$158+ Cheap flights from Massachusetts to Puerto Rico
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Oct 28 — Nov 41
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Massachusetts 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 Massachusetts to Puerto Rico
Cheapest
Best
Last-minute
One-way
Cheapest flights from Massachusetts to Puerto RicoExplore the most affordable flight options available from Massachusetts to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 28, 2026.
Explore the most affordable flight options available from Massachusetts to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/1710:19 am -
1 stop11h 36m
Sat 12/56:25 am -
1 stop28h 16m
Deal found 9/23![Multiple Airlines logo]()
$289
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:34 am -
1 stop12h 33m
Fri 12/188:20 am -
Nonstop4h 19m
Deal found 9/28![Frontier logo]()
$296
This Super.com deal was found by Cheapflights users on 9/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1411:34 am -
1 stop12h 33m
Fri 12/188:20 am -
Nonstop4h 19m
Deal found 9/27![Frontier logo]()
$297
This Super.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 12/1111:34 am -
1 stop12h 33m
Thu 12/177:43 pm -
1 stop16h 19m
Deal found 9/25![Frontier logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 11/1512:34 pm -
1 stop23h 51m
Wed 12/26:25 am -
1 stop28h 14m
Deal found 9/27![Multiple Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/1710:19 am -
1 stop11h 36m
Wed 12/27:25 am -
1 stop27h 14m
Deal found 9/23![Multiple Airlines logo]()
$300
This CheapOair deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 12/1111:08 am -
1 stop14h 05m
Fri 12/188:20 am -
Nonstop4h 19m
Deal found 9/24![Frontier logo]()
$302
This FlightHub deal was found by Cheapflights users on 9/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1411:34 am -
1 stop12h 33m
Thu 12/177:43 pm -
1 stop16h 19m
Deal found 9/27![Frontier logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 10/1710:19 am -
1 stop11h 36m
Fri 10/237:00 am -
1 stop26h 29m
Deal found 9/26![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 11/412:39 pm -
1 stop11h 20m
Wed 11/118:45 am -
1 stop27h 59m
Deal found 9/25![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/1710:19 am -
1 stop11h 36m
Wed 12/23:43 am -
1 stop7h 28m
Deal found 9/23![Multiple Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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.
Fri 10/165:16 pm -
2 stops18h 15m
Sun 10/184:29 pm -
2 stops24h 20m
Deal found 9/25![American Airlines logo]()
$316
Best flights from Massachusetts to Puerto RicoDiscover carefully curated flight deals from Massachusetts to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 28, 2026.
Discover carefully curated flight deals from Massachusetts to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 28, 2026.
This JetBlue deal was found by Cheapflights users on 9/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:30 pm -
Nonstop4h 05m
Thu 11/265:01 am -
Nonstop4h 12m
Deal found 9/28![JetBlue logo]()
$327
This United Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:30 am -
2 stops14h 20m
Sat 10/241:05 am -
1 stop6h 38m
Deal found 9/24![United Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 12/38:35 am -
Nonstop4h 07m
Tue 12/82:53 pm -
Nonstop4h 22m
Deal found 9/25![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 12/22:25 pm -
2 stops9h 25m
Tue 12/86:10 am -
2 stops9h 20m
Deal found 9/23![Southwest logo]()
$376
This FlightHub deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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.
Wed 10/147:42 pm -
1 stop14h 00m
Sun 10/181:19 pm -
1 stop21h 01m
Deal found 9/24![Multiple Airlines logo]()
$640
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 11/146:00 am -
1 stop6h 32m
Thu 11/198:25 am -
1 stop11h 49m
Deal found 9/25![United Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 2/171:44 pm -
2 stops8h 43m
Sat 2/2011:38 am -
2 stops26h 41m
Deal found 9/24![American Airlines logo]()
$693
This CheapOair deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/2411:06 am -
1 stop26h 28m
Sun 11/293:29 pm -
1 stop19h 42m
Deal found 9/23![Frontier logo]()
$700
This JetBlue deal was found by Cheapflights users on 9/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:08 pm -
Nonstop4h 05m
Tue 11/177:00 am -
Nonstop4h 13m
Deal found 9/27![JetBlue logo]()
$367
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/245:45 am -
1 stop6h 49m
Tue 10/277:25 am -
2 stops11h 32m
Deal found 9/23![United Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/148:50 am -
Nonstop4h 02m
Tue 10/201:15 pm -
1 stop9h 53m
Deal found 9/24![Delta logo]()
$382
This Southwest deal was found by Cheapflights users on 9/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:25 pm -
2 stops9h 35m
Tue 11/176:10 am -
2 stops9h 20m
Deal found 9/27![Southwest logo]()
$398
This Delta deal was found by Cheapflights users on 9/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:50 am -
Nonstop4h 02m
Wed 10/282:02 pm -
Nonstop4h 13m
Deal found 9/26![Delta logo]()
$400
This JetBlue deal was found by Cheapflights users on 9/26. 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.
