$102 Find Cheap Flights from San Jose to Massachusetts - Compare and Save

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Cheap Flights from San Jose to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Boston
Boston1 stop$254
Albany
Albany1 stop$320
Boston
Boston1 stop$254
Albany
Albany1 stop$320
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?

Flight prices are below average for this route right now.

Flights to Massachusetts from San Jose, California usually cost between $302 and $390 in October.
The lowest price found in the past 5 days was $254 on Southwest (Oct 27-Nov 2).

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.

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

The cheapest month for flights from San Jose to Massachusetts is August, when tickets cost $338 (return) on average. On the other hand, the most expensive months are April and June, when the average cost of round-trip tickets is $522 and $484 respectively.

How far in advance should I book a flight from San Jose to Massachusetts?

To get a below average price on the flight from San Jose to Massachusetts, you should book around 2 weeks before departure, which saves you about 2% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low season

February

Cheapest flight

$102
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 22% 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

 
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 4188 reviews
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
Airline reviews

had to check bag at gate when there was still overhead bin space. As usual the WIFI didn't really work.

6.0 GoodAnonymous, Sep 2026
Read more Southwest reviews

had to check bag at gate when there was still overhead bin space. As usual the WIFI didn't really work.

The Southwest airline was ok. A big thank you to Kayak team (David), who worked with me on Sunday afternoon to rebook my travel from Burbank, CA, to CVG. My original flight on Sunday was delayed, so I had to cancel Sunday flight and rebook my travel to Monday. Could not have done it without help from David from Kayak team. Ante Soda GE Aerospace

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

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.

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.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

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.

Forget beverage, they didn't even have water for half the passangers?

Flight was not full! Had a whole row to myself.

Wifi didn’t work, no service, seats are hard as rocks

The crew were very respectful. And also they were welcoming.they did help us locate our seats.i enjoyed.

Terrible. Waited on runway for 1+ hour after landing and then was brought to wrong terminal

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

It was terrible, if they ran flights on time it would make a big difference.

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.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

Everything was great but the difference in paying for comfort + did not seem worth it.

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

Super friendly with lots of drink options an entertainment. Friendly crew.

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

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

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.

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

Excellent staff helping my 96 year old senior promptly with her oxygen needs

This flight was 2.5 hours delayed due to crew issues. This meant that we arrived after 2 AM. Very very inconvenient and we were not really kept well informed.

Crew was great and did their best to make us comfortable and captain came out at the beginning to announce why the flight was delayed, weather situation up ahead, and kept us updated throughout the flight.

A good, solid, no frills experience. Departed and arrived on time, staff were pleasant and attentive. Loved the Bluetooth connectivity on the SJC to IAH leg. Being able to watch movies and listen to them with my noise cancelling headphones was lovely. Missed that on the IAH to LHR leg (so I put the wired buds on and my over ear Quiet Comforts over those).

Had to pay for WiFi, delayed start, and sat on the runway forever.

On time departure was much appreciated. However, as a frequent flyer and American Advantage member, I was as disappointed not to get an aisle seat.

Flight was cancelled due to a myriad of operational issues. You guys really suck

Couldn't make the flight because connecting flight was canceled.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

Apart from the delay due to unforeseen circumstances. The leg from sjc to dfw was fine. It was the leg from dfw to orf that we encountered issues mainly due to the flight attendant crew not being friendly. We had two small children and we needed some assistance to warm up milk so the baby would sleep. The crew just didn’t get it and made things very difficult. One made a remark that the baby’s dirty diaper smell was a “gift” to the plane in a rude way. Normally I’d brush that off as a funny comment if the rest of the trip the attendants were helpful or understanding of the difficulty we faced. But that wasn’t the case. We were met with rudeness on the second leg. Whereas on the first leg the crew were so nice and helpful.

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!

Seat was surprisingly comfortable and roomy. I like the onboard “pantry”. Lavatory was kept very clean.

More options for your flight from San Jose to Massachusetts

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