$68+ Cheap flights from Chesapeake, VA to Puerto Rico
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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Mar 21 — Mar 281
1 adult, Economy
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Find cheap flights from Chesapeake to Puerto Rico 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 Chesapeake to Puerto Rico
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Cheapest flights from Chesapeake to Puerto RicoExplore the most affordable flight options available from Chesapeake to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 19, 2026.
Explore the most affordable flight options available from Chesapeake to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 19, 2026.
This Delta deal was found by Cheapflights users on 2/16. 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 4/147:00 am
ORF
- SJU
1 stop6h 25m
Delta
Tue 4/216:15 am
SJU
- ORF
1 stop6h 42m
Delta
Deal found 2/16![Delta logo]()
$206
This CheapOair deal was found by Cheapflights users on 2/18. 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 4/131:50 pm
ORF
- SJU
Nonstop3h 30m
Multiple Airlines
Sat 4/188:00 am
SJU
- ORF
1 stop9h 49m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$208
This Priceline deal was found by Cheapflights users on 2/15. 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.
Thu 3/266:43 pm
ORF
- SJU
1 stop7h 15m
Multiple Airlines
Sun 3/298:15 am
SJU
- ORF
Nonstop3h 41m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$209
This CheapOair deal was found by Cheapflights users on 2/19. 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 4/238:41 pm
ORF
- SJU
1 stop26h 07m
Frontier
Wed 4/293:21 am
SJU
- ORF
1 stop16h 25m
Frontier
Deal found 2/19![Frontier logo]()
$210
This CheapOair deal was found by Cheapflights users on 2/16. 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 5/106:43 pm
ORF
- SJU
1 stop7h 18m
Multiple Airlines
Mon 5/189:00 am
SJU
- ORF
Nonstop3h 41m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$212
This Priceline deal was found by Cheapflights users on 2/17. 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 4/276:43 pm
ORF
- SJU
1 stop7h 18m
Frontier
Sat 5/28:00 am
SJU
- ORF
1 stop9h 49m
Frontier
Deal found 2/17![Frontier logo]()
$213
This American Airlines deal was found by Cheapflights users on 2/16. 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 stop16h 52m
American Airlines
Tue 4/146:00 am
SJU
- ORF
1 stop11h 00m
American Airlines
Deal found 2/16![American Airlines logo]()
$215
This Frontier deal was found by Cheapflights users on 2/15. 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 3/233:26 pm
ORF
- BQN
1 stop10h 16m
Frontier
Tue 3/312:43 am
BQN
- ORF
1 stop12h 00m
Frontier
Deal found 2/15![Frontier logo]()
$216
This CheapOair deal was found by Cheapflights users on 2/18. 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 5/76:43 pm
ORF
- SJU
1 stop7h 18m
Multiple Airlines
Mon 5/119:00 am
SJU
- ORF
Nonstop3h 41m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$217
This KAYAK deal was found by Cheapflights users on 2/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2310:04 am
ORF
- SJU
1 stop7h 47m
JetBlue
Wed 4/19:00 am
SJU
- ORF
Nonstop3h 41m
JetBlue
Deal found 2/15![JetBlue logo]()
$222
This United Airlines deal was found by Cheapflights users on 2/17. 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 4/276:00 am
ORF
- SJU
1 stop8h 44m
United Airlines
Fri 5/11:00 am
SJU
- ORF
2 stops8h 31m
United Airlines
Deal found 2/17![United Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 2/18. 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 4/207:03 am
ORF
- SJU
1 stop9h 28m
Delta
Fri 4/242:45 pm
SJU
- ORF
1 stop7h 48m
Delta
Deal found 2/18![Delta logo]()
$226
Best flights from Chesapeake to Puerto RicoDiscover carefully curated flight deals from Chesapeake to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 19, 2026.
Discover carefully curated flight deals from Chesapeake to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 19, 2026.
