$104 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 9/11. 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$247
Albany
Albany1 stop$325
Boston
Boston1 stop$247
Albany
Albany1 stop$325

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

Sun, Aug 31 - Fri, Sep 5
American Airlines Logo
6:00 am - 5:26 pmSJC-BOS
8h 26m1 stop
American Airlines Logo
1:13 pm - 6:35 pmBOS-SJC
8h 22m1 stop
$247American Airlines
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Sat, Sep 13 - Sat, Sep 20
American Airlines Logo
6:00 am - 8:04 pmSJC-BOS
11h 04m1 stop
American Airlines Logo
6:00 am - 12:39 pmBOS-SJC
9h 39m1 stop
$249American Airlines
Find Deal
Tue, Sep 16 - Tue, Sep 23
Alaska Airlines Logo
12:52 pm - 12:27 amSJC-BOS
8h 35m1 stop
Alaska Airlines Logo
7:20 am - 2:21 pmBOS-SJC
10h 01m1 stop
$250Alaska Airlines
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Sun, Oct 19 - Wed, Oct 29
Alaska Airlines Logo
6:25 am - 5:43 pmSJC-BOS
8h 18m1 stop
Alaska Airlines Logo
4:24 pm - 10:37 pmBOS-SJC
9h 13m1 stop
$263Alaska Airlines
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Tue, Aug 19 - Thu, Sep 11
Southwest Logo
8:55 pm - 8:10 amSJC-BOS
8h 15m1 stop
Southwest Logo
5:15 am - 10:30 amBOS-SJC
8h 15m1 stop
$264Southwest
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Sat, Aug 23 - Fri, Aug 29
Southwest Logo
8:55 pm - 8:10 amSJC-BOS
8h 15m1 stop
Southwest Logo
7:30 am - 3:50 pmBOS-SJC
11h 20m1 stop
$269Southwest
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Wed, Oct 15 - Tue, Oct 21
United Airlines Logo
6:30 am - 5:02 pmSJC-BOS
7h 32m1 stop
United Airlines Logo
12:35 pm - 6:14 pmBOS-SJC
8h 39m1 stop
$270United Airlines
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Wed, Oct 15 - Tue, Oct 21
United Airlines Logo
8:45 am - 12:50 amSJC-BOS
13h 05m2 stops
United Airlines Logo
12:35 pm - 6:14 pmBOS-SJC
8h 39m1 stop
$275United Airlines
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Sat, Sep 13 - Wed, Sep 17
Delta Logo
11:15 am - 11:53 pmSJC-BOS
9h 38m1 stop
Delta Logo
6:15 am - 12:50 pmBOS-SJC
9h 35m1 stop
$277Delta
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Mon, Oct 20 - Sat, Nov 1
Delta Logo
6:00 pm - 6:35 amSJC-BOS
9h 35m1 stop
Delta Logo
3:20 pm - 10:17 pmBOS-SJC
9h 57m1 stop
$307Delta
Find Deal
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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from San Jose to Massachusetts.

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 July and August, when the average cost of round-trip tickets is $395 and $380 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, Wednesday 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 Wednesday 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$104
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from San Jose to Hartford

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 $425.

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
SouthwestOverall score based on 4241 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

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.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

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.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

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.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

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

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

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.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

It was too hot in the cabin. The AC did not help.

Love the mosaic program, being able to move to an extra space seat for free is awesome

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.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

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

Eventless. It was a good flight and good crew. Can’t complaint.

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

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

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