$88 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 9/18. 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$205
Albany
Albany1 stop$287
Boston
Boston1 stop$205
Albany
Albany1 stop$287

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

Tue, Aug 26 - Sun, Aug 31
Breeze Airways Logo
12:41 pm - 10:52 pmSAN-BDL
7h 11m1 stop
Breeze Airways Logo
6:10 am - 10:51 amBDL-SAN
7h 41m1 stop
$147Breeze Airways
Find Deal
Thu, Sep 25 - Mon, Sep 29
Spirit Airlines Logo
6:15 am - 9:16 pmSAN-BDL
12h 01m2 stops
Spirit Airlines Logo
6:10 am - 6:42 pmBDL-SAN
15h 32m2 stops
$184Spirit Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
JetBlue Logo
8:55 pm - 5:40 amSAN-BOS
5h 45mnonstop
JetBlue Logo
3:45 pm - 6:58 pmBOS-SAN
6h 13mnonstop
$229JetBlue
Find Deal
Sat, Sep 6 - Sat, Sep 13
Delta Logo
10:05 pm - 6:50 amSAN-BOS
5h 45mnonstop
Delta Logo
4:15 pm - 7:18 pmBOS-SAN
6h 03mnonstop
$237Delta
Find Deal
Fri, Oct 3 - Fri, Oct 31
JetBlue Logo
10:11 am - 10:29 pmSAN-BDL
9h 18m1 stop
JetBlue Logo
7:00 am - 2:11 pmBDL-SAN
10h 11m1 stop
$247JetBlue
Find Deal
Sat, Sep 6 - Sat, Sep 13
Alaska Airlines Logo
7:59 pm - 3:00 pmSAN-BOS
16h 01m1 stop
Alaska Airlines Logo
7:45 am - 10:50 amBOS-SAN
6h 05mnonstop
$247Alaska Airlines
Find Deal
Tue, Sep 16 - Sat, Sep 20
Alaska Airlines Logo
10:18 pm - 3:00 pmSAN-BOS
13h 42m1 stop
Alaska Airlines Logo
8:23 pm - 7:41 amBOS-SAN
14h 18m1 stop
$256Alaska Airlines
Find Deal
Sat, Oct 4 - Wed, Oct 8
American Airlines Logo
10:32 pm - 9:11 amSAN-BDL
7h 39m1 stop
American Airlines Logo
4:00 pm - 9:21 pmBDL-SAN
8h 21m1 stop
$275American Airlines
Find Deal
Thu, Sep 25 - Mon, Sep 29
American Airlines Logo
11:46 am - 12:28 amSAN-BDL
9h 42m1 stop
American Airlines Logo
6:00 am - 11:36 amBDL-SAN
8h 36m1 stop
$277American Airlines
Find Deal
Fri, Aug 22 - Wed, Sep 3
Delta Logo
10:40 pm - 1:33 pmSAN-MVY
11h 53m2 stops
Delta Logo
11:44 am - 9:15 pmMVY-SAN
12h 31m2 stops
$297Delta
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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from San Diego to Massachusetts.

The cheapest ticket to Massachusetts from San Diego found in the last 72 hours was to Boston, at $151 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 $151.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $433 on average.

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 $262 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $474 and $399 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 45% 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$88
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from San Diego to Hartford

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 $331 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 $495.

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 $167 one-way - $274 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
7.8Comfort
8.1Boarding
8.5Crew
7.1Entertainment
7.1Food
Airline reviews

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.

10.0 ExcellentAnonymous, Jul 2025SAN - JFK
Read more Alaska Airlines reviews

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

The plane was delayed a bit. It wasn't a huge problem though, as we were heading back home.

Flight was great. Boarding was crazy because another flight was boarding late next to ours so everyone was standing and in the way.

very good but no blankets for overnight flight or tv screens…

We were in 1st Class. Excellent service. Easy boarding. No too difficult to speak with someone on the phone. Breakfast was not eatable for me. No screen to watch movies. I don't have or want a tablet. This is first class there should be screens. Even if I had a tablet there was no place to put it. There is a place to put a tablet in economy. Seats were a bit lumpy.

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.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

Flight got delayed and it was very inconvenient . Had to come with another carrier. Had to spend one more night in San Francisco.