This Delta deal was found by Cheapflights users on 2/15. 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 4/182:03 pm
ORF
- SJU
1 stop6h 21m
Delta
Wed 4/225:34 pm
SJU
- ORF
1 stop7h 03m
Delta
Deal found 2/15![Delta logo]()
$206
This United Airlines deal was found by Cheapflights users on 2/17. 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 4/276:00 am
ORF
- SJU
1 stop8h 44m
United Airlines
Thu 4/301:00 am
SJU
- ORF
2 stops8h 31m
United Airlines
Deal found 2/17![United Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 2/17. 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 4/17:41 pm
ORF
- SJU
1 stop13h 19m
American Airlines
Wed 4/154:30 pm
SJU
- ORF
1 stop7h 29m
American Airlines
Deal found 2/17![American Airlines logo]()
$235
This Frontier deal was found by Cheapflights users on 2/15. 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 3/266:43 pm
ORF
- BQN
1 stop6h 59m
Frontier
Thu 4/22:43 am
BQN
- ORF
1 stop12h 20m
Frontier
Deal found 2/15![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Wed 3/256:45 am
ORF
- BQN
1 stop18h 57m
Multiple Airlines
Thu 4/22:43 am
BQN
- ORF
1 stop12h 20m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 2/18. 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 4/275:50 am
ORF
- SJU
1 stop10h 33m
Delta
Wed 5/67:15 am
SJU
- ORF
1 stop10h 02m
Delta
Deal found 2/18![Delta logo]()
$226
This United Airlines deal was found by Cheapflights users on 2/18. 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 5/28:00 am
ORF
- SJU
2 stops15h 50m
United Airlines
Wed 5/64:55 pm
SJU
- ORF
1 stop6h 55m
United Airlines
Deal found 2/18![United Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 2/18. 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.
Sun 4/267:03 am
ORF
- SJU
1 stop9h 28m
Delta
Wed 5/67:15 am
SJU
- ORF
1 stop10h 02m
Delta
Deal found 2/18![Delta logo]()
$226
This Delta deal was found by Cheapflights users on 2/17. 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 3/315:50 am
ORF
- SJU
1 stop5h 56m
Delta
Tue 4/77:30 am
SJU
- ORF
1 stop8h 38m
Delta
Deal found 2/17![Delta logo]()
$226
This Frontier deal was found by Cheapflights users on 2/18. 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 3/233:26 pm
ORF
- BQN
1 stop10h 16m
Frontier
Tue 3/312:43 am
BQN
- ORF
1 stop12h 00m
Frontier
Deal found 2/18![Frontier logo]()
$278
This Delta deal was found by Cheapflights users on 2/18. 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 4/285:45 am
ORF
- SJU
1 stop7h 07m
Delta
Wed 5/67:15 am
SJU
- ORF
1 stop10h 02m
Delta
Deal found 2/18![Delta logo]()
$226
This Priceline deal was found by Cheapflights users on 2/16. 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.
Thu 3/57:13 pm
ORF
- BQN
1 stop6h 44m
Frontier
Thu 3/123:02 am
BQN
- ORF
1 stop8h 45m
Frontier
Deal found 2/16![Frontier logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 3/26:45 am
ORF
- BQN
1 stop19h 12m
Multiple Airlines
Thu 3/53:42 am
BQN
- ORF
1 stop11h 49m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 2/18. 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.
Sun 5/37:03 am
ORF
- SJU
1 stop9h 28m
Delta
Wed 5/67:15 am
SJU
- ORF
1 stop10h 02m
Delta
Deal found 2/18![Delta logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 3/2711:33 am
ORF
- BQN
2 stops38h 24m
Frontier
Tue 3/312:43 am
BQN
- ORF
1 stop12h 00m
Frontier
Deal found 2/15![Frontier logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Tue 3/246:45 am
ORF
- BQN
1 stop18h 57m
Multiple Airlines
Mon 3/302:42 am
BQN
- ORF
1 stop19h 05m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 2/18. 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.
Sun 5/37:03 am
ORF
- SJU
1 stop9h 28m
Delta
Thu 5/76:15 am
SJU
- ORF
1 stop6h 43m
Delta
Deal found 2/18![Delta logo]()
$226
This Priceline deal was found by Cheapflights users on 2/16. 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.
