$129 Find Cheap Flights from San Diego to Massachusetts - Compare and Save

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Cheap Flights from San Diego to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Boston
5h 35mNonstop
from $236per person
Hartford
7h 00m2 stops
from $326per person
Albany
7h 03m2 stops
from $363per person
Worcester
7h 29m3 stops
from $498per person
Provincetown
11h 12m2 stops
from $769per person
Hyannis
12h 40m2 stops
from $1,077per person
New Bedford
15h 10m4 stops
from $1,112per person
West Tisbury
14h 13m4 stops
from $1,319per person
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?

Flight prices are below average for this route right now.

Flights to Massachusetts from San Diego usually cost between $261 and $446 in October.
The lowest price found in the past 5 days was $236 on Southwest (Oct 27-Nov 3).

What is the cheapest San Diego to Massachusetts flight route?

The cheapest ticket to Massachusetts from San Diego found in the last 5 days was to Boston, at $178 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 5 days was $178.

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 $352 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 $470.

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

No, with an average price for the route of $399, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from San Diego to Massachusetts is January, when tickets cost $298 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $444 and $427 respectively.

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

Your flight ticket price will generally be cheaper if you fly to Massachusetts on a Saturday 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 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 47% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low season

January

Cheapest flight

$129
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 11% 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.

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 $180 one-way - $304 round-trip

Reviews of the 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
SouthwestOverall score based on 4190 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

6.0 GoodGordon, Jul 2026
Read more Southwest reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

There was over a 9 hour delay for one thing after another. A toilet problem, they had to change the brakes, they had to refuel, three pilots times out, etc. We had to sit on the plane at the gate for over 5 hours with no air.

Unfortunately it was not a good experience. There was a rude stewardess.

Very good. Plane was newly renovated so everything was very clean

My first leg was canceled 3 hr before leaving. My return trip left late. I leave it to Alaska higher ups to figure out what can be improved. Just put yourself in the passengers position.

This flight was miserable. Initially delayed due to weather in Las Vegas. Gate staff did not explain it was due to weather, blamed air traffic control which is harder to understand as it was a scheduled flight- ATC should know we were coming and the landing slot should have been secured. Airplane on the ground for 3 hours in San Diego. Then when the pilots got on, it required maintenance. Could have figured that out hours ago. Then when we got on the plan, pilots had to switch out which further delayed us. New pilot spent some time talking on the PA- wish he would have just gone up and flew the plane. Got in the air (finally). Then they canceled in flight service (they had time to serve, it was just an ERJ). Southwest serves a whole 737 on this route pretty much every time.

Several gate changes and then the plane kept getting delayed. The delay is understandable but this constant gate change I think twice or three times is just ridiculous.

We got in the plane late we still got to our destination on time. I wished Airlines would make people that put their luggage above were smaller maybe they would all fit and get them out easier customers like myself pay for her luggage in the back when your in a hurry to go to another destination it’s very frustrating for everyone to take their time to get their luggage down and wait because they don’t want to pay.

The plane smelled like an aquarium. Many passengers noted it smelled like fish. We then sat on the plane for over 2 hours before taking off

The flight was very late departing the gate, for unknown reasons.

Now that Spirit is not around Alaska took over the title of cheap and worse airlines with high prices for garbage cheap planes. Seats recline the entire 2”. What’s the purpose? Just make the stationary. Crew is on steroids. Food is like McDonald’s happy meal. Only happy in the name rest is garbage

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

We were told that the plane was new (2 years old) which was evident in that the seats weren’t as worn and the interior had a more modern look. The downside was that the crew said because it was new, WI-FI hadn’t been connected yet. Seems strange that a plane that is 2 years old hasn’t had a chance to connect to WIFI. And the airline knew this going into the flight so it would have been nice if they would have sent communication ahead of time to the passengers so we could download in flight entertainment. The flight was almost 5 hours long. There should have been WIFI for a flight for that duration.

Flight was delayed at airport with large backlog and WiFi was spotty

Flight was delayed from San Diego due to being overweight for weather conditions. We missed our connecting flight to our final destination due to the delay, as well as the connecting flight leaving before the scheduled departure time. We missed the connection within 10 - 15 minutes. We were booked on a later flight arriving 7 hours later. There were 7 passengers sharing the same originating and connecting flight.

Horrible, mismanaged ground issue resulting in a long delayed, next flight left early, waiting extra 7 hours in the airport, screen did not work

The internet on these planes stinks. Need to get starlink

Very good flight. Crew was great. No issues and we even arrived early.

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

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

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

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.

Delta flight was great from the check in all the way to arrival. However, I had a very bad experience. I requested a wheelchair and the wheelchair employee that went to pick me up from the plane in Boston to bring me to the baggage claims told me I have to pay him. I was under the impression that it was a free service and I usually give tips but the person forced me to pay and since I said no because I was upset with his demand when my daughter walked in to pick me up he demanded payment from my daughter who paid him thinking maybe now it is a charged service.

More space for economy, and the bathroom size is only for people with size XS

Well, true to American Airlines, both of my flights were delayed. But it’s a good thing that American is so consistently incompetent because if the first flight was delayed in the second flight was on time then I might’ve had a problem..

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.

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.

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

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

I paid for what I got which was cheap, I brought my own entertainment. I knew what to expect, so I could be prepared. If you’re flying economy, check in early like me. I have no problems with my flight, was on time, staff were friendly, and overall good experience.

Multiple maintenance delays and the missed and rebooked connection changed gates at least 6 times including one which had us walking 20 minutes to another terminal and then back again. Seated our family of three in different middle seats throughout the plane and then there was an empty seat next to me. Very long travel day which I would have never agreed to if I knew the itinerary would be changed at 5 am, 2 hours before takeoff.

JetBlue cancelled the flight. We had to rebook on another airline.

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

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

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.

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.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

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.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Always like Jet Blue! It seems, however, that people are getting bigger & seats are getting smaller! We had a very full flight and I couldn't get an aisle seat like I always do. I wish there were more leg room. People sitting next to me were very nice though so it was fine to disturb them if I needed to use the restroom. Otherwise the flight was fine but a bit long.

None of the in flight Direct TV worked. A better selection of Shows would have been better. The baggage was s low. Otherwise we enjoyed our flight!

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