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$85+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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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 November 3, 2025.

This Trip.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/184:10 pmBDL - SJU
Nonstop3h 55mJetBlue
Fri 11/216:01 amSJU - BDL
Nonstop4h 04mJetBlue
Deal found 11/2$214
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/166:16 amBOS - SJU
1 stop10h 03mMultiple Airlines
Thu 11/2011:55 amSJU - BOS
2 stops13h 49mMultiple Airlines
Deal found 11/1$214
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:11 pmBOS - SJU
1 stop13h 22mSpirit Airlines
Thu 12/1111:38 amSJU - BOS
1 stop8h 28mSpirit Airlines
Deal found 11/2$216
This CheapOair deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:11 pmBOS - SJU
1 stop13h 22mSpirit Airlines
Mon 12/156:14 pmSJU - BOS
1 stop6h 42mSpirit Airlines
Deal found 11/2$217
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/73:18 pmBDL - SJU
Nonstop3h 56mFrontier
Mon 12/158:30 amSJU - BDL
Nonstop4h 08mFrontier
Deal found 11/1$218
This Frontier deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Sun 11/168:40 amBOS - SJU
2 stops15h 52mFrontier
Thu 11/207:11 amSJU - BOS
2 stops18h 33mFrontier
Deal found 10/31$218
This Priceline deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mMultiple Airlines
Sun 1/118:25 amSJU - BOS
Nonstop4h 23mMultiple Airlines
Deal found 10/31$220
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/97:39 pmBDL - SJU
1 stop19h 31mFrontier
Thu 11/203:12 pmSJU - BDL
Nonstop4h 05mFrontier
Deal found 11/2$221
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:34 pmBOS - SJU
Nonstop4h 07mSpirit Airlines
Fri 1/95:27 pmSJU - BOS
Nonstop4h 07mSpirit Airlines
Deal found 11/2$221
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/52:48 pmBDL - SJU
Nonstop3h 56mFrontier
Fri 12/1210:45 amSJU - BDL
Nonstop4h 08mFrontier
Deal found 11/1$222
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/812:33 pmBDL - SJU
Nonstop3h 56mFrontier
Sun 12/1411:15 amSJU - BDL
Nonstop4h 08mFrontier
Deal found 11/1$223
This Trip.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/187:40 amBOS - SJU
Nonstop4h 04mJetBlue
Mon 11/249:25 pmSJU - BOS
Nonstop4h 05mJetBlue
Deal found 11/1$223

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 November 3, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$207
(Kiwi.com)

One-way from

$69
(Priceline)

Popular in

December

Cheapest in

January

Average price

$285

Good round-trip deal

$262 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Boston Logan Intl-San Juan flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-San Juan flights.
Search Deals
From Massachusetts to Puerto Rico
Search Deals
One-way flight from Massachusetts to Puerto Rico
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Puerto Rico.
Search Deals
Price to beat on a one-way flight from Massachusetts to Puerto Rico.
Search Deals

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 November 3, 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

Thu 1/29

2:18 pm-11:56 pm

1 stop8h 38m

San Juan Luis Munoz Marin Intl

Mon 2/2

4:49 pm-1:53 pm

2 stops22h 04m

$235

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Mon 11/17

4:10 pm-9:05 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Fri 11/21

6:01 am-9:05 am

Nonstop4h 04m

$254

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 11/17

8:10 am-1:15 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Thu 12/4

2:20 pm-5:45 pm

Nonstop4h 25m

$262

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 11/15

6:00 am-9:26 pm

2 stops14h 26m

San Juan Luis Munoz Marin Intl

Tue 11/18

8:10 am-5:28 pm

1 stop10h 18m

$263

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 11/15

6:00 am-9:26 pm

2 stops14h 26m

San Juan Luis Munoz Marin Intl

Wed 11/19

5:50 pm-11:59 pm

1 stop7h 09m

$263

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 11/17

1:10 pm-11:56 pm

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Thu 11/20

2:27 pm-5:49 pm

Nonstop4h 22m

$267

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 12/8

8:10 am-1:10 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Mon 12/15

2:10 pm-10:26 pm

1 stop9h 16m

$267

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 11/15

12:10 pm-11:13 pm

1 stop10h 03m

San Juan Luis Munoz Marin Intl

Thu 12/4

2:20 pm-5:45 pm

Nonstop4h 25m

$267

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 1/19

5:45 am-1:17 pm

1 stop6h 32m

San Juan Luis Munoz Marin Intl

Thu 1/22

2:05 am-9:14 am

1 stop8h 09m

$271

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 1/24

4:05 pm-12:36 am

1 stop7h 31m

San Juan Luis Munoz Marin Intl

Mon 2/2

2:05 am-9:14 am

1 stop8h 09m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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, February is the cheapest month in which you can book a flight from Massachusetts to Puerto Rico (average of $65). Flying from Massachusetts to Puerto Rico in September is currently the most expensive (average of $147). 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 November 3, 2025.

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 in the morning, which can drop the price by up to 25% versus a flight in the evening.

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 December 16, 2024.

Travelers seeking maximum savings on their Massachusetts to Puerto Rico flight should consider departing on Thursday mornings 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.

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

    American Airlines, JetBlue, and Delta can get you from Massachusetts to Puerto Rico in just under 3h 55m. Your travel time can differ by up to 4h 43m. Massachusetts and Puerto Rico are separated by a distance of 1669 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 Frontier ($85), JetBlue ($128), and Southwest ($132).

  • 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, February is the cheapest month in which you can book a flight from Massachusetts to Puerto Rico (average of $65). Flying from Massachusetts to Puerto Rico in September is currently the most expensive (average of $147). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$59Average$255FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$99Average$524FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$270FlexibilityNo cancel feeOn-time65%
DeltaCheapest$144Average$328FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$190Average$386FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$288Average$486FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$383Average$624FlexibilityNo cancel feeOn-time63%

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