Fri 3/63:26 pm
ORF
- BQN
1 stop10h 36m
Multiple Airlines
Sun 3/159:15 pm
BQN
- ORF
1 stop11h 59m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$330
This Delta deal was found by Cheapflights users on 2/18. 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 4/297:03 am
ORF
- SJU
1 stop9h 28m
Delta
Wed 5/67:15 am
SJU
- ORF
1 stop10h 02m
Delta
Deal found 2/18![Delta logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 3/2212:35 pm
ORF
- BQN
1 stop13h 22m
Frontier
Tue 3/312:43 am
BQN
- ORF
1 stop12h 00m
Frontier
Deal found 2/15![Frontier logo]()
$304
This Frontier deal was found by Cheapflights users on 2/16. 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.
Fri 3/63:26 pm
ORF
- BQN
1 stop10h 36m
Frontier
Fri 3/133:03 am
BQN
- ORF
1 stop11h 28m
Frontier
Deal found 2/16![Frontier logo]()
$306
This Delta deal was found by Cheapflights users on 2/16. 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 4/297:03 am
ORF
- SJU
1 stop9h 28m
Delta
Sat 5/25:34 pm
SJU
- ORF
1 stop7h 03m
Delta
Deal found 2/16![Delta logo]()
$231
This Expedia deal was found by Cheapflights users on 2/18. 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.
Fri 3/2010:04 am
ORF
- VQS
2 stops9h 24m
JetBlue
Fri 3/277:49 pm
VQS
- ORF
2 stops20h 13m
JetBlue
Deal found 2/18![JetBlue logo]()
$1,204
This United Airlines deal was found by Cheapflights users on 2/15. 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 4/196:04 am
ORF
- CPX
2 stops10h 09m
United Airlines
Thu 4/2310:30 am
CPX
- ORF
2 stops35h 53m
United Airlines
Deal found 2/15![United Airlines logo]()
$2,153
This United Airlines deal was found by Cheapflights users on 2/15. 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 5/56:15 am
ORF
- VQS
2 stops9h 38m
United Airlines
Thu 5/711:44 am
VQS
- ORF
3 stops12h 06m
United Airlines
Deal found 2/15![United Airlines logo]()
$5,476
Last-minute flights from Chesapeake to Puerto RicoDiscover last-minute flight deals from Chesapeake to Puerto Rico. Data last updated February 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Puerto Rico. Data last updated February 19, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 2/16. 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
Mon 3/23:53 am
SJU
- ORF
1 stop9h 12m
Frontier
Deal found 2/16![Frontier logo]()
$213
This Priceline deal was found by Cheapflights users on 2/15. 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.
Tue 2/241:02 pm
ORF
- SJU
1 stop12h 51m
Frontier
Mon 3/25:25 pm
SJU
- ORF
1 stop19h 40m
Frontier
Deal found 2/15![Frontier logo]()
$234
This Delta deal was found by Cheapflights users on 2/15. 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 3/1712:30 pm
ORF
- SJU
1 stop11h 29m
Delta
Wed 3/257:00 am
SJU
- ORF
1 stop10h 19m
Delta
Deal found 2/15![Delta logo]()
$206
This CheapOair deal was found by Cheapflights users on 2/17. 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 3/178:41 pm
ORF
- SJU
1 stop27h 17m
Spirit Airlines
Tue 3/247:54 pm
SJU
- ORF
1 stop23h 52m
Spirit Airlines
Deal found 2/17![Spirit Airlines logo]()
$233
This CheapOair deal was found by Cheapflights users on 2/16. 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 3/216:45 am
ORF
- SJU
1 stop15h 14m
Multiple Airlines
Sun 3/298:15 am
SJU
- ORF
Nonstop3h 41m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$226
This Frontier deal was found by Cheapflights users on 2/15. 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 3/213:26 pm
ORF
- BQN
1 stop10h 31m
Frontier
Tue 3/312:43 am
BQN
- ORF
1 stop12h 00m
Frontier
Deal found 2/15![Frontier logo]()
$234
This Delta deal was found by Cheapflights users on 2/15. 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.
