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Find cheap flights from San Diego to Massachusetts from $60

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Diego to Massachusetts departing on 5/29. 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
Sat 6/1
Sat 6/8

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Best Massachusetts Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Boston
Boston2 stops$103
West Tisbury
West Tisbury2 stops$291
Albany
Albany1 stop$405

Good to know

Low season

January

High season

October

Cheapest flight

$60
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 20% lower on average.
Flight from San Diego to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from San Diego to Massachusetts?

    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 San Diego to Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Massachusetts from San Diego 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 San Diego to Massachusetts?

    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 Massachusetts with an airline and back to San Diego with another airline.

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

    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 Massachusetts from San Diego up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Massachusetts

  • Looking for a cheap flight? 25% of our users found tickets from San Diego to the following destinations at these prices or less: Boston $191 one-way - $252 round-trip
  • Morning departure is around 26% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from San Diego to Massachusetts

 
Need help choosing which airline to fly with from San Diego to Massachusetts? 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.
8.0
DeltaOverall score based on 10861 reviews
8.6Crew
8.0Entertainment
8.2Boarding
7.9Comfort
7.4Food
Airline reviews

There was a loud squeaky sound the whole time we were flying.

6.0 GoodEliza, Apr 2024SAN - LAX
Read more about Delta reviews

There was a loud squeaky sound the whole time we were flying.

I didn’t not like that I could not select my seat and ended up with the worse seat.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Plane was late because of a mechanical malfunction and the food listed as available was not. Flight attendants seem over worked and under paid. They just done seem happy. And that can be seen in their faces.

Terrible. Delta delays caused us to miss our flight and they did nothing to fix it.

Waited 3 hours on a plane to de-ice due to manpower issues. Waited another hour and a half once we landed because of a gate issue. Missed my connections. Created. A total of 13 hours of delay.

Great, on time departure, friendly and accommodating crew, great leg room, Smith flight

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

Like most domestic flights in the US, you are basically on your own with this airline when it comes to food, so be sure to purchase meals and drinks ahead of time or expect to arrive starving and dehydrated (like I was).

You need to be a hacker to get the (Free) WiFi

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Delayed by almost an hour - I also noticed that all JetBlue flights departing from PBI were delayed yet the weather was perfect.

I loved the wifi, much better than Delta. Seats were old. and bathrooms dingy.

There was no wheelchair or wheelchair escort at the gate..unacceptable

Delayed 4 hours because of maintenance issue they knew about all day. Get another plane. Time is precious!

I liked that boarding and take off were timely despite a 15 minute delay due to weather. The pilot communicated with us the entire flight keeping us informed re: turbulance and slight delays on the runway after we landed.

Has been always great except flight cancelation in the past at very last minute waiting till 2am and we when have to beg for overnight accommodation

There were weather issues and coding problems whatever those refer to, but JetBlue, for two days in a row was unbelievably late. Several hours late, resulting in almost no sleep for passengers like me.

The plane was very hot. There were delays . Generally, the flight was great.

If jet blue is going to offer tv at every seat, fix the headphone connection so you can hear. Haven’t had a usable headphone jack in years

I paid $380 for my one-way ticket from California to Minnesota. The fair did not include online check-in. I received instructions from their app to check in at a kiosk. At the kiosk, the boarding pass would not print until an actual person came to verify that I had a personal item and not a carry-on item, On the plane, the person next to me was drunk and allowed to continue to order alcohol. United is garbage I’d rather fly spirit.

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

Terrible! The plane was old and you are required to connect your own device to their Wi-Fi rather than have entertainment options in the back of the seat in front of you. The Wi-Fi went out during the flight and there was only one plug for the devices every two seats. Three out of five surrounding my family did not work. The seats and spaces under them were so small I could not fit my backpack, which I’ve always brought on flights and fit before no problem. The crew were unpleasant and patronizing.

