$119 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 12/16. 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, 0 bags

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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
Bostonnonstop$198
Albany
Albany1 stop$372
Boston
Bostonnonstop$198
Albany
Albany1 stop$372

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 - Sat, Dec 13
JetBlue Logo
9:20 pm - 5:49 amSAN-BOS
5h 29mnonstop
JetBlue Logo
4:34 pm - 8:10 pmBOS-SAN
6h 36mnonstop
$198JetBlue
Find Deal
Sat, Dec 6 - Sat, Dec 13
JetBlue Logo
9:05 pm - 7:42 amSAN-BOS
7h 37m1 stop
JetBlue Logo
4:34 pm - 8:10 pmBOS-SAN
6h 36mnonstop
$205JetBlue
Find Deal
Thu, Nov 13 - Wed, Nov 19
Alaska Airlines Logo
9:15 am - 5:55 pmSAN-BOS
5h 40mnonstop
Alaska Airlines Logo
4:24 pm - 8:03 pmBOS-SAN
6h 39mnonstop
$215Alaska Airlines
Find Deal
Sat, Dec 6 - Thu, Dec 11
Delta Logo
10:20 pm - 6:50 amSAN-BOS
5h 30mnonstop
Delta Logo
5:25 pm - 8:59 pmBOS-SAN
6h 34mnonstop
$222Delta
Find Deal
Thu, Nov 13 - Mon, Nov 17
Alaska Airlines Logo
8:08 pm - 3:41 pmSAN-BOS
16h 33m1 stop
Alaska Airlines Logo
4:24 pm - 8:03 pmBOS-SAN
6h 39mnonstop
$227Alaska Airlines
Find Deal
Thu, Nov 27 - Thu, Dec 4
American Airlines Logo
6:20 am - 6:28 pmSAN-BOS
9h 08m1 stop
American Airlines Logo
3:35 pm - 9:44 pmBOS-SAN
9h 09m1 stop
$238American Airlines
Find Deal
Tue, Feb 10 - Tue, Feb 24
Hawaiian Airlines Logo
9:10 am - 5:44 pmSAN-BOS
5h 34mnonstop
Hawaiian Airlines Logo
7:00 am - 4:37 pmBOS-SAN
12h 37m1 stop
$240Hawaiian Airlines
Find Deal
Tue, Feb 10 - Tue, Feb 24
American Airlines Logo
9:24 am - 8:30 pmSAN-BOS
8h 06m1 stop
American Airlines Logo
7:15 am - 1:36 pmBOS-SAN
9h 21m1 stop
$246American Airlines
Find Deal
Tue, Mar 3 - Wed, Mar 4
Hawaiian Airlines Logo
9:15 am - 6:09 pmSAN-BOS
5h 54mnonstop
Hawaiian Airlines Logo
4:20 pm - 7:44 pmBOS-SAN
6h 24mnonstop
$247Hawaiian Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Delta Logo
10:00 pm - 8:48 amSAN-BDL
7h 48m1 stop
Delta Logo
6:09 am - 11:14 amBDL-SAN
8h 05m1 stop
$299Delta
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 $140 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 $140.

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 $347, 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 $266 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $440 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 50% 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$119
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 7% 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 $327 on average. Morning departures are around 36% 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 $470.

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 $183 one-way - $260 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 11220 reviews
7.8Comfort
7.0Entertainment
8.1Boarding
7.1Food
8.5Crew
Airline reviews

I recently traveled with my service animal, and before boarding, a gate agent kindly arranged for me to have an empty seat next to me to give my dog more space. However, once on board, a male crew member spoke to me in a rude and loud tone, insisting my dog stay on the floor or my lap—even after I explained what the gate agent had approved. His tone and behavior were unprofessional and made me feel uncomfortable in front of other passengers. I understand and respect airline policies, but I would appreciate if this could be reviewed to ensure better awareness and sensitivity toward passengers traveling with service animals. Thank you for your understanding.

