$126 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 5/9. 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.
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$249
Albany
Albany1 stop$304
Boston
Bostonnonstop$249
Albany
Albany1 stop$304

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

Fri, Aug 21 - Sun, Aug 23
Breeze Airways Logo
12:33 pm - 10:48 pm
SAN
-
BDL
7h 15m
1 stop
Breeze Airways Logo
7:00 am - 11:39 am
BDL
-
SAN
7h 39m
1 stop
$209Breeze Airways
Fri, Aug 21 - Sun, Aug 23
Breeze Airways Logo
12:33 pm - 10:48 pm
SAN
-
BDL
7h 15m
1 stop
Breeze Airways Logo
7:00 am - 11:39 am
BDL
-
SAN
7h 39m
1 stop
$216Breeze Airways
Fri, Aug 21 - Sun, Aug 23
Breeze Airways Logo
12:33 pm - 10:48 pm
SAN
-
BDL
7h 15m
1 stop
Breeze Airways Logo
7:00 am - 11:39 am
BDL
-
SAN
7h 39m
1 stop
$220Breeze Airways
Mon, May 18 - Sun, May 24
JetBlue Logo
8:30 pm - 5:09 am
SAN
-
BOS
5h 39mnonstop
JetBlue Logo
6:37 am - 9:52 am
BOS
-
SAN
6h 15mnonstop
$249JetBlue
Sat, May 16 - Tue, May 19
American Airlines Logo
6:40 am - 7:56 pm
SAN
-
BOS
10h 16m
1 stop
American Airlines Logo
6:00 am - 11:17 am
BOS
-
SAN
8h 17m
1 stop
$257American Airlines
Mon, May 18 - Sun, May 24
Alaska Airlines Logo
8:54 pm - 5:44 am
SAN
-
BOS
5h 50mnonstop
Alaska Airlines Logo
7:20 am - 4:21 pm
BOS
-
SAN
12h 01m
1 stop
$258Alaska Airlines
Fri, May 22 - Thu, May 28
JetBlue Logo
8:44 pm - 5:23 am
SAN
-
BOS
5h 39mnonstop
JetBlue Logo
4:15 pm - 7:33 pm
BOS
-
SAN
6h 18mnonstop
$264JetBlue
Wed, Jun 3 - Wed, Jun 10
American Airlines Logo
9:55 pm - 9:56 am
SAN
-
BOS
9h 01m
1 stop
American Airlines Logo
2:27 pm - 9:48 pm
BOS
-
SAN
10h 21m
1 stop
$267American Airlines
Wed, Aug 5 - Tue, Aug 11
Southwest Logo
10:40 pm - 9:30 am
SAN
-
ALB
7h 50m
1 stop
Southwest Logo
6:20 pm - 10:35 pm
ALB
-
SAN
7h 15m
1 stop
$362Southwest
Wed, Aug 5 - Tue, Aug 11
Southwest Logo
8:35 am - 9:20 pm
SAN
-
ALB
9h 45m
2 stops
Southwest Logo
6:20 pm - 10:35 pm
ALB
-
SAN
7h 15m
1 stop
$367Southwest
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.

How much is a round-trip flight from San Diego to Massachusetts?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from San Diego to Massachusetts departing in May.

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 $169 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 $169.

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

The average price for all round-trip flights from San Diego to Massachusetts depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Massachusetts is generally at night, when round-trip flights cost $333 on average. Morning departures are around 30% 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 $453.

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 $371, 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 May, when tickets cost $98 (return) on average. On the other hand, the most expensive months are November and June, when the average cost of round-trip tickets is $1,618 and $678 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 Wednesday, 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 6 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$126
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 16% lower on average.
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.

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 $169 one-way - $305 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.
7.9
Alaska AirlinesOverall score based on 12315 reviews
7.8Comfort
7.0Entertainment
8.5Crew
7.1Food
8.1Boarding
Airline reviews

More efficient with checking lines and boarding/checking bags when needed.

4.0 OkayAnonymous, Apr 2026
SAN - JFK
Read more Alaska Airlines reviews

More efficient with checking lines and boarding/checking bags when needed.

They were really helpful with every question and my kids had never been on a plane and the staff made them feel comfortable

I was on flight #3022 departed from San Diego, California to Medford, Oregon. I had Denise & Damaris as my flight attendants. I didn’t have much interaction with Damaris, but I did with Denise who had, this calm, cool collective voice when she spoke about the emergency exit plans before takeoff. I travel often and I’ve never met a flight attendant that can put you at ease. I felt she respects and takes pride in her position and more airlines need to adopt the integrity and respect that she has for Alaska Airlines. Debbie

All airlines should board planes back to front, instead of catering to higher priced tickets. The boarding groups are inefficient and delay takeoff time

Luggage was severely damaged. Flight was late for several hours

The ticketing counter in SD was a mess. The lady handling the First-Class check-in seemed overwhelmed until a supervisor replaced her. It took almost 20 minutes to get once couple checked in, and then she started walking around the counters while 7 people just stood in line. Once her supervisor arrived, she announced she was going on break, never to engage with customers again.

No outlets, plugs, way to charge the phone or service and no food on one leg o the trip, but other than that, great. Loved WIFI, the flight, the crew, the pilots, the schedule, etc. Great job. My new favorite airline!

I had a problem with my reservation and no one could help me understand what happened. I booked my flight months ago and received a confirmation email. In the confirmation email, it said that the flight would depart at 3:15 p.m. A few hours before the flight, I tried to go online and check in, and suddenly it said that the flight was leaving an hour earlier. I had to rush to get to the airport and almost didn't make it. No one could help me understand why this happened, and I'm really concerned that it might happen in the future. I would appreciate some support in this matter.

It was a super old plane so the first class experience was just not luxurious

Good as usual. Just wished my seat was assigned at online check in. Thanks anyways

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

The tray table was broken and the food was terrible.

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

N Everything was perfect from boarding to assistance to baggage in Tampa

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I took seat 15A in anticipation of window seat, there is no window.

Fabulous if you have a portable wheelchair. They can store it in the galley and you can just walk out with it. Really nice and the flat seats are just incredible, very nice. iPads for movies, also pretty nice,

No charging outlets worked. Other than collecting trash attendants didn’t come around. No one could hear flight attendants announcements during the flight. Seat pads were horrible. Sitting on a board for 5 hours. What happened to Hawaiian airlines comfort, hospitality, and extras? Our pilots did an excellent job trying to minimize turbulence and incredible job in landing in windy conditions.

I like that if they asked you to checked in a bag at the gate they give you priority to board

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.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

Entertainment and wifi were very sub-par - audio issues and no wifi

They forced me to check my hand luggage at the gate.

Still hasn’t left. Why are you asking how it was?

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

Boarding gate at LAX was too crowded—two gates next to one another

On time departure and early arrival. Flight attendant very nice.

The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

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

Information on your arrival and departure airports