Due to one crew member not showing up to work, our flight was significantly delayed causing us to miss our connecting flight in Houston to Mississippi causing us to be delayed by more than 6 hours and missing our event all together. Very disappointing. All because ONE crew member called in sick. United did grant us a $15 meal voucher, which was a small but appreciated concession that I wasn’t able to use because I ordered my lunch and paid for it before applying the concession, and the staff said it was too late to use it. Ugh! We also had a TWO delay coming back from Mississippi, but that was on American Airlines and it was due to weather, so not their fault. Anyway, not at all impressed with United’s handling of our flight and the HUGE disappointment of missing our important family event for our 90 year old mother. All that money and all that stress and emotions for nothing. Having to wait the hour to bring an employee from LAX seemed like something that should not have happened. Why don’t you have a local back-up? Santa Ana is not a little airport in a rural area.

Crew was great and did their best to make us comfortable and captain came out at the beginning to announce why the flight was delayed, weather situation up ahead, and kept us updated throughout the flight.

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Awful. I got stuck next to a person carrying a dog and behind someone with a dog. People need to board these dogs downstairs. The cabin is crowded enough with your pets

Packed in like sardines, very uncomfortable. Sitting the aisle my shoulder was rammed into numerous times by rushing flight attendants. Also flight was very cold.

the head jack on my seat didn't work and the power outlet didn't work for my seat

Left 2 hours later for delayed I had to take care a kid with special need since people don’t want to move to accommodate the rest of the family. . It wasn’t bad but that made me upset that people can be that selfish.

The experience was great and much better than the flight going out. of course I was in first class but the service was excellent

Comfort of seats, ease of boarding. Food selection could be better

Food options were limited which is absolutely embarrassing for a Flight of this size The staff did not come around as much and I am not accustomed to such poor service from American Airlines Drinks I believe were limited to soda and water

Crew were attentive and friendly. Flight was smooth and early! I enjoyed the less crowded plane. Thank you!

Delayed abs delayed Gate crew giving poor info - we are definitely leaving at —- Ultimately to cancel flight after 4+ hours of delays Just cancel it earlier

We are gluten free, there were not any available complimentary gluten free options.

No meal on a cross country flight? SFO-MiA is pretty much the definition of a coast to coast flight. No meal provided. Sky high wi-fi rates too. Stop nickel and diming your customers.

The staff was unprofessional and didn’t communicate very well. The boarding process was very disheveled, potentially due to a power outage the previous day but there was no contingency plan to properly get passengers boarded the following day. Once boarded the aircraft stayed on the tarmac for over 45 minutes due to high winds. The communication was sporadic but an announcement was finally made an additional 30 minutes later that the flight was cancelled but we couldn’t get off the plane. Prior to deplaning one of the gate agents came on the plane and made an announcement for everyone to pickup their checked bags and take a card to rebook a new reservation because they didn’t have adequate staff. Flights were missed, passengers went to different airports and there was little to no assistance from AA.

Apart from the delay due to unforeseen circumstances. The leg from sjc to dfw was fine. It was the leg from dfw to orf that we encountered issues mainly due to the flight attendant crew not being friendly. We had two small children and we needed some assistance to warm up milk so the baby would sleep. The crew just didn’t get it and made things very difficult. One made a remark that the baby’s dirty diaper smell was a “gift” to the plane in a rude way. Normally I’d brush that off as a funny comment if the rest of the trip the attendants were helpful or understanding of the difficulty we faced. But that wasn’t the case. We were met with rudeness on the second leg. Whereas on the first leg the crew were so nice and helpful.

Flight From PHX to CVG was on time, very professional staff

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Terrible. Seats are bad and the baggage policy is inconsistent

Better than I expected but I did pay for a seat and carry on bags ahead of time.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