Tue 10/273:55 pm -
1 stop8h 42m
Wed 11/47:01 am -
1 stop8h 59m
Deal found 9/26![JetBlue logo]()
$408
This JetBlue deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:25 pm -
1 stop7h 12m
Tue 11/37:01 am -
1 stop8h 59m
Deal found 9/24![JetBlue logo]()
$408
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/179:23 am -
2 stops14h 27m
Fri 11/138:25 am -
2 stops14h 34m
Deal found 9/23![United Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/238:05 am -
2 stops15h 04m
Sat 10/2412:09 am -
1 stop9h 09m
Deal found 9/24![United Airlines logo]()
$452
This JetBlue deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/223:55 pm -
1 stop10h 11m
Thu 10/296:00 am -
1 stop9h 00m
Deal found 9/25![JetBlue logo]()
$476
This United Airlines deal was found by Cheapflights users on 9/26. 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.
Wed 11/117:31 am -
2 stops15h 26m
Sat 11/141:09 am -
1 stop7h 34m
Deal found 9/26![United Airlines logo]()
$452
This Priceline deal was found by Cheapflights users on 9/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:42 pm -
1 stop14h 00m
Thu 10/154:36 pm -
1 stop17h 48m
Deal found 9/26![Multiple Airlines logo]()
$687
This American Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 12/197:03 pm -
1 stop16h 09m
Wed 1/138:15 am -
1 stop8h 32m
Deal found 9/24![American Airlines logo]()
$694
This JetBlue deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/115:30 am -
1 stop7h 56m
Fri 10/166:04 am -
1 stop8h 25m
Deal found 9/25![JetBlue logo]()
$499
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:12 am -
2 stops13h 45m
Sat 10/311:09 am -
1 stop7h 34m
Deal found 9/23![United Airlines logo]()
$464
This JetBlue deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:55 pm -
1 stop10h 11m
Wed 10/2111:15 am -
1 stop10h 45m
Deal found 9/24![JetBlue logo]()
$510
This Expedia deal was found by Cheapflights users on 9/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:42 am -
1 stop7h 57m
Mon 12/77:30 am -
1 stop11h 31m
Deal found 9/28![Multiple Airlines logo]()
$757
This FlightHub deal was found by Cheapflights users on 9/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:10 am -
1 stop5h 25m
Sat 10/1710:35 am -
1 stop23h 49m
Deal found 9/27![Multiple Airlines logo]()
$782
This Priceline deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/224:44 pm -
1 stop16h 20m
Thu 10/298:00 pm -
1 stop15h 44m
Deal found 9/24![JetBlue logo]()
$589
This United deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:25 pm -
2 stops18h 14m
Sat 10/245:41 pm -
2 stops14h 02m
Deal found 9/23![Multiple Airlines logo]()
$804
This JetBlue deal was found by Cheapflights users on 9/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1911:30 am -
1 stop8h 45m
Fri 11/275:01 am -
1 stop6h 39m
Deal found 9/27![JetBlue logo]()
$596
This JetBlue deal was found by Cheapflights users on 9/26. 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.
