$81 Find Cheap Flights from San Jose 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 Jose to Massachusetts departing on 11/5. 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

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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$267
Albany
Albany1 stop$334
Boston
Boston1 stop$267
Albany
Albany1 stop$334

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, Oct 28 - Sat, Nov 1
American Airlines Logo
6:00 am - 5:23 pmSJC-BOS
8h 23m1 stop
American Airlines Logo
2:47 pm - 10:06 pmBOS-SJC
10h 19m1 stop
$267American Airlines
Find Deal
Tue, Nov 4 - Tue, Nov 11
Southwest Logo
7:40 pm - 8:15 amSJC-BOS
9h 35m2 stops
Southwest Logo
5:30 am - 11:30 amBOS-SJC
9h 00m1 stop
$269Southwest
Find Deal
Mon, Jan 5 - Wed, Jan 14
Alaska Airlines Logo
7:07 pm - 7:48 amSJC-BOS
9h 41m1 stop
Alaska Airlines Logo
4:20 pm - 10:27 pmBOS-SJC
9h 07m1 stop
$273Alaska Airlines
Find Deal
Tue, Dec 9 - Tue, Dec 16
Alaska Airlines Logo
11:16 am - 11:59 pmSJC-BOS
9h 43m1 stop
Alaska Airlines Logo
4:24 pm - 10:57 amBOS-SJC
21h 33m1 stop
$276Alaska Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
Delta Logo
1:25 pm - 11:40 pmSJC-BOS
7h 15m1 stop
Delta Logo
6:47 pm - 11:59 pmBOS-SJC
8h 12m1 stop
$277Delta
Find Deal
Wed, Oct 1 - Tue, Oct 7
Delta Logo
12:35 pm - 11:52 pmSJC-BDL
8h 17m1 stop
Delta Logo
6:10 am - 2:42 pmBDL-SJC
11h 32m2 stops
$282Delta
Find Deal
Wed, Oct 29 - Tue, Nov 4
United Airlines Logo
6:40 pm - 5:56 amSJC-BOS
8h 16m1 stop
United Airlines Logo
9:30 am - 6:48 pmBOS-SJC
12h 18m2 stops
$296United Airlines
Find Deal
Wed, Oct 29 - Tue, Nov 4
United Airlines Logo
6:40 pm - 7:34 amSJC-BOS
9h 54m2 stops
United Airlines Logo
5:30 am - 1:42 pmBOS-SJC
11h 12m2 stops
$301United Airlines
Find Deal
Wed, Oct 1 - Tue, Oct 7
 Logo
11:40 am - 11:13 amSJC-BOS
20h 33m2 stops
 Logo
8:01 am - 3:05 pmBOS-SJC
10h 04m1 stop
Thu, Oct 2 - Tue, Oct 7
 Logo
11:40 am - 11:13 amSJC-BOS
20h 33m2 stops
 Logo
8:01 am - 3:05 pmBOS-SJC
10h 04m1 stop
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.

What is the cheapest San Jose 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 Jose found in the last 72 hours was to Boston, at $127 round-trip. The most popular route is from San Jose (SJC) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $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 November, when tickets cost $302 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $377 and $377 respectively.

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

The average price of all round-trip flights from San Jose to Massachusetts clicked on KAYAK for each day over the last 12 months.

For San Jose to Massachusetts, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Massachusetts back to San Jose, the best deals are generally found on Thursday, with Monday being the most expensive.

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 26 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$81
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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.

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

    The cheapest time of day to fly to Massachusetts is generally in the evening, when round-trip flights cost $361 on average. Morning departures are around 2% more expensive than evening flights, 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 $395.

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.
8.0
Alaska AirlinesOverall score based on 10000 reviews
7.0Entertainment
8.1Boarding
8.5Crew
7.1Food
7.8Comfort
Airline reviews

The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.

10.0 ExcellentAnonymous, Sep 2025ONT - PDX
Read more Alaska Airlines reviews

The first leg of the trip was excellent. Lovely flight attendants and comfortable plane. The second leg left a lot to be desired. The flight attendant was rude when I asked for a Diet Coke, the boarding required quite a long walk and the plane was crammed and uncomfortable.

Flight attendant was awful, I felt second hand embarrassment with every one of her interactions with people onboard. She was so incredibly rude every chance she got

I was sitting towards back of plane and the flight attendants I thought spoke unusually loud for an evening flight. They chatted and chatted all night long and it seemed odd to me that they didn’t try to lower their voices. It is annoying as a passenger to hear all their conversations.

Staff at Gate desk were helpful. My connecting flight from the first part of my trip Kona to Seattle was late. I had to run through SeaTac Seattle to catch my flight to San Jose. They made an exception to let me board. On my return trip San Jose to San Diego and San Diego to Honolulu the same thing happened. One flight arrived late and I had to run through the terminal to catch my connection. There are no Gluten-free & Vegan options meals and snacks to purchase.

Short flight was fine, but no entertainment and bathrooms broken.

My email notifications were silenced, so I didn't get word that the departing flight had changed gates. It wasn't until I noticed that few people had gathered for the flight that I checked the airport schedule board, 20 minutes before boarding. I then told several people at the old gate of the change. If I was to receive a text I would have been notified of the change earlier, Or to hear an announcement over the airport intercom.

delayed flight 3 hours, then took 45 min to get to gate and another 10 min to open door

Not having to pay 160$ for a 20 lb and 12 lb bag that were clearly under 50 lbs and they overcharged me for them

Great crew, smooth flight and landing. Wish they would offer Dr. Pepper and a choice of flavors of pretzels.

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

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

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.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

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.

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.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely

Boarded plane and then delayed 1.5 hours while on the plane

Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.

Really good 😊 the woman at the gate entrance was a little rude checking in our carry-on but i dont think she worked for the airline, she worked for the airport at sacramento, other than that amazing.

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

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.

4 hours late, including over +1 hour waiting in plane to take off. Baggage left behind too.

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

Was not able to watch most shows on the entertainment site. They would not load

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

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.

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