$152 Find Cheap Flights from Oakland 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 Oakland to Massachusetts departing on 10/3. 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.
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Cheap Flights from Oakland to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$303
Albany
Albany1 stop$311
Boston
Boston1 stop$303
Albany
Albany1 stop$311

Book Cheap Oakland 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 Oakland 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 Oakland to Massachusetts

Tue, Sep 15 - Tue, Sep 22
Alaska Airlines Logo
6:52 pm - 6:09 am
OAK
-
BOS
8h 17m
1 stop
Alaska Airlines Logo
8:00 am - 6:12 pm
BOS
-
OAK
13h 12m
1 stop
$303Alaska Airlines
Tue, Sep 8 - Tue, Sep 22
Southwest Logo
11:55 pm - 11:35 am
OAK
-
ALB
8h 40m
1 stop
Southwest Logo
4:15 pm - 10:30 pm
ALB
-
OAK
9h 15m
1 stop
$311Southwest
Mon, Aug 31 - Sat, Sep 5
Alaska Airlines Logo
1:29 pm - 5:49 am
OAK
-
BOS
13h 20m
1 stop
Alaska Airlines Logo
8:00 am - 7:52 pm
BOS
-
OAK
14h 52m
1 stop
$313Alaska Airlines
Tue, Sep 8 - Tue, Sep 22
Southwest Logo
11:55 pm - 11:35 am
OAK
-
ALB
8h 40m
1 stop
Southwest Logo
12:50 pm - 7:50 pm
ALB
-
OAK
10h 00m
2 stops
$316Southwest
Mon, Aug 31 - Fri, Sep 4
Alaska Airlines Logo
5:10 pm - 5:49 am
OAK
-
BOS
9h 39m
1 stop
Alaska Airlines Logo
6:17 pm - 6:12 pm
BOS
-
OAK
26h 55m
1 stop
$323Alaska Airlines
Mon, Sep 21 - Thu, Sep 24
Southwest Logo
11:55 pm - 11:35 am
OAK
-
ALB
8h 40m
1 stop
Southwest Logo
6:05 pm - 11:10 pm
ALB
-
OAK
8h 05m
1 stop
$333Southwest
Wed, Sep 9 - Wed, Sep 16
Delta Logo
5:00 pm - 6:30 am
OAK
-
BOS
10h 30m
1 stop
Delta Logo
6:05 am - 11:59 am
BOS
-
OAK
8h 54m
1 stop
$337Delta
Wed, Sep 9 - Wed, Sep 23
Delta Logo
5:00 pm - 6:30 am
OAK
-
BOS
10h 30m
1 stop
Delta Logo
6:05 am - 11:59 am
BOS
-
OAK
8h 54m
1 stop
$337Delta
Thu, Aug 27 - Sun, Aug 30
Multiple Airlines Logo
12:13 pm - 6:15 am
OAK
-
BDL
15h 02m
1 stop
Multiple Airlines Logo
5:40 pm - 11:18 am
BDL
-
OAK
20h 38m
1 stop
$347Multiple Airlines
Thu, Oct 22 - Sun, Oct 25
Multiple Airlines Logo
12:13 pm - 6:15 am
OAK
-
BDL
15h 02m
1 stop
Multiple Airlines Logo
5:51 pm - 11:18 am
BDL
-
OAK
20h 27m
1 stop
$399Multiple Airlines
Booking Insights

KAYAK's insights & trends for Oakland to Massachusetts flights

Get data-powered insights and trends into flights from Oakland 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 Oakland, 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 Oakland, California to Massachusetts departing in September.

Flight prices are below average for this route right now.

Flights to Massachusetts from Oakland, California usually cost between $362 and $777 in September.
The lowest price found in the past 5 days was $303 on Alaska Airlines (Sep 15-Sep 22).

What is the cheapest month to fly from Oakland to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland 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 Oakland to Massachusetts is March, when tickets cost $0 (return) on average. On the other hand, the most expensive months are July and December, when the average cost of round-trip tickets is $617 and $591 respectively.

Good to know

Cheapest flight

$152
Most popular time to fly with an average 13% increase in price.
Flight from Oakland to Boston

FAQs - booking Massachusetts flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oakland 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 Oakland 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 Oakland 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 Oakland 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 Oakland 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 4 airlines serving from Oakland to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Oakland 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 Oakland 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 4230 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
Airline reviews

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.

