$93 Find Cheap Flights from San Jose to Massachusetts - Compare and Save

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 Jose to Massachusetts departing on 8/5. 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 Jose to Massachusetts.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Massachusetts.
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Cheap Flights from San Jose to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$185
Albany
Albany1 stop$324
Boston
Boston1 stop$185
Albany
Albany1 stop$324

Book Cheap San Jose 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 Jose 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 Jose to Massachusetts

Tue, Aug 4 - Tue, Aug 18
Southwest Logo
11:30 am - 12:25 am
SJC
-
BOS
9h 55m
1 stop
Southwest Logo
9:05 am - 4:25 pm
BOS
-
SJC
10h 20m
1 stop
$185Southwest
Wed, Aug 19 - Sat, Aug 22
Southwest Logo
11:30 am - 12:25 am
SJC
-
BOS
9h 55m
1 stop
Southwest Logo
5:50 am - 11:30 am
BOS
-
SJC
8h 40m
1 stop
$202Southwest
Sat, Aug 15 - Tue, Aug 18
Southwest Logo
1:20 pm - 12:25 am
SJC
-
BOS
8h 05m
1 stop
Southwest Logo
9:05 am - 5:25 pm
BOS
-
SJC
11h 20m
1 stop
$213Southwest
Tue, Oct 27 - Tue, Nov 3
Delta Logo
7:15 am - 8:10 pm
SJC
-
BDL
9h 55m
1 stop
Delta Logo
5:05 pm - 10:58 pm
BDL
-
SJC
8h 53m
1 stop
$293Delta
Tue, Oct 27 - Tue, Nov 3
United Airlines Logo
6:40 am - 11:57 pm
SJC
-
BDL
14h 17m
2 stops
United Airlines Logo
5:04 pm - 10:36 pm
BDL
-
SJC
8h 32m
1 stop
$298United Airlines
Tue, Oct 27 - Tue, Nov 3
American Airlines Logo
7:16 pm - 9:03 am
SJC
-
BDL
10h 47m
2 stops
American Airlines Logo
11:29 am - 10:16 pm
BDL
-
SJC
13h 47m
2 stops
$303American Airlines
Thu, Oct 1 - Wed, Oct 7
Delta Logo
12:46 pm - 11:55 pm
SJC
-
ALB
8h 09m
1 stop
Delta Logo
9:50 am - 4:16 pm
ALB
-
SJC
9h 26m
2 stops
$329Delta
Tue, Aug 18 - Thu, Aug 27
American Airlines Logo
6:00 am - 9:27 pm
SJC
-
ALB
12h 27m
2 stops
American Airlines Logo
7:00 am - 1:40 pm
ALB
-
SJC
9h 40m
1 stop
$358American Airlines
Tue, Aug 25 - Wed, Aug 26
United Airlines Logo
6:20 am - 9:12 am
SJC
-
ACK
23h 52m
2 stops
United Airlines Logo
3:59 pm - 11:46 am
ACK
-
SJC
22h 47m
2 stops
$847United Airlines
Sat, Jun 27 - Wed, Jul 1
Multiple Airlines Logo
6:37 pm - 2:55 pm
SJC
-
HYA
17h 18m
2 stops
Multiple Airlines Logo
12:50 pm - 11:54 pm
HYA
-
SJC
14h 04m
2 stops
$938Multiple Airlines
Booking Insights

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

Get data-powered insights and trends into flights from San Jose 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 Jose, California 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 Jose, California to Massachusetts departing in August.

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

The average price for all round-trip flights from San Jose 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 $127 on average. The most expensive time of day to fly to Massachusetts is generally at night, which is peak travel time and where the average cost of a ticket is $127.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Jose 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 Jose to Massachusetts is December, when tickets cost $118 (return) on average. On the other hand, the most expensive months are March and February, when the average cost of round-trip tickets is $277 and $256 respectively.

How far in advance should I book a flight from San Jose 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 Jose 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 Jose to Massachusetts, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$93
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from San Jose to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from San Jose 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 Jose to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Jose to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Jose 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 Jose 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 Jose 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 Jose 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 Jose to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

 
See real verified KAYAK customer reviews for airlines flying from San Jose 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 Jose 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 12514 reviews
7.1Food
7.0Entertainment
8.5Crew
8.1Boarding
7.8Comfort
Airline reviews

Internet was great. It was nice to watch a movie. The crew was very nice.

10.0 ExcellentAnonymous, May 2026
PDX - BOS
Read more Alaska Airlines reviews

Internet was great. It was nice to watch a movie. The crew was very nice.

Thank you to everyone, the crew and pilots.. they were so amazing!!

Some food or at least snacks need to be offered on long flights. I thought I had ordered food for my husband and I prior to the flight, but was told during the flight that I had not. Perhaps, if you must charge extra for food, let people order on board. We did get some food, which evidently others had decided they didn’t want onboard, but it wasn’t very good. We did like the adherence to takeoff and landing times, and the quick return of our luggage.

Pretty smooth ride!… a little tight in the back and would’ve loved to had a movie screen… couldn’t beat the price to the West Coast!

No complimentary snacks or food. Had to buy drinks and food.

in-flight wifi was not working well. also the cabin temperature was a bit hot.

Plane was clean, staff was professional and flight was on time. No built in tv was still ok, as programs were offered that could synch to smart phones.

J was in the ER x 3...3 protruding discs...contacted Alaska many many days prior to cancel and request a refund or a credjt.. they only gave me 50 % credit....outrageous seeing how i have a doctors letter....just plain inhuman. AI sucks!

There is nothing critical to complain about but I would say the snacks are pretty bad Airline staff could be aggressive the way they move through the aisles and the plane I also got hustled for a small wallet size men bag and force the consolidated with my carry on item we're talking about a wallet size bag.

I wasn’t able to check in prior to arriving at the airport, I was told by the agent I may not get a seat on the plane as others were waiting for seats, I sat there for 2 hours before being assigned a seat, very stressful. The plane was delayed. Overall not a great travel experience for a 44 minute flight.

Was fine, delayed and feels like southwest is always late

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

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

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Flight delayed four separate times. I’m now one hour hours late to landing.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

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

The gate experience at LAX was abysmal (same for the arrival experience two days prior). Despite the LAX -> SAT schedule of two flights daily, our departure gate was at a smaller hub that we had to be bussed to from Terminal 4. Fortunately, I arrived at LAX extra early and had time to spare, but if I had not known, I might have missed my flight. I looked at the LAX airport map in the AA app and there was no indication of the additional boarding process. Lastly the gate area we were bussed to was crowded with limited food and beverage options. On flight, the fight attendant was hospitable and attentive, the flight was smooth, and AA's free (and working) wifi for AA members were all on the positive side.

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

The flight from LA to Chicago was smooth and service was very good overall.

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

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.

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

It was good. I’m very disappointed that they don’t give commentary ear pods for the movie. I forgot mine at home

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

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.

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

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

Information on your arrival and departure airports