$127 Find Cheap Flights from San Diego to Massachusetts

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 9/26. 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
1 adult, Economy

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Diego to Massachusetts.
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Cheap Flights from San Diego to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$174
Albany
Albany1 stop$307
Boston
Boston1 stop$174
Albany
Albany1 stop$307

Book Cheap San Diego to Massachusetts Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Diego to Massachusetts that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Diego to Massachusetts

Sat, Dec 6 - Wed, Dec 10
Southwest Logo
7:00 am - 5:05 pmSAN-BOS
7h 05m1 stop
Southwest Logo
6:45 am - 2:15 pmBOS-SAN
10h 30m1 stop
$174Southwest
Find Deal
Sat, Dec 6 - Wed, Dec 10
Southwest Logo
7:40 pm - 8:05 amSAN-BOS
9h 25m2 stops
Southwest Logo
6:45 am - 2:15 pmBOS-SAN
10h 30m1 stop
$179Southwest
Find Deal
Sat, Dec 13 - Tue, Dec 16
JetBlue Logo
9:20 pm - 5:49 amSAN-BOS
5h 29mnonstop
JetBlue Logo
6:52 am - 10:28 amBOS-SAN
6h 36mnonstop
$229JetBlue
Find Deal
Tue, Nov 18 - Wed, Dec 3
Delta Logo
10:28 pm - 6:55 amSAN-BOS
5h 27mnonstop
Delta Logo
5:25 pm - 8:58 pmBOS-SAN
6h 33mnonstop
$232Delta
Find Deal
Thu, Dec 4 - Tue, Dec 9
Alaska Airlines Logo
5:26 pm - 7:40 amSAN-BOS
11h 14m1 stop
Alaska Airlines Logo
4:24 pm - 8:10 pmBOS-SAN
6h 46mnonstop
$237Alaska Airlines
Find Deal
Tue, Nov 18 - Thu, Dec 4
JetBlue Logo
2:52 pm - 11:16 pmSAN-BOS
5h 24mnonstop
JetBlue Logo
4:06 pm - 7:35 pmBOS-SAN
6h 29mnonstop
$242JetBlue
Find Deal
Thu, Dec 4 - Tue, Dec 9
Alaska Airlines Logo
6:30 pm - 7:40 amSAN-BOS
10h 10m1 stop
Alaska Airlines Logo
9:00 am - 4:57 pmBOS-SAN
10h 57m1 stop
$256Alaska Airlines
Find Deal
Sat, Nov 8 - Tue, Nov 11
American Airlines Logo
6:19 am - 8:30 pmSAN-BOS
11h 11m1 stop
American Airlines Logo
6:00 am - 11:43 amBOS-SAN
8h 43m1 stop
$263American Airlines
Find Deal
Mon, Oct 27 - Thu, Oct 30
American Airlines Logo
6:20 am - 5:26 pmSAN-BOS
8h 06m1 stop
American Airlines Logo
2:18 pm - 7:24 pmBOS-SAN
8h 06m1 stop
$268American Airlines
Find Deal
Fri, Oct 24 - Mon, Oct 27
Delta Logo
10:15 pm - 6:53 amSAN-BOS
5h 38mnonstop
Delta Logo
5:25 pm - 8:44 pmBOS-SAN
6h 19mnonstop
$292Delta
Find Deal
Booking Insights

KAYAK's insights & trends for San Diego to Massachusetts flights

Get data-powered insights and trends into flights from San Diego to Massachusetts to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest San Diego to Massachusetts flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Massachusetts from San Diego found in the last 72 hours was to Boston, at $118 round-trip. The most popular route is from San Diego (SAN) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $118.

Can I save money by flying with a layover from San Diego to Massachusetts?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $330, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from San Diego to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Diego to Massachusetts, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from San Diego to Massachusetts is January, when tickets cost $264 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $467 and $398 respectively.

What’s the cheapest day of the week to fly from San Diego to Massachusetts?

The average price of all round-trip flights from San Diego to Massachusetts clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Massachusetts on a Wednesday and more expensive on a Sunday. On your return trip to San Diego, you should consider flying back on a Tuesday, and avoid Sundays for better deals.

How far in advance should I book a flight from San Diego to Massachusetts?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from San Diego to Massachusetts, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from San Diego to Massachusetts, you should book around 4 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$127
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 4% 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 from San Diego to 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 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 from San Diego to Massachusetts with an airline and back 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 from San Diego to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally at night, when round-trip flights cost $329 on average. Morning departures are around 40% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the morning, which is peak travel time and where the average cost of a ticket is $484.

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 $171 one-way - $257 round-trip

Reviews of the top 5 airlines serving from San Diego to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from San Diego to Massachusetts. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
Alaska AirlinesOverall score based on 10000 reviews
8.5Crew
7.8Comfort
7.0Entertainment
8.1Boarding
7.1Food
Airline reviews

My flight wait is 3 hours delayed due to Unknown reason. We waited a very long time in the tarmac. Our flight 24 was scheduled @ 7, therefore we left my house at 330 to park our car. We were at the gate @ 530, then we were told at 6a that it will be late , we boarded at 930 but did not take off until 1015. Therefore my arranged pick up in JFK was cancelled because of no show. Before all these I got an email offers of changing my flight to a different date which I took a day earlier. I will never again take Alaska Airlines, very Inefficient and Disappointing.

