$125 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 2/24. 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.
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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$251
Albany
Albany1 stop$380
Boston
Boston1 stop$251
Albany
Albany1 stop$380

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

Wed, Feb 25 - Tue, Mar 3
Alaska Airlines Logo
10:16 am - 11:59 pm
SJC
-
BOS
10h 43m
1 stop
Alaska Airlines Logo
9:02 am - 5:09 pm
BOS
-
SJC
11h 07m
1 stop
$251Alaska Airlines
Wed, Mar 4 - Wed, Mar 11
Alaska Airlines Logo
7:40 am - 3:36 pm
SJC
-
BOS
28h 56m
1 stop
Alaska Airlines Logo
4:36 pm - 10:54 am
BOS
-
SJC
21h 18m
1 stop
$254Alaska Airlines
Sat, Feb 28 - Wed, Mar 4
Delta Logo
6:20 am - 7:15 pm
SJC
-
BOS
9h 55m
1 stop
Delta Logo
7:30 am - 2:56 pm
BOS
-
SJC
10h 26m
1 stop
$257Delta
Thu, Feb 19 - Wed, Feb 25
Alaska Airlines Logo
7:10 pm - 6:54 am
SJC
-
BOS
8h 44m
1 stop
Alaska Airlines Logo
7:00 am - 1:42 pm
BOS
-
SJC
9h 42m
1 stop
$270Alaska Airlines
Mon, Feb 23 - Tue, Mar 3
Delta Logo
10:35 pm - 10:02 am
SJC
-
BOS
8h 27m
1 stop
Delta Logo
7:15 am - 1:37 pm
BOS
-
SJC
9h 22m
1 stop
$277Delta
Tue, Feb 24 - Thu, Feb 26
Southwest Logo
12:10 pm - 10:30 pm
SJC
-
BOS
7h 20m
1 stop
Southwest Logo
5:20 am - 12:40 pm
BOS
-
SJC
10h 20m
2 stops
$279Southwest
Mon, Mar 9 - Wed, Mar 11
United Airlines Logo
10:55 pm - 10:50 am
SJC
-
BOS
8h 55m
1 stop
United Airlines Logo
6:00 am - 1:41 pm
BOS
-
SJC
10h 41m
2 stops
$282United Airlines
Tue, Feb 24 - Thu, Feb 26
American Airlines Logo
6:00 am - 7:47 pm
SJC
-
BOS
10h 47m
2 stops
American Airlines Logo
5:30 am - 1:17 pm
BOS
-
SJC
10h 47m
1 stop
$286American Airlines
Mon, Mar 9 - Wed, Mar 11
United Airlines Logo
10:55 pm - 11:10 am
SJC
-
BOS
9h 15m
2 stops
United Airlines Logo
6:00 am - 1:41 pm
BOS
-
SJC
10h 41m
2 stops
$287United Airlines
Sat, May 9 - Tue, May 12
Southwest Logo
9:45 pm - 8:10 am
SJC
-
BDL
7h 25m
1 stop
Southwest Logo
12:25 pm - 6:15 pm
BDL
-
SJC
8h 50m
1 stop
$372Southwest
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 February.

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 February, when tickets cost $322 (return) on average. On the other hand, the most expensive months are November and April, when the average cost of round-trip tickets is $395 and $392 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 26 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$125
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 7% 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.

  • 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 $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.

  • How many flights are there between San Jose and Massachusetts per day?

    Each day, there are between 1 and 3 nonstop flights that take off from San Jose and land in Massachusetts, with an average flight time of 5h 48m. The most common departure time is 7:00 am and most flights take off in the morning, while the most flights land at Boston. Each week, there are 4 flights. The most frequent day of departure is Monday, when 75% of all weekly flights depart. The fewest flights depart on a Tuesday.

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 11811 reviews
7.1Food
8.5Crew
7.0Entertainment
7.8Comfort
8.1Boarding
Airline reviews

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.

6.0 Goodrsmrostov, Jan 2026
SEA - BOS
Read more Alaska Airlines reviews

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.

The flight attendants were excellent and I was in the back of the plane. Much much better than recent JetBlue experiences on that route and better than Delta on that route.

Larger seats and more room would elevate the experience. Otherwise, it was good!

Check in went pretty well and you didn't lose my bag. After I got a drink from the drink cart they charged me for it, and at the crazy overpriced airport rates. Never had that happen before, is that an american thing? what madness.

I was delayed several times. Missed a very important event. The airline only provided a $12 voucher after being delayed 3 times.

One the nicest and great air crews I’ve experienced and I’ve flown a lot

I don’t want to pay extra to choose my seat

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.

Great flight but super high price. Glad it was a business trip and not personal

3 hour delay. Had to change plans and was still delayed.

We got exit row seats both flights. Everything was running on time

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.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

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

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

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

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

The flight crew where really good. Better then the crew from BNE to SFO

left on time, reasonable boarding process arrived early luggage came out quickly

I like flying first class, and United has a nice one

I’m so sorry, I can’t remember her name, I believe it was Dimpti. She was stellar, also a mature Asian flight attendant, lots of flowers in her hair, just as amazing! But literally the crew was AWESOME . Only downside is there weren’t any charging outlets. Maybe I needed to ask a flight attendant , but it would’ve been nice to have one easily accessible.

I boarded flight UA#1318 at Sacramento International Airport going back to Houston TX. The flight was scheduled at 5:10am. I was able to check in virtually using the United Airlines app. When I entered the airport, there was no one outside assisting with checked bags as it was for Delta Airlines. Immediately upon entering, there was a LONG, EXTREMELY LONG line to the kiosks to get boarding passes. I stand in line to get boarding passes then had to move to ANOTHER EXTREMELY LONG line to get my bags checked in. While standing in this line, we noticed an agent taking customers to 3 at a time to her station to check their bags in. Lucky for me, she called me back, checked my bags for me and I was on my way. I then encountered another long line at the TSA check and to avoid I ending up having to sign up for CLEAR to bypass it. So glad, I did.,...Both of my flights were great with no issues, butthe check in progress at Bush Airport was so much smoother. Check-in at SMF airport needs to be anaylzed and corrected. Do better United, I know you can....thanks

Pushed back only to get deplaned due to a tire damaged by ground crew. They did at least go pretty fast. The bathrooms should be banned under the Geneva convention. No room to even sit straight on the toilet. The under-seat entertainment units block what little leg room there is.

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

Older aircraft, no meal, only food was for purchase. Not impressed United.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

It would be nice to have some low carb options in the snacks.

No enough space plus only allowing one laggage instead of two like other airlines.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

Qatar airways ,boarding arrangements at Hamid international airport could been better

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

The flight was on time and arrived early. The crew were friendly and helpful.

Overall experience was great. Flights were almost on time in departing and we arrived at our destination as scheduled. No issues with amenities or flight crew. Everything went well as as expected. Will fly again with American Airlines in the future!

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

The flight was flawless and we even arrived between 20 and 25 minutes early!

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

Information on your arrival and departure airports