Everything was good for the price I paid. Crew was very nice.

The worst flight experience I've ever had. Our flight was delayed 14 whole hours because the flight crew never showed up. We had to wait in a two hour line to get our new boarding passes, we were told we had no other option but to fly at 10pm (we didn't depart until 11:45pm). Everyone had to contact their hotels and car rental places, workplaces, etc. since we lost an entire day's worth of travel. The crew showed up at 10:15, which was past the time we were supposed to board. They were laughing and being completely smug when they boarded, and they took another hour to board us onto our flight. The flight crew never came to check in on us, we were quickly given one drink and sandwich and they turned off the lights and were negligent the rest of the trip. My mom asked three attendants for a seat belt extender, they never brought one. I was dehydrated and never received another drink. They were very rude and unfriendly, we had been up since 4am the morning of our flight and didn't land in our destination until 2am the next day (5am local time). This was unacceptable service and treatment, these flights are not cheap and we were inconvenienced out of an entire day of travel. This was 100% avoidable and was the fault of Hawaiian Airlines, and their crews inability to show up to work on time.

Loved the leg room, usb charging, outlet, food, staff. The seats were very uncomfortable for some reason and made my buttocks ache and would have liked to be seated together from the time of purchasing tickets without having to pay extra.

I was put in seat 6B with no warning. Had no seat in front of me just sticks out in the aisle so I had to hold what I could and put the rest in a bin way further down.

Usually we have a pleasant trip on HA. Not this time! All stewards were unpleasant, rude, rushed, condescending. First step onto the plane, WE greeted the crew with an “Hello!”. They greeted us with a terse smile then ignored us. Not a good start. Even over the PA announcements, they were rushed and unpleasant. One Stewart even berated a passenger in front of us when all they asked is if the purchase cart had vodka to purchase. The steward said “LIKE WE SAID OVER THE PA, THIS ONLY HAS FOOD OR BEVERAGE!” Vodka is a beverage! It was a legitimate question. Not sure why she treated the passenger this way. Taking trash was even unpleasant, No “Thank you” or at least a smile. I work in CS. I know good CS can make or break your trip. There was absolutely no “aloha” on this trip. All clearly did not want to be on this plane and felt strongly that they did not want to provide a premium service to their clients. This might be our last HA and cancellation of my HA-MC if we are treated the same way going home. We are typically treated with kindness and warmth in the past with HA. This trip was unacceptable.

Overall it was a good flight, but the food should be looked at. No options. The seat was also uncomfortable and very tight.

I was unable to get a check im and get a boarding pass. I tried at the desk of the flight operator Alaska, was told to go to Hawaiian and almost had to go back to Alaskan. In the end inwas told to go thru security and directly to the gate without checking in. It would have been more helpful to have the details rather than walking all over the terminals trying to check in.

The middle name gave us so much issue at check in we had done middle names when booking but Hawaiian/Alaska don’t recognize the middle names and gave us problems at check in. We have never experienced that before.

I was booked thru Hawaiian Airlines (HA) on Kayak in February. I got 2 confirmation emails from Hawaiian Airlines in February. Even though the flight ticket informed me the flight was marketed thru HA and operated by Alaska Airlines (AA), I was never given any confirmation codes or anything from Kayak or AA to check into my flight online ahead of time. They also couldn't find the HA flight number I was given on their website and was told my flight did not exist unless I searched thru the AA website for flight details that was similar to the info HA gave me. The only way to check into my flight and make sure the flight still existed required me to get there 4 hours early. When I arrived at the airport, HA desk told me to go to AA desk. First AA desk redirected me to another desk, second AA desk told me to find someone with an iPad, and finally the iPad rep was able to help me. I also had to chat with AA reps online the night previous to my return trip because the same issue occurred.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

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

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.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

Cramped seats. FAA should make airlines have more legroom, for even short people complain

Flight was full, and would have preferred an aisle seat, but due to getting a late ticket ,the seat I had was adequate. The flight crew were very help full and hard working. Food and drink were excellent for the 11hr flight. Overall I was pleased with flight, and would recommend British Airways again.

Eventless. It was a good flight and good crew. Can’t complaint.

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

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