 3/132:07 pm
SJU
- ORF
1 stop10h 17m
Delta
Deal found 1/29![Delta logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 2/276:45 am
ORF
- SJU
1 stop15h 24m
Multiple Airlines
Tue 3/34:11 pm
SJU
- ORF
2 stops27h 15m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$273
This Southwest deal was found by Cheapflights users on 1/29. 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 7/206:00 am
ORF
- AUA
1 stop6h 45m
Southwest
Fri 7/243:45 pm
AUA
- ORF
1 stop7h 50m
Southwest
Deal found 1/29![Southwest logo]()
$557
This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:24 pm
ORF
- STT
1 stop19h 10m
Spirit Airlines
Wed 4/294:40 pm
STT
- ORF
1 stop26h 49m
Spirit Airlines
Deal found 1/26![Spirit Airlines logo]()
$215
This United Airlines deal was found by Cheapflights users on 1/26. 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 2/236:25 am
ORF
- SJU
1 stop8h 15m
United Airlines
Wed 2/252:05 am
SJU
- ORF
2 stops13h 17m
United Airlines
Deal found 1/26![United Airlines logo]()
$278
This American Airlines deal was found by Cheapflights users on 1/27. 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 4/115:53 am
ORF
- NAS
1 stop7h 32m
American Airlines
Fri 4/173:46 pm
NAS
- ORF
1 stop8h 13m
American Airlines
Deal found 1/27![American Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Fri 2/207:31 pm
ORF
- PUJ
1 stop20h 05m
Multiple Airlines
Sat 2/284:52 pm
PUJ
- ORF
1 stop18h 45m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$300
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:31 pm
ORF
- STT
2 stops18h 00m
Spirit Airlines
Fri 2/275:40 pm
STT
- ORF
1 stop27h 09m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$229
This United Airlines deal was found by Cheapflights users on 1/28. 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 4/206:08 am
ORF
- SJU
2 stops14h 26m
United Airlines
Fri 4/247:00 am
SJU
- ORF
2 stops16h 40m
United Airlines
Deal found 1/28![United Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 1/28. 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.
Thu 2/195:40 am
ORF
- NAS
1 stop6h 46m
Delta
Wed 2/252:59 pm
NAS
- ORF
1 stop7h 24m
Delta
Deal found 1/28![Delta logo]()
$312
This United Airlines deal was found by Cheapflights users on 1/26. 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 2/284:55 pm
ORF
- SJU
2 stops12h 16m
United Airlines
Tue 3/32:05 am
SJU
- ORF
2 stops13h 17m
United Airlines
Deal found 1/26![United Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/216:45 am
ORF
- PUJ
2 stops32h 30m
Multiple Airlines
Sat 2/284:52 pm
PUJ
- ORF
1 stop18h 45m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 1/27. 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 3/36:00 am
ORF
- NAS
1 stop9h 13m
Delta
Tue 3/101:18 pm
NAS
- ORF
1 stop7h 04m
Delta
Deal found 1/27![Delta logo]()
$320
This CheapOair deal was found by Cheapflights users on 1/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:31 pm
ORF
- STT
2 stops18h 00m
Spirit Airlines
Tue 3/104:40 pm
STT
- ORF
2 stops29h 10m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/146:45 am
ORF
- MBJ
2 stops29h 17m
Multiple Airlines
Sat 2/2110:40 am
MBJ
- ORF
1 stop23h 57m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 1/27. 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 3/205:50 am
ORF
- NAS
1 stop10h 55m
Delta
Mon 3/236:10 pm
NAS
- ORF
1 stop6h 13m
Delta
Deal found 1/27![Delta logo]()
$320
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/107:33 pm
ORF
- STT
1 stop20h 04m
Spirit Airlines
Tue 2/175:40 pm
STT
- ORF
2 stops29h 10m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 1/28. 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 3/106:15 am
ORF
- PUJ
2 stops9h 03m
American Airlines
Tue 3/1712:00 pm
PUJ
- ORF
2 stops10h 53m
American Airlines
Deal found 1/28![American Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 1/27. 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.