Sun 3/2212:30 pm
ORF
- SJU
1 stop11h 29m
Delta
Wed 3/257:00 am
SJU
- ORF
1 stop10h 19m
Delta
Deal found 2/15![Delta logo]()
$231
This Frontier deal was found by Cheapflights users on 2/15. 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 3/233:26 pm
ORF
- BQN
1 stop10h 16m
Frontier
Tue 3/312:43 am
BQN
- ORF
1 stop12h 00m
Frontier
Deal found 2/15![Frontier logo]()
$216
This KAYAK deal was found by Cheapflights users on 2/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2310:04 am
ORF
- SJU
1 stop7h 47m
JetBlue
Mon 3/308:15 am
SJU
- ORF
Nonstop3h 41m
JetBlue
Deal found 2/15![JetBlue logo]()
$222
This CheapOair deal was found by Cheapflights users on 2/18. 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 3/238:41 pm
ORF
- SJU
1 stop15h 08m
Spirit Airlines
Wed 3/257:54 pm
SJU
- ORF
1 stop23h 52m
Spirit Airlines
Deal found 2/18![Spirit Airlines logo]()
$236
This Priceline deal was found by Cheapflights users on 2/15. 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.
Thu 3/266:43 pm
ORF
- SJU
1 stop7h 15m
Multiple Airlines
Sun 3/298:15 am
SJU
- ORF
Nonstop3h 41m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 2/15. 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 stop16h 52m
American Airlines
Tue 4/77:11 am
SJU
- ORF
1 stop16h 48m
American Airlines
Deal found 2/15![American Airlines logo]()
$215
One-way flights from Chesapeake to Puerto RicoSearch for one-way flight options from Chesapeake to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated February 19, 2026.
Search for one-way flight options from Chesapeake to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated February 19, 2026.
This SmartFares deal was found by Cheapflights users on 2/15. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/101:50 pm
ORF
- SJU
Nonstop3h 30m
JetBlue
Deal found 2/15![JetBlue logo]()
$68
This American Airlines deal was found by Cheapflights users on 2/16. 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 4/157:52 pm
ORF
- SJU
1 stop13h 21m
American Airlines
Deal found 2/16![American Airlines logo]()
$73
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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.
Mon 4/131:50 pm
ORF
- SJU
Nonstop3h 30m
JetBlue
Deal found 2/19![JetBlue logo]()
$74
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Thu 4/167:52 pm
ORF
- SJU
1 stop13h 21m
American Airlines
Deal found 2/17![American Airlines logo]()
$83
This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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 5/171:50 pm
ORF
- SJU
Nonstop3h 30m
JetBlue
Deal found 2/18![JetBlue logo]()
$84
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/137:52 pm
ORF
- SJU
1 stop16h 37m
American Airlines
Deal found 2/19![American Airlines logo]()
$85
This KAYAK deal was found by Cheapflights users on 2/16. 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 KAYAK 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
JetBlue
Deal found 2/16![JetBlue logo]()
$89
This American Airlines deal was found by Cheapflights users on 2/18. 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 3/103:22 pm
ORF
- SJU
1 stop14h 06m
American Airlines
Deal found 2/18![American Airlines logo]()
$93
This Frontier deal was found by Cheapflights users on 2/19. 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.
Fri 4/176:12 pm
ORF
- SJU
1 stop7h 49m
Frontier
Deal found 2/19![Frontier logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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 4/171:50 pm
ORF
- SJU
Nonstop3h 30m
JetBlue
Deal found 2/18![JetBlue logo]()
$98
This KAYAK deal was found by Cheapflights users on 2/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/151:50 pm
ORF
- SJU
Nonstop3h 30m
JetBlue
Deal found 2/19![JetBlue logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Thu 3/266:45 am
ORF
- BQN
1 stop18h 57m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$107
Find flight deals from Chesapeake to Puerto Rico
Keep the following information in mind while searching for Chesapeake to Puerto Rico flight deals. Data was last updated February 19, 2026.