Book cheap flights from San Diego to Massachusetts

Recent round-trip flight deals

5/28Tue
2 stopsSpirit Airlines
15h 01mSAN-BOS
5/29Wed
1 stopSpirit Airlines
12h 26mBOS-SAN
$103
5/20Mon
3 stopsSpirit Airlines
17h 30mSAN-BOS
5/29Wed
1 stopSpirit Airlines
12h 26mBOS-SAN
$128
5/20Mon
2 stops
22h 36mSAN-BOS
5/21Tue
1 stop
13h 07mBOS-SAN
$176
5/17Fri
1 stop
27h 37mSAN-BOS
5/21Tue
1 stop
13h 07mBOS-SAN
$198
9/25Wed
2 stopsAmerican Airlines
24h 50mSAN-ORH
10/2Wed
2 stopsAmerican Airlines
25h 11mORH-SAN
$236
8/16Fri
2 stopsAmerican Airlines
24h 08mSAN-ORH
8/28Wed
2 stopsAmerican Airlines
10h 37mORH-SAN
$276
6/1Sat
2 stopsDelta
12h 37mSAN-MVY
6/5Wed
1 stopDelta
8h 10mMVY-SAN
$291
6/1Sat
2 stopsDelta
10h 22mSAN-MVY
6/5Wed
2 stopsDelta
11h 01mMVY-SAN
$327
8/24Sat
1 stopJetBlue
10h 24mSAN-HYA
8/28Wed
1 stopJetBlue
10h 43mHYA-SAN
$859
9/25Wed
1 stopJetBlue
9h 25mSAN-PVC
10/2Wed
1 stopJetBlue
10h 41mPVC-SAN
$860

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Recent one-way flight deals

5/29Wed
1 stopSpirit Airlines
9h 13mSAN-BOS
$60
6/3Mon
2 stopsSpirit Airlines
18h 21mSAN-BOS
$64
6/7Fri
nonstopDelta
5h 44mSAN-BOS
$169
8/1Thu
1 stopAmerican Airlines
9h 15mSAN-BOS
$173
7/22Mon
1 stopAmerican Airlines
9h 15mSAN-BOS
$178
5/21Tue
nonstopDelta
5h 41mSAN-BOS
$192
5/18Sat
1 stopJetBlue
8h 03mSAN-BOS
$196
5/22Wed
nonstopJetBlue
5h 32mSAN-BOS
$218
8/5Mon
2 stopsUnited Airlines
9h 43mSAN-BOS
$233
7/28Sun
1 stopUnited Airlines
7h 53mSAN-BOS
$240

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Last minute flights from San Diego to Massachusetts

Last minute flight, train and bus deals

5/7Tue
multi-stopSpirit Airlines
16h 13mSAN-BOS
5/14Tue
multi-stopSpirit Airlines
13h 07mBOS-SAN
$157
5/7Tue
multi-stopSpirit Airlines
26h 00mSAN-BOS
5/14Tue
multi-stopSpirit Airlines
13h 07mBOS-SAN
$173
5/7Tue
nonstopJetBlue
5h 32mSAN-BOS
5/8Wed
nonstopJetBlue
6h 10mBOS-SAN
$437
5/6Mon
nonstopJetBlue
5h 34mSAN-BOS
5/31Fri
nonstopJetBlue
6h 13mBOS-SAN
$476
5/7Tue
nonstopAlaska Airlines
5h 55mSAN-BOS
5/16Thu
nonstopAlaska Airlines
6h 20mBOS-SAN
$498
5/7Tue
multi-stopAlaska Airlines
9h 09mSAN-BOS
5/16Thu
nonstopAlaska Airlines
6h 20mBOS-SAN
$507
5/3Fri
multi-stopAmerican Airlines
8h 20mSAN-BOS
5/13Mon
multi-stopAmerican Airlines
8h 52mBOS-SAN
$512
5/7Tue
nonstopAmerican Airlines
5h 55mSAN-BOS
5/14Tue
nonstopAmerican Airlines
6h 22mBOS-SAN
$518
5/7Tue
nonstopDelta
5h 41mSAN-BOS
5/18Sat
multi-stopDelta
12h 23mBOS-SAN
$532
5/7Tue
nonstopDelta
5h 41mSAN-BOS
5/18Sat
nonstopDelta
6h 13mBOS-SAN
$540

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San Diego - Massachusetts Flights

Departure:

San Diego (SAN)United States

Return flight deals:

Massachusetts - San Diego

Cabin classes:

$656
$1,256
$538
$163