Sat 12/124:00 pm -
1 stop8h 59m
Thu 12/176:15 am -
1 stop8h 35m
Deal found 9/26![JetBlue logo]()
$596
Last-minute flights from Massachusetts to Puerto RicoDiscover last-minute flight deals from Massachusetts to Puerto Rico. Data last updated September 28, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Puerto Rico. Data last updated September 28, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/211:36 am -
1 stop22h 38m
Wed 10/711:12 am -
1 stop23h 50m
Deal found 9/23![Frontier logo]()
$360
This Cheapflightsfares deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/211:36 am -
1 stop22h 38m
Sun 10/411:08 am -
1 stop23h 43m
Deal found 9/23![Frontier logo]()
$399
This CheapOair deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/311:26 am -
1 stop9h 22m
Fri 10/307:40 pm -
Nonstop4h 18m
Deal found 9/25![Multiple Airlines logo]()
$384
This Cheapflightsfares deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/311:26 am -
1 stop30h 17m
Fri 10/93:00 am -
1 stop8h 02m
Deal found 9/23![Frontier logo]()
$396
This Cheapflightsfares deal was found by Cheapflights users on 9/27. 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.
Sat 10/311:26 am -
1 stop9h 22m
Wed 10/76:42 pm -
1 stop16h 20m
Deal found 9/27![Frontier logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/511:36 am -
1 stop11h 37m
Fri 10/167:44 pm -
1 stop15h 18m
Deal found 9/25![Frontier logo]()
$397
This Justfly.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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.
Thu 10/1511:47 am -
1 stop22h 10m
Wed 10/2111:17 am -
1 stop23h 45m
Deal found 9/23![Frontier logo]()
$380
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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.
Fri 10/165:16 pm -
2 stops18h 15m
Sun 10/184:29 pm -
2 stops24h 20m
Deal found 9/25![American Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 9/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:16 pm -
2 stops18h 15m
Mon 10/196:30 am -
2 stops10h 19m
Deal found 9/26![American Airlines logo]()
$363
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Wed 10/215:16 pm -
2 stops16h 30m
Sun 10/2512:21 pm -
2 stops28h 28m
Deal found 9/28![American Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 9/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:16 pm -
2 stops28h 46m
Thu 10/296:20 am -
2 stops10h 29m
Deal found 9/26![American Airlines logo]()
$349
This JetBlue deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:30 am -
1 stop7h 49m
Wed 11/43:25 pm -
1 stop10h 02m
Deal found 9/25![JetBlue logo]()
$402
One-way flights from Massachusetts to Puerto RicoSearch for one-way flight options from Massachusetts to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.
Search for one-way flight options from Massachusetts to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/1710:19 am -
1 stop27h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 11/210:59 am -
1 stop27h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$159
This FlightHub deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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.
Sun 11/2211:06 am -
1 stop21h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$167
This Southwest deal was found by Cheapflights users on 9/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1611:20 am -
2 stops10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Southwest logo]()
$168
This Super.com deal was found by Cheapflights users on 9/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:00 am -
Nonstop4h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![JetBlue logo]()
$169
This Super.com deal was found by Cheapflights users on 9/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:00 pm -
1 stop6h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![JetBlue logo]()
$171
This Expedia deal was found by Cheapflights users on 9/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/911:08 am -
Nonstop4h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Frontier logo]()
$172
This Super.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/308:08 pm -
Nonstop4h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![JetBlue logo]()
$173
This JetBlue deal was found by Cheapflights users on 9/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:55 am -
1 stop7h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![JetBlue logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 11/1512:39 pm -
1 stop11h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Frontier logo]()
$175
This Priceline deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 12/411:08 am -
1 stop26h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Frontier logo]()
$194
This Priceline deal was found by Cheapflights users on 9/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2711:06 am -
1 stop14h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$204
Find flight deals from Massachusetts to Puerto Rico
Keep the following information in mind while searching for Massachusetts to Puerto Rico flight deals. Data was last updated September 28, 2026.
Round-trip from | $289 (Kiwi.com) |
|---|---|
One-way from | $158 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $323 |
Good round-trip deal | $371 or less |
Good one-way deal | $225 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts 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 7,457,451 searches. Data last updated September 28, 2026.