Thu 4/235:50 am
ORF
- NAS
1 stop10h 43m
Delta
Mon 4/273:28 pm
NAS
- ORF
1 stop9h 09m
Delta
Deal found 1/27![Delta logo]()
$320
This United Airlines deal was found by Cheapflights users on 1/27. 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 4/176:00 am
ORF
- NAS
1 stop8h 57m
United Airlines
Sat 4/251:15 pm
NAS
- ORF
1 stop10h 25m
United Airlines
Deal found 1/27![United Airlines logo]()
$322
Last-minute flights from Chesapeake to CaribbeanDiscover last-minute flight deals from Chesapeake to Caribbean. Data last updated January 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Caribbean. Data last updated January 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Fri 2/611:43 am
ORF
- SJU
1 stop21h 56m
Multiple Airlines
Tue 2/106:00 am
SJU
- ORF
1 stop7h 05m
Multiple Airlines
Deal found 1/26![Multiple Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/79:10 pm
ORF
- SJU
1 stop26h 58m
Multiple Airlines
Wed 2/114:40 pm
SJU
- ORF
2 stops19h 11m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sun 2/811:45 am
ORF
- SJU
1 stop26h 27m
Multiple Airlines
Thu 2/124:36 pm
SJU
- ORF
1 stop26h 50m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$213
This FlightHub deal was found by Cheapflights users on 1/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:45 am
ORF
- STT
1 stop6h 46m
Spirit Airlines
Sat 2/213:36 pm
STT
- ORF
1 stop7h 14m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/146:45 am
ORF
- SJU
1 stop15h 24m
Multiple Airlines
Fri 2/202:54 am
SJU
- ORF
2 stops17h 55m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$217
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:31 pm
ORF
- STT
1 stop20h 03m
Spirit Airlines
Tue 2/245:40 pm
STT
- ORF
1 stop25h 46m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/216:45 am
ORF
- SJU
1 stop15h 24m
Spirit Airlines
Tue 2/243:18 pm
SJU
- ORF
2 stops28h 08m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$219
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:49 am
ORF
- SJU
1 stop14h 54m
Frontier
Fri 2/273:53 am
SJU
- ORF
1 stop12h 59m
Frontier
Deal found 1/27![Frontier logo]()
$214
This CheapOair deal was found by Cheapflights users on 1/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:31 pm
ORF
- STT
1 stop20h 03m
Spirit Airlines
Wed 3/45:40 pm
STT
- ORF
1 stop25h 46m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$200
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:45 am
ORF
- STT
1 stop6h 46m
Spirit Airlines
Thu 3/53:36 pm
STT
- ORF
1 stop7h 14m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$190
This Orbitz deal was found by Cheapflights users on 1/29. 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.
Thu 2/266:45 am
ORF
- SJU
1 stop15h 24m
Multiple Airlines
Wed 3/43:53 am
SJU
- ORF
1 stop15h 35m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$212
This Orbitz deal was found by Cheapflights users on 1/29. 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.
Thu 2/266:45 am
ORF
- SJU
1 stop15h 24m
Multiple Airlines
Fri 3/63:58 am
SJU
- ORF
1 stop11h 33m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$215
One-way flights from Chesapeake to CaribbeanSearch for one-way flight options from Chesapeake to Caribbean. Find affordable one-way fares based on user searches. Data last updated January 30, 2026.
Search for one-way flight options from Chesapeake to Caribbean. Find affordable one-way fares based on user searches. Data last updated January 30, 2026.
This American Airlines deal was found by Cheapflights users on 1/29. 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 2/227:41 pm
ORF
- SJU
1 stop13h 19m
American Airlines
Deal found 1/29![American Airlines logo]()
$74
This Frontier deal was found by Cheapflights users on 1/28. 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.
Tue 2/241:02 pm
ORF
- SJU
1 stop12h 51m
Frontier
Deal found 1/28![Frontier logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 4/258:24 pm
ORF
- SJU
1 stop16h 09m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$88
This Frontier deal was found by Cheapflights users on 1/27. 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.
Sat 2/284:37 pm
ORF
- SJU
1 stop7h 06m
Frontier
Deal found 1/27![Frontier logo]()
$91
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/237:57 pm
ORF
- SJU
1 stop15h 58m
American Airlines
Deal found 1/27![American Airlines logo]()
$94
This American Airlines deal was found by Cheapflights users on 1/28. 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 3/316:06 am
ORF
- SJU
1 stop14h 44m
American Airlines
Deal found 1/28![American Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/2311:39 am
ORF
- SJU
2 stops26h 52m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$98
This JetBlue deal was found by Cheapflights users on 1/26. 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 4/271:50 pm
ORF
- SJU
Nonstop3h 30m
JetBlue
Deal found 1/26![JetBlue logo]()
$100
This Delta deal was found by Cheapflights users on 1/28. 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 2/2512:37 pm
ORF
- SJU
1 stop7h 35m
Delta
Deal found 1/28![Delta logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/79:10 pm
ORF
- SJU
1 stop26h 58m
Frontier
Deal found 1/26![Frontier logo]()
$104
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:24 pm
ORF
- STT
1 stop19h 10m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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.
