Puerto Rico

$99+ Cheap flights from Massachusetts 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Oct 15 — Oct 221
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Cheap 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 15, 2025.

Round-trip from

$176
(CheapOair)

One-way from

$99
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$255

Good round-trip deal

$282 or less

Good one-way deal

$136 or less
From Massachusetts to Puerto Rico
One-way flight from Massachusetts to Puerto Rico
Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Average for round-trip flights in September 2025
Price to beat on a round-trip flight from Massachusetts to Puerto Rico.
Price to beat on a one-way flight from Massachusetts to Puerto Rico.

Find flight deals from Massachusetts to Puerto Rico

Cheapest flights from Massachusetts to Puerto Rico
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 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/12:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
Sat 2/75:27 pmSJU - BOS
Nonstop4h 07mSpirit Airlines
Deal found 9/15$195
This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/22:53 pmBOS - SJU
1 stop10h 01mSpirit Airlines
Tue 10/72:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/13$202
This Cheapflightsfares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
Mon 10/62:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/14$206
This eDestinos deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:49 pmBOS - SJU
1 stop16h 15mSpirit Airlines
Tue 9/306:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/13$212
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/176:00 amBOS - SJU
1 stop9h 23mSpirit Airlines
Wed 11/1912:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/13$213
This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/12:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
Thu 11/612:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/13$214
This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 11/76:00 amBOS - SJU
1 stop9h 23mSpirit Airlines
Wed 11/1212:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/13$215
This Priceline deal was found by Cheapflights users on 9/15. 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.
Sat 11/12:15 pmBOS - SJU
1 stop10h 39mSpirit Airlines
Fri 11/712:10 pmSJU - BOS
1 stop10h 58mSpirit Airlines
Deal found 9/15$217
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 12/411:13 amBOS - SJU
1 stop7h 08mSpirit Airlines
Sat 12/66:00 amSJU - BOS
1 stop18h 25mSpirit Airlines
Deal found 9/12$218
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2712:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
Sat 10/46:44 amSJU - BOS
1 stop7h 04mSpirit Airlines
Deal found 9/15$219
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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 12/66:00 amBOS - SJU
1 stop9h 23mMultiple Airlines
Sat 12/133:59 pmSJU - BOS
1 stop9h 45mMultiple Airlines
Deal found 9/14$223
This Cheapflightsfares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:20 pmBOS - SJU
1 stop8h 36mSpirit Airlines
Tue 10/72:49 amSJU - BOS
1 stop10h 31mSpirit Airlines
Deal found 9/14$226

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 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Massachusetts to Puerto Rico that are best for you.

Fly from

Massachusetts

Fly to

Puerto Rico

Route

Depart

Return

Price

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sun 10/19

4:17 pm-11:59 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Wed 10/29

5:30 am-3:50 pm

1 stop10h 20m

$231

AlbanySan Juan

ALB - SJU

ALBSJU

Albany Intl

Tue 10/21

7:00 am-10:10 pm

2 stops15h 10m

San Juan Luis Munoz Marin Intl

Fri 10/31

7:00 pm-11:48 am

2 stops16h 48m

$235

WorcesterSan Juan

ORH - SJU

ORHSJU

Worcester

Sat 10/25

4:05 pm-11:05 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Tue 10/28

5:00 pm-3:50 pm

2 stops22h 50m

$235

HartfordPonce

BDL - PSE

BDLPSE

Hartford Bradley Intl

Sun 9/28

8:37 pm-9:30 am

1 stop12h 53m

Ponce Mercedita

Fri 10/3

10:15 am-7:57 pm

1 stop9h 42m

$258

HartfordPonce

BDL - PSE

BDLPSE

Hartford Bradley Intl

Sun 11/2

1:36 pm-11:20 am

1 stop20h 44m

Ponce Mercedita

Sat 11/8

12:15 pm-12:41 pm

1 stop25h 26m

$258

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Tue 10/21

6:00 am-2:44 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Wed 10/29

4:50 pm-11:59 pm

1 stop7h 09m

$263

HartfordAguadilla

BDL - BQN

BDLBQN

Hartford Bradley Intl

Sun 12/7

8:39 pm-11:02 am

1 stop13h 23m

Aguadilla Borinquen

Sun 12/14

11:57 am-7:40 pm

1 stop8h 43m

$264

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 10/19

5:20 pm-9:10 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sun 10/26

6:01 am-10:04 am

Nonstop4h 03m

$274

BostonAguadilla

BOS - BQN

BOSBQN

Boston Logan Intl

Sat 10/25

4:12 pm-7:25 am

1 stop15h 13m

Aguadilla Borinquen

Sat 11/1

8:15 am-11:11 pm

1 stop14h 56m

$275

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 2/7

7:00 pm-11:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Sat 3/7

7:00 am-10:10 am

Nonstop4h 10m

$280

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 results
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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.
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

What is the cheapest month to book a flight from Massachusetts to Puerto Rico?

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Puerto Rico (average of $254). Flying from Massachusetts to Puerto Rico in June is currently the most expensive (average of $339). 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 15, 2025.

When flying from Massachusetts to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 15, 2025.

The most flights from USMA to PR0 are scheduled on a Friday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).

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.
  • How long is the flight from Massachusetts to Puerto Rico?

    American Airlines, Frontier, and United Airlines can get you from Massachusetts to Puerto Rico in just under 7h 42m. Your travel time can differ by up to 5h 11m. Massachusetts and Puerto Rico are separated by a distance of 1681 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Massachusetts to Puerto Rico one-way?

    The cheapest airlines for a one-way flight from Massachusetts to Puerto Rico are American Airlines ($113), JetBlue ($128), and Frontier ($129).

  • Can I find deals for flights from Massachusetts to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Puerto Rico?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Puerto Rico.

  • Can I find deals for business class flights from Massachusetts to Puerto Rico?

    Yes. Cheapflights offers flight deals from Massachusetts to Puerto Rico by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Massachusetts to Puerto Rico?

    Currently, September is the cheapest month in which you can book a flight from Massachusetts to Puerto Rico (average of $254). Flying from Massachusetts to Puerto Rico in June is currently the most expensive (average of $339). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Massachusetts to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.

Top 7 airlines flying from Massachusetts to Puerto Rico

Discover the top 7 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 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$234FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$99Average$270FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$136Average$552FlexibilityNo cancel feeOn-time62%
DeltaCheapest$142Average$331FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$194Average$448FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$491FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$398Average$640FlexibilityNo cancel feeOn-time63%

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