Use the filters below to find and compare flights from Massachusetts to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonSan Juan
BOS Boston Logan Intl - SJU San Juan Luis Munoz Marin Intl
BOSSJU
Boston Logan Intl
Tue 12/1
8:15 am-1:25 pm
Nonstop4h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$174
BostonSan Juan
BOS Boston Logan Intl - SJU San Juan Luis Munoz Marin Intl
BOSSJU
Boston Logan Intl
Tue 11/3
8:08 pm-1:13 am
Nonstop4h 05m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$174
Quickest round-trip
BostonSan Juan
BOS Boston Logan Intl - SJU San Juan Luis Munoz Marin Intl
BOSSJU
Boston Logan Intl
Mon 10/26
10:15 am-2:19 pm
Nonstop4h 04m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$174
BostonSan Juan
BOS Boston Logan Intl - SJU San Juan Luis Munoz Marin Intl
BOSSJU
Boston Logan Intl
Tue 12/1
9:10 am-4:54 pm
1 stop6h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
BostonSan Juan
BOS Boston Logan Intl - SJU San Juan Luis Munoz Marin Intl
BOSSJU
Boston Logan Intl
Sun 11/15
6:05 am-4:56 pm
1 stop9h 51m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
BostonSan Juan
BOS Boston Logan Intl - SJU San Juan Luis Munoz Marin Intl
BOSSJU
Boston Logan Intl
Wed 10/21
9:30 am-8:35 pm
2 stops11h 05m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$199
BostonSan Juan
BOS Boston Logan Intl - SJU San Juan Luis Munoz Marin Intl
BOSSJU
Boston Logan Intl
Mon 1/11
6:00 am-2:40 pm
1 stop7h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
BostonSan Juan
BOS Boston Logan Intl - SJU San Juan Luis Munoz Marin Intl
BOSSJU
Boston Logan Intl
Sat 1/9
4:54 pm-6:15 am
2 stops12h 21m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
BostonSan Juan
BOS Boston Logan Intl - SJU San Juan Luis Munoz Marin Intl
BOSSJU
Boston Logan Intl
Tue 1/12
9:12 am-10:22 pm
2 stops12h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
BostonSan Juan
BOS Boston Logan Intl - SJU San Juan Luis Munoz Marin Intl
BOSSJU
Boston Logan Intl
Wed 1/20
9:12 am-9:00 pm
1 stop10h 48m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$209
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Massachusetts with our price prediction graph.
BOS-SJU
BOS-PSE
ORH-SJU
BOS-VQS
BOS-BQN
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 Massachusetts to Puerto Rico
USMA-PR0
BOS-SJU
BOS-PSE
ORH-SJU
BOS-VQS
What is the cheapest month to book a flight from Massachusetts to Puerto Rico?
Currently, January is the cheapest month in which you can book a flight from Massachusetts to Puerto Rico (average of $282). Flying from Massachusetts to Puerto Rico in July is currently the most expensive (average of $462). 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 MA to PR?
Find hourly flight availability from Massachusetts to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 28, 2026.
When flying from Massachusetts to Puerto Rico, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 14% versus a flight in the morning.
Weekly flight availability from Massachusetts to Puerto Rico
Explore weekly flight availability from Massachusetts to Puerto Rico. 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 September 28, 2026.
The most flights from USMA to PR0 are scheduled on a Sunday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).
How far ahead should I book a flight from Massachusetts to Puerto Rico?
Booking 46 days in advance of your planned departure date is, on average, the best time to get cheap flights from Massachusetts to Puerto Rico. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Massachusetts to Puerto Rico?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Puerto Rico. Price data was last updated on September 26, 2026.
Travelers seeking maximum savings on their Massachusetts to Puerto Rico flight should consider departing on Tuesday at noon when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Puerto Rico. 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
Return Flight Options
Top destinations
Alternative routes for Massachusetts 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 Massachusetts to Puerto Rico by cabin class
Find flights from Massachusetts to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Massachusetts and Puerto Rico flights
Browse other Massachusetts and Puerto Rico flight options. Last updated on September 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Puerto Rico
Find the right flight back to Massachusetts after your stay in Puerto Rico
Massachusetts to Puerto Rico flights
Consider these flights traveling from Massachusetts to Puerto Rico.
Top 6 airlines flying from Massachusetts to Puerto Rico
Discover the top 6 airlines that operate flights from Massachusetts 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 7,457,451 searches. Data last updated September 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$89 | Average$297 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$163 | Average$397 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$546 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$212 | Average$394 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$259 | Average$459 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$313 | Average$541 | FlexibilityNo cancel fee | On-time63% |