10.0 ExcellentGRACE, Aug 2025SAN - JFK
Read more Alaska Airlines reviews

My flight wait is 3 hours delayed due to Unknown reason. We waited a very long time in the tarmac. Our flight 24 was scheduled @ 7, therefore we left my house at 330 to park our car. We were at the gate @ 530, then we were told at 6a that it will be late , we boarded at 930 but did not take off until 1015. Therefore my arranged pick up in JFK was cancelled because of no show. Before all these I got an email offers of changing my flight to a different date which I took a day earlier. I will never again take Alaska Airlines, very Inefficient and Disappointing.

Such great crew, from checkin to the plane. So friendly and helpful, I was genuinely impressed.

Seats extremely uncomfortable, no entertainment, no snacks, and when boarding, half of the passengers needed to check in the carry on luggage without any explanation.

The flight was jumping between being delayed and closer to schedule about 5 times. Alaska air website showed incorrect times while google had latest info. This panic was horrible to deal with.

I always heard this was a terrible airline but I was happy to experience otherwise. The seats were more comfortable than delta. They did board late and gate was a little chaotic, which is to be expected for a budget airline. I would definitely do it again for that price.

Very expensive for short flights. Can’t communicate with Alaska Air about passport issue at check-in. Also no replies to my text messages. Wanted to extend our vacation for two more days but this expensive flight ticket is called SAVER and I couldn’t make changes or cancel or get a credit even, so I paid another airline for the return trip. Extremely disappointed.

They canceled my flight then changed me $155 for the same flight the next day

Our flight time was drastically changed which caused us to lose a day of vacation

I like the new adjustable headrest. Unfortunately 2 crying children were in front of us. But it was the first time and not holding Alaska accountable for that. Alaska always seems to have everything in order professional but comfortable.

Very bad, terrible food and late by 2 hours. Then no to open aircraft doors

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

All was good and they were able to seat my travel companion next to me. Thank you.

What an amazing flight. I haven’t experienced this level of service in a flight in years. This will be the only way to fly to Hawaii for me in the future.

Kayak sold me a ticket after check in time. Could not check in. Could not get on flight.

Everything was great except having to check in at Alaska. That was a surprise and took extra time and effort. Should have been explained somewhere maybe on the HA electronic ticket.

I accidentally made this purchase and they wouldn’t refund me even though I called immediately to cancel it.

The flight was delayed and they didn’t have a pilot for the flight. Seemed very unorganized and took way longer than expected.

I could not believe that on a 5 hour plus flight we were not given a complimentary meal . That should be illegal. Or it would be nice to be informed beforehand that a complimentary meal would not be provided. The wording in the email I got about pre ordering food was phrased in a way that made the food seem like it would be free. Very misleading! Also during boarding we were informed there would be empty seats we could move to if we wanted, all we had to do was wait for an announcement, however an announcement was never made. Then when we tried to change seats ourselves we were singled out over the loud speaker and told we could not move without asking. Then the flight was about to take off , so we didn’t have time to ask . Then we were told we could not move to the exit row because you had to pay for those seats, but we were not told where we could move. Also no one was in the exit rows so , if something happened no one would be there to assist the passengers. Also people should be allowed to move there if the airline wasn’t able to sell them. One passenger asked if he could pay for the upgrade and the flight attendant said she did not have the capability to charge for the seat on her mobile device, so the airline ended up losing possible income anyways . So why not let people move there during flight if you have no way to charge them? Then the landing was bumpy and awful and many passengers complained out loud when we landed .

It was pretty good except there was no food, which was understandable because it was a short flight but I would have liked to at least have a snack; otherwise it was great. Staff/crew, great. Thank you

The flight was great! The flight attendants were friendly and attentive. I would definitely fly Hawaiian Aurlines again!

You have to buy the ear buds and they only offers little cup of water twice.

The entertainment package was vast and the selections were very current. Keep updating it was great.

The seat was so hard my tailbone was aching The crew was kind of a b**** because I made a joke that I didn't care if they close the door I total c*** when she was trying to f****** act like she was mad at me because I said that The flight was bumpy. Sure you didnt have control over that.

Ring in first class for an overnight flight, there was no blankets nor pillows for first class customers.

4 hours late, including over +1 hour waiting in plane to take off. Baggage left behind too.

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

Was not able to watch most shows on the entertainment site. They would not load

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Delayed flight, so I switched fights to SFO to Phoenix , Phoenix to DSM. Excellent service through American Airlines

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

very difficult boarding process - aggressive passengers not the friendliest crew

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

It was too hot in the cabin. The AC did not help.

Love the mosaic program, being able to move to an extra space seat for free is awesome

Everything you need to know for your flight from San Diego to Massachusetts

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