8.0 ExcellentGreg, Oct 2025
OAK - BUR
Read more Southwest reviews

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.

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.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Southwest Airlines is behind the times with a woefully inefficient service animal policy that leads to major inconsistency and stress for passengers and crew alike. Despite so many attempts to share feedback and request better support, they bungled it once again and provoked a panic attack in the process, with no apologies or acknowledgment that their crew was failing to adhere to their own inadequate policies. WiFi didn’t work, flight was delayed by an hour, it was about what I’ve come to expect from Southwest these days.

Flights were full but SWA still managed to get everyone loaded and depart on time. No snack or beverage service on the first leg due to turbulance. Seats were clean but very little cushioning. Reasonable amount of leg room.

Our flight to Oakland was great bc the plane was new but it was delayed by 15min not bad at all. Over all it was an 8/10

Our flight to Vegas was delayed by almost two hours - I appreciated the updates but it was a bummer of a start to a celebratory trip. The delays meant we missed our dinner reservations we made a month ago so that was disappointing. Once we got to the gate, though, the crew did all they could to make up for the lost time and to keep it efficient and enjoyable, so I appreciate their efforts!!

There was a problem that delayed boarding for more than 20 min. and once everyone was on board, the plane did not take off for another 30 min. which then made our arrival in Phoenix 1 hour late.

Our two flights from GRR to MDW and MDW to OAK were both delayed due to weather. Be sure to build in a sufficient buffer in the transfer time to account for this type of problem. SW recommends connections as short as 40 min. Don't do this. We had to change concourses in MDW, a pretty long walk, to make our connection. Rule of thumb I use when traveling on flights with multiple legs is for connections of 80 min or more, unless there is no plane change, in which case it doesn't matter.

I always have flown Alaska Airlines because I never had an issues. Their customers service is incredible and an amazing communication.

Flight was canceled in good weather due to mechanical issue. Rebooked to flight to different airport in area that landed 7 hours after initially planned arrival. We had to jump through hoops to get taxi reimbursement given flight landed in different airport at 12:45 am.

My travel mate needed wheel chair assistance getting on and off, and it was excellent. Thank you!

Affirmed my disability by allowing me to board when most accessible. Very parable, helpful and friendly staff. Smooth flight overall! I always fly Alaska when possible! Thank you!

In both halves of the trip (going and returning) there were problems. Not exactly Alaska's fault, but still really difficult. Outgoing flight was canceled and rebooked twice due to a total ground stop of all Alaska's flights. This required me to change airports with minimal notice and I almost missed my flight transferring to the other airport (which was roughly an hour and a half away). On the return, the first leg was delayed by an hour, and the second leg was delayed by nearly 3 hours. This was a rough set of flights and the communication about all of these changes was minimal. Crew did their best however, so no fault there. Other thing to remember is there is no food on Alaska flights unless you pre-order. Take that into account when you choose airlines.

The setting on the loudspeaker was painful and the crew member who did the talking spoke very quickly and repetitively, with extra little jokes that were distracting and mostly unfunny. I doubt that the main messages penetrated the noise.

The Alaska app and website were not fully operational. I had to spend about 15 minutes at the counter doing things that should have been completed online. The agent was very nice and helpful, however.

Good. They checked my bag FOR FREE so I didnt have to try to hoist it up into the overhead compartment. Also, they served free beverages, which I appreciated.

From my interactions with the Oakland airport staff through TSA through the gate agents to the flight crew on Hawaiian they were just so kind professional and helpful.. the only thing I would add would be the they need more help and TSA and on the Hawaiian airlines flight it would be so much nicer for them to play beautiful Hawaiian music on the way over there.. they didn't start playing it until right before we landed..

Staff was very friendly. Flight was on time and arrived early. Flight was comfortable.

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.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

Flight was delayed multiple time and for more than 1 hr. My onward flight from BOS to MCI was also delayed. These delays have caused me so much inconvenience and Delta does nothing to ensure flights take off on time. No one knew why the inbound flight was delayed and what was the issue.

This flight was originally delayed by ~45 minutes; which is fine. However, there were additional delays due to late offboarding of the prior flight, unclear issues with the boarding process, delays on the tarmac, and exceptionally long taxiing. None of these issues were communicated proactively. Additionally, the flight had exceptionally rough turbulence, which led to a very uncomfortable flight and no traditional beverage service. Again, this is understandable, but it was not communicated up-front by the flight team.

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

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

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.

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

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.

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