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Find cheap flights from Massachusetts to Puerto Rico from $49

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Massachusetts to Puerto Rico departing on 6/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
sáb 6/15
sáb 6/22

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Good to know

Low season

October

High season

July

Cheapest flight

$49
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Boston to San Juan Airport

FAQs for booking flights from Massachusetts to Puerto Rico

  • How does KAYAK find such low prices on flights from Massachusetts to Puerto Rico?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Massachusetts to Puerto Rico.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Massachusetts to Puerto Rico?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Puerto Rico from Massachusetts is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Massachusetts to Puerto Rico?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Puerto Rico with an airline and back to Massachusetts with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Massachusetts to Puerto Rico?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Puerto Rico from Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 3 airlines serving from Massachusetts to Puerto Rico

 
Need help choosing which airline to fly with from Massachusetts to Puerto Rico? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
9.0
Cape AirOverall score based on 54 reviews
8.4Comfort
8.8Boarding
9.4Crew
9.1Entertainment
8.8Food
Airline reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10.0 ExcellentSonia, Apr 2023CPX - SJU
Read more about Cape Air reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Pros: "ground crew, pilot, flight was smooth and gate connections to Jet Blue in Boston were fantastic!"
Cons: "leg room"
Pros: "The pilot was kind and to the point."
Cons: "The guy who boarded us told me to wait as his computer could not check me in. 10min later he is rushing me to get on the runway. It was 30min before scheduled take off. I had ordered food and had to cancel my order before the café had finished, so he wasted food and did not get paid and I was hurried and boarded the plane hungry. I probably won't use Cape Air again unless it's an emergency situation"
Cons: "Boarded half hour late. No explanation. Pretty standard on Cape Air these days"

I had back trouble prior to my flight and everyone was great about helping me.

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Always delays from Boston to Salt lake but this time was very long. Don’t understand while they board the passengers and then make them sit in the plane

The boarding and flight were ok, but there were several painful issues. The flight was 3:20 in the air and almost four hours door to door, but they only had snack packs on the plane. They really need to have food on longer flights or make it clear to everyone that they won’t have food. They also advertise free WiFi, but it did not work for 90% of this flight. Again, almost four hours door to door. If I had known I was flying spirit for JetBlue prices then I would have planned differently.

Service for food to our seat was a bit slow. Snack choices were just pretzels or baked chips. My seat cushion was not attached. Other than Barbie, video choice were not very good or current.

After we landed, we were held on the plane for 30 minutes. There was no one at the gate once we landed and we forced to sit on a plan that had already over an hour delayed.

almost 4 hour delay as they over booked and had to wait for 8-10 volunteers to agree to travel next day.

Old plane. No outlets for laptop or phone. Seats worn out. Area around seat dirty.

I loved the flight and the crew. It was comfortable and smooth.

The crew was openly hostile and condescending to the customers. They spent the majority of that time in the rear talking and seemed really agitated when people asked questions. I heard five different people told that the information they requested was in the handout or safety brief.

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Pros: "Nothing!!! Horrible airline with horrible staff members."
Cons: "Everything. The staff and crew of Intercaribbean airlines are very unprofessional and not helpful at all. On top of the flight delays all the luggage for that particular flight was left in Kingston. Everybody was rather nonchalant and unapologetic about the situation. I was told I would get the the following day. The next day only two of my three bags showed up. I was not compensated for the inconvenience and was told point blank that they will only deliver one of my bags to my address even though they were the reason I had NONE of my luggage in the first place. They are disgusting!!! I would never recommend this airline to anyone."
Pros: "Nice people"
Cons: "A long walk to the D3 gate, but there were no amenities there I.e. snacks (to be fair a new terminal is under construction)"
Cons: "There was no air. I understand when you are on the ground it can be limited but even after getting to altitude there was no air conditioning."
Cons: "The flight was delayed for over three hours, apparently it is a regular occurence."
Pros: "almost nothing"
Cons: "The plane had a problem that forced us to turn around right after take off and as of this writing we still don’t know what’s going on or how long we are stuck here. Planes are old and apparently maintenance could be better."
Cons: "Was a bit difficult understanding the flight attendant, she had a thick Spanish accent"