Fri 4/176:05 am
ORF
- STT
1 stop7h 26m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$136
Find flight deals from Chesapeake to Caribbean
Keep the following information in mind while searching for Chesapeake to Caribbean flight deals. Data was last updated January 30, 2026.
Round-trip from | $190 (Travelocity) |
|---|---|
One-way from | $74 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $375 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chesapeake 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 January 30, 2026.
Use the filters below to find and compare flights from Chesapeake to Caribbean that are best for you.
Fly from
Chesapeake
Fly to
Caribbean
Route
Depart
Return
Price
NorfolkSaint Thomas Island
ORF - STT
ORFSTT
Norfolk
Thu 2/26
6:45 am-2:31 pm
1 stop6h 46m
Saint Thomas Island Cyril E King
Thu 3/5
3:36 pm-9:50 pm
1 stop7h 14m
$190
NorfolkSaint Thomas Island
ORF - STT
ORFSTT
Norfolk
Wed 2/25
7:31 pm-4:34 pm
1 stop20h 03m
Saint Thomas Island Cyril E King
Wed 3/4
5:40 pm-6:26 pm
1 stop25h 46m
$200
NorfolkSaint Thomas Island
ORF - STT
ORFSTT
Norfolk
Thu 2/19
7:31 pm-4:34 pm
1 stop20h 03m
Saint Thomas Island Cyril E King
Tue 2/24
5:40 pm-6:26 pm
1 stop25h 46m
$201
NorfolkSaint Thomas Island
ORF - STT
ORFSTT
Norfolk
Mon 2/23
11:39 am-4:34 pm
2 stops27h 55m
Saint Thomas Island Cyril E King
Mon 3/2
5:40 pm-6:26 pm
1 stop25h 46m
$209
NorfolkSaint Thomas Island
ORF - STT
ORFSTT
Norfolk
Sat 2/14
6:45 am-2:31 pm
1 stop6h 46m
Saint Thomas Island Cyril E King
Sat 2/21
3:36 pm-9:50 pm
1 stop7h 14m
$209
NorfolkSaint Thomas Island
ORF - STT
ORFSTT
Norfolk
Mon 4/20
8:24 pm-3:34 pm
1 stop19h 10m
Saint Thomas Island Cyril E King
Wed 4/29
4:40 pm-7:29 pm
1 stop26h 49m
$215
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Tue 2/17
3:30 pm-11:58 pm
1 stop7h 28m
San Juan Luis Munoz Marin Intl
Tue 2/24
6:37 pm-12:14 am
1 stop6h 37m
$226
NorfolkSaint Thomas Island
ORF - STT
ORFSTT
Norfolk
Sun 2/22
7:31 pm-2:31 pm
2 stops18h 00m
Saint Thomas Island Cyril E King
Fri 2/27
5:40 pm-7:49 pm
1 stop27h 09m
$229
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Tue 3/3
10:15 am-9:00 pm
1 stop9h 45m
San Juan Luis Munoz Marin Intl
Tue 3/10
7:05 am-9:14 pm
2 stops14h 09m
$231
NorfolkSaint Thomas Island
ORF - STT
ORFSTT
Norfolk
Fri 3/6
7:31 pm-2:31 pm
2 stops18h 00m
Saint Thomas Island Cyril E King
Tue 3/10
4:40 pm-9:50 pm
2 stops29h 10m
$241
Showing 1-10 of 60 results
Best time to book a flight from Chesapeake to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Chesapeake with our price prediction graph.
ORF-SJU
ORF-STT
ORF-PUJ
ORF-SXM
ORF-NAS
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 Chesapeake to Caribbean
C6E-0CB
ORF-SJU
ORF-STT
ORF-PUJ
ORF-SXM
What is the cheapest month to book a flight from Chesapeake to Caribbean?
Currently, May is the cheapest month in which you can book a flight from Chesapeake to Caribbean (average of $113). Flying from Chesapeake to Caribbean in June is currently the most expensive (average of $212). 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.
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 January 30, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Chesapeake to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chesapeake 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 for Chesapeake to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Chesapeake to Caribbean
Discover the top 7 airlines that operate flights from Chesapeake 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 January 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$85 | Average$265 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$90 | Average$390 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$146 | Average$536 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$204 | Average$543 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$575 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$225 | Average$590 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$245 | Average$648 | FlexibilityNo cancel fee | On-time63% |