Round-trip from | $206 (Delta) |
|---|---|
One-way from | $68 (SmartFares) |
Popular in | December |
Cheapest in | September |
Average price | $378 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chesapeake to Puerto Rico 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 February 19, 2026.
Use the filters below to find and compare flights from Chesapeake to Puerto Rico that are best for you.
Fly from
Chesapeake
Fly to
Puerto Rico
Route
Depart
Return
Price
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Sat 4/18
2:03 pm-8:24 pm
1 stop6h 21m
San Juan Luis Munoz Marin Intl
Wed 4/22
5:34 pm-12:37 am
1 stop7h 03m
$206
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Mon 4/27
6:00 am-2:44 pm
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Thu 4/30
1:00 am-9:31 am
2 stops8h 31m
$224
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Mon 4/27
5:50 am-4:23 pm
1 stop10h 33m
San Juan Luis Munoz Marin Intl
Wed 5/6
7:15 am-5:17 pm
1 stop10h 02m
$226
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Sun 4/26
7:03 am-4:31 pm
1 stop9h 28m
San Juan Luis Munoz Marin Intl
Wed 5/6
7:15 am-5:17 pm
1 stop10h 02m
$226
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Tue 3/31
5:50 am-11:46 am
1 stop5h 56m
San Juan Luis Munoz Marin Intl
Tue 4/7
7:30 am-4:08 pm
1 stop8h 38m
$226
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Tue 4/28
5:45 am-12:52 pm
1 stop7h 07m
San Juan Luis Munoz Marin Intl
Wed 5/6
7:15 am-5:17 pm
1 stop10h 02m
$226
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Sun 5/3
7:03 am-4:31 pm
1 stop9h 28m
San Juan Luis Munoz Marin Intl
Wed 5/6
7:15 am-5:17 pm
1 stop10h 02m
$226
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Sun 5/3
7:03 am-4:31 pm
1 stop9h 28m
San Juan Luis Munoz Marin Intl
Thu 5/7
6:15 am-12:58 pm
1 stop6h 43m
$226
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Wed 4/29
7:03 am-4:31 pm
1 stop9h 28m
San Juan Luis Munoz Marin Intl
Wed 5/6
7:15 am-5:17 pm
1 stop10h 02m
$226
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Wed 4/29
7:03 am-4:31 pm
1 stop9h 28m
San Juan Luis Munoz Marin Intl
Sat 5/2
5:34 pm-12:37 am
1 stop7h 03m
$231
Showing 1-10 of 43 results
Best time to book a flight from Chesapeake to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Chesapeake with our price prediction graph.
ORF-SJU
ORF-BQN
ORF-VQS
ORF-CPX
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 Puerto Rico
C6E-PR0
ORF-SJU
ORF-BQN
ORF-VQS
ORF-CPX
What is the cheapest month to book a flight from Chesapeake to Puerto Rico?
Currently, July is the cheapest month in which you can book a flight from Chesapeake to Puerto Rico (average of $119). Flying from Chesapeake to Puerto Rico in December is currently the most expensive (average of $259). 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 Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated February 19, 2026.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chesapeake to Puerto Rico have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
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 Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chesapeake to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chesapeake to Puerto Rico by cabin class
Find flights from Chesapeake to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chesapeake and Puerto Rico flights
Browse other Chesapeake and Puerto Rico flight options. Last updated on February 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chesapeake to Puerto Rico flights
Consider these flights traveling from Chesapeake to Puerto Rico.
Top 7 airlines flying from Chesapeake to Puerto Rico
Discover the top 7 airlines that operate flights from Chesapeake to Puerto Rico. 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 February 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$94 | Average$326 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$110 | Average$289 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$162 | Average$373 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$191 | Average$483 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$202 | Average$442 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$205 | Average$485 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$212 | Average$521 | FlexibilityNo cancel fee | On-time71% |