Book cheap flights from Massachusetts to Puerto Rico

Recent round-trip flight deals

6/4ter
nonstopSpirit Airlines
4h 06mBOS-SJU
6/6qui
nonstopSpirit Airlines
4h 14mSJU-BOS
$90
6/4ter
nonstop
4h 06mBOS-SJU
6/11ter
nonstop
4h 08mSJU-BOS
$98
6/4ter
nonstopFrontier
4h 12mBOS-SJU
6/11ter
nonstopFrontier
4h 08mSJU-BOS
$109
9/10ter
nonstopFrontier
4h 05mBOS-SJU
9/24ter
nonstopFrontier
4h 08mSJU-BOS
$115
6/18ter
nonstopJetBlue
4h 05mBOS-SJU
6/25ter
nonstopJetBlue
4h 04mSJU-BOS
$213
7/17qua
nonstopJetBlue
4h 04mBOS-SJU
8/15qui
nonstopJetBlue
4h 04mSJU-BOS
$248
8/8qui
1 stopAmerican Airlines
7h 52mBDL-SJU
8/11dom
1 stopAmerican Airlines
16h 39mSJU-BDL
$265
10/26sáb
1 stopAmerican Airlines
14h 59mBDL-SJU
11/2sáb
2 stopsAmerican Airlines
11h 32mSJU-BDL
$293
9/7sáb
1 stopUnited Airlines
6h 50mALB-SJU
9/10ter
1 stopUnited Airlines
9h 20mSJU-ALB
$322
9/4qua
1 stopUnited Airlines
8h 17mALB-SJU
9/16seg
1 stopUnited Airlines
9h 20mSJU-ALB
$362

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Recent one-way flight deals

6/11ter
nonstopFrontier
4h 00mBOS-SJU
$49
7/16ter
nonstopSpirit Airlines
4h 14mBOS-SJU
$53
7/17qua
nonstopJetBlue
4h 04mBOS-SJU
$112
8/13ter
1 stopAmerican Airlines
8h 37mBOS-SJU
$116
8/13ter
1 stopJetBlue
8h 20mMVY-SJU
$126
5/26dom
1 stopAmerican Airlines
11h 26mBDL-SJU
$133
6/3seg
1 stopDelta
8h 19mBDL-SJU
$162
5/29qua
nonstopDelta
4h 02mBOS-SJU
$162
5/26dom
2 stopsUnited Airlines
14h 28mBDL-SJU
$192
10/22ter
2 stopsUnited Airlines
15h 09mBOS-BQN
$207

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Last minute flights from Massachusetts to Puerto Rico

Last minute flight, train and bus deals

5/20seg
multi-stopFrontier
11h 00mBOS-SJU
6/4ter
nonstopFrontier
4h 21mSJU-BOS
$188
5/20seg
nonstop
4h 06mBOS-SJU
6/4ter
nonstop
4h 21mSJU-BOS
$189
5/20seg
nonstopSpirit Airlines
4h 06mBOS-SJU
5/29qua
nonstopSpirit Airlines
4h 24mSJU-BOS
$235
5/18sáb
nonstopSpirit Airlines
4h 06mBOS-SJU
5/29qua
multi-stopSpirit Airlines
17h 15mSJU-BOS
$239
5/19dom
nonstopJetBlue
4h 04mBDL-SJU
5/22qua
nonstopJetBlue
4h 06mSJU-BDL
$312
5/18sáb
nonstopJetBlue
3h 59mBOS-SJU
5/22qua
nonstopJetBlue
4h 14mSJU-BOS
$343
5/18sáb
multi-stopAmerican Airlines
9h 35mBOS-SJU
5/23qui
multi-stopAmerican Airlines
7h 06mSJU-BOS
$351
5/21ter
multi-stopAmerican Airlines
7h 15mBOS-SJU
5/21ter
multi-stopAmerican Airlines
7h 06mSJU-BOS
$364
5/18sáb
multi-stopUnited Airlines
12h 38mBOS-SJU
5/22qua
multi-stopUnited Airlines
8h 59mSJU-BOS
$442
5/18sáb
multi-stopUnited Airlines
8h 41mBOS-SJU
5/18sáb
multi-stopUnited Airlines
7h 32mSJU-BOS
$456

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