6.0 GoodSofia, Oct 2025SAN - DCA
Read more Alaska Airlines reviews

I recently traveled with my service animal, and before boarding, a gate agent kindly arranged for me to have an empty seat next to me to give my dog more space. However, once on board, a male crew member spoke to me in a rude and loud tone, insisting my dog stay on the floor or my lap—even after I explained what the gate agent had approved. His tone and behavior were unprofessional and made me feel uncomfortable in front of other passengers. I understand and respect airline policies, but I would appreciate if this could be reviewed to ensure better awareness and sensitivity toward passengers traveling with service animals. Thank you for your understanding.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

It was the most expensive Alaska Airlines ticket I’ve ever purchased. I had a middle seat with no legroom or space compared to any other middle seat I’ve hadThere was a silver box under the seat that took up 70% of my legroom on the most narrow 737 max the crew flat out would not help they would not help with bags they would not help with garbage there was no coffee,It was definitely not one of my better experiences on Alaska.

Sitting on the ground for 2 hours waiting for a gate wasn't fun.

It was a great experience, friendly staff and good snacks

Very mediocre, and disappointing for the price of the ticket

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.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

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.

I received several emails about my 3:10 flight. When I showed up to the airport at 12:30 to check my bags I was told the flight was actually at 1 pm. They grudgingly rebooked me for a flight at 5:22 to Vegas to get a connecting to LAX. I did find the gate for my original 3:10 flight but they were booked. I proceeded to receive status updates and gate change information for the 3:10 flight, even though I was apparently never supposed to be on that flight

The food options were limited and very specific. Some type of entertainment option for a 4.5 hour flight would have been nice.

The Kayak confirmation number did not work for checking in the day before. I checked in at 8.30 using my ticket number. When I arrived at the airport, I was informed that the flight was overbooked, and since I had checked in late, I did not have a seat. The Next flight was not until ten PM. I called my wife, who had been taking care of our kids all weekend, and she was upset, calling me a liar and telling me to stay in SD. It turned my weekend getaway into a nightmare! I blame the Kayak website and will not book flights using your app in the future.

comfortable but the food is horrible. I have flown Hawaiian several times now and no matter what they say the food is its the same squashed bread with melted goop inside. Tastes fake and isnt what they represent, its quite nasty. What happend to real food? And there is NO entertainment!! so not sure why they are asking for a review on that.

Good and friendly staff. Nicely enjoyed the complimentary drink and snack.

I was very, very cold and a stranger loaned me her sweater next to me. I didn’t wanna buy a blanket just for a four hour trip when I did not need the pillow or the earphones. I don’t mind purchasing a blanket, but I only needed that not all of it accessories. Cold air pretty much blew the entire trip. Two people in front of me both bought the blanket packages. Maybe that’s the idea. The crew was exceptionally nice and passed through multiple times.. the restrooms were very clean and usually accessible.

3 hour wait on customer service after flight was cancelled. Was bumped to a flight where I wouldnt have gotten to my destination for another 2 days. Had to fully refund flight and book a new one the following morning. Paid twice the amount for the flight than I had originally booked. Very disappointed I was not offered any sort of discount or points for all of the frustration, in fact the airline profited twice as much off of me by cancelling my flight and and changing my entire trip.

I understand that both Hawaiian and Alaskan are in the process of merging but I could not get real-time flight info or access my boarding pass on either app

Had a hard time checking into my flight on my phone because they gave me the wrong confirmation number. Otherwise everything else went well.

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

The flight was flawless and we even arrived between 20 and 25 minutes early!

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

Very crowded flight but what can you expect these days?? Crew was accommodating.

They only offered water for Group 6. Awful announcements from the Crew. Couldn't understand a single word. Barely came by for the trash afterwards. Man, I love water for a premium flight. Wow. Water in a cup.

The seats in economy were appeared to be quite thin and lack sufficient cushioning to be comfortable. Perhaps it was my seating position but the plane seemed notably load.

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.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Friendly crew. Poor food service maybe due to full flight. All in all, you get what you pay for.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

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.

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