$104 Find Cheap Flights from Oakland 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 Oakland to Massachusetts departing on 12/16. 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 Oakland to Massachusetts, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Massachusetts, as well as popular online travel agencies
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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$237
Albany
Albany2 stops$433
Boston
Boston1 stop$237
Albany
Albany2 stops$433

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

Fri, Dec 5 - Tue, Dec 9
Southwest Logo
12:35 pm - 10:45 pmOAK-BOS
7h 10m1 stop
Southwest Logo
1:35 pm - 6:40 pmBOS-OAK
8h 05m1 stop
$237Southwest
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Fri, Dec 5 - Tue, Dec 9
Southwest Logo
12:35 pm - 10:45 pmOAK-BOS
7h 10m1 stop
Southwest Logo
6:45 am - 1:55 pmBOS-OAK
10h 10m2 stops
$242Southwest
Find Deal
Tue, Feb 3 - Wed, Feb 11
Alaska Airlines Logo
10:30 am - 3:20 pmOAK-BOS
25h 50m1 stop
Alaska Airlines Logo
7:00 am - 4:23 pmBOS-OAK
12h 23m1 stop
$247Alaska Airlines
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Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
6:35 pm - 7:16 amOAK-BOS
9h 41m1 stop
Alaska Airlines Logo
10:00 am - 5:43 pmBOS-OAK
10h 43m1 stop
$251Alaska Airlines
Find Deal
Thu, Jan 29 - Mon, Feb 2
Alaska Airlines Logo
11:43 am - 11:59 pmOAK-BOS
9h 16m1 stop
Alaska Airlines Logo
7:00 am - 4:23 pmBOS-OAK
12h 23m1 stop
$255Alaska Airlines
Find Deal
Tue, Feb 3 - Wed, Feb 11
Southwest Logo
9:20 am - 10:30 pmOAK-BOS
10h 10m2 stops
Southwest Logo
6:50 am - 2:55 pmBOS-OAK
11h 05m1 stop
$282Southwest
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Tue, Feb 3 - Wed, Feb 11
Southwest Logo
9:35 am - 10:05 pmOAK-BOS
9h 30m2 stops
Southwest Logo
6:50 am - 2:35 pmBOS-OAK
10h 45m2 stops
$295Southwest
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Wed, Jan 7 - Tue, Jan 20
Delta Logo
12:38 pm - 11:56 pmOAK-BOS
8h 18m1 stop
Delta Logo
4:20 pm - 11:53 pmBOS-OAK
10h 33m1 stop
$297Delta
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Wed, Jan 7 - Sat, Jan 17
Delta Logo
5:55 am - 7:10 pmOAK-BOS
10h 15m2 stops
Delta Logo
4:25 pm - 9:38 pmBOS-OAK
8h 13m1 stop
$302Delta
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Fri, Dec 5 - Mon, Dec 8
Delta Logo
5:55 am - 9:26 pmOAK-BOS
12h 31m2 stops
Delta Logo
2:35 pm - 12:08 amBOS-OAK
12h 33m2 stops
$307Delta
Find Deal
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.

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 September, when tickets cost $329 (return) on average. On the other hand, the most expensive months are October and April, when the average cost of round-trip tickets is $486 and $477 respectively.

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

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

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

How far in advance should I book a flight from Oakland 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 Oakland 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 Oakland to Massachusetts, you should book around 3 weeks before departure, which saves you about 42% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$104
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 10% 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.

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

    The cheapest time of day to fly to Massachusetts is generally in the afternoon, when round-trip flights cost $327 on average. Morning departures are around 10% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is $427.

Reviews of the top 5 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
Alaska AirlinesOverall score based on 11231 reviews
7.0Entertainment
7.1Food
8.5Crew
7.8Comfort
8.1Boarding
Airline reviews

I recently traveled with my service animal, and before boarding, a gate agent kindly arranged for me to have an empty seat next to me to give my dog more space. However, once on board, a male crew member spoke to me in a rude and loud tone, insisting my dog stay on the floor or my lap—even after I explained what the gate agent had approved. His tone and behavior were unprofessional and made me feel uncomfortable in front of other passengers. I understand and respect airline policies, but I would appreciate if this could be reviewed to ensure better awareness and sensitivity toward passengers traveling with service animals. Thank you for your understanding.

6.0 GoodSofia, Oct 2025SAN - DCA
Read more Alaska Airlines reviews

I recently traveled with my service animal, and before boarding, a gate agent kindly arranged for me to have an empty seat next to me to give my dog more space. However, once on board, a male crew member spoke to me in a rude and loud tone, insisting my dog stay on the floor or my lap—even after I explained what the gate agent had approved. His tone and behavior were unprofessional and made me feel uncomfortable in front of other passengers. I understand and respect airline policies, but I would appreciate if this could be reviewed to ensure better awareness and sensitivity toward passengers traveling with service animals. Thank you for your understanding.

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.

Kayak I had marked one carry on, one checked bag. Yet when it completed the purchase marked it as no carry on. Fail on kayaks side! Then extended flight delayed due to computer issues. Crew of the plane did awesome but fail on both kayak and alaskan

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.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

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

It was the most expensive Alaska Airlines ticket I’ve ever purchased. I had a middle seat with no legroom or space compared to any other middle seat I’ve hadThere was a silver box under the seat that took up 70% of my legroom on the most narrow 737 max the crew flat out would not help they would not help with bags they would not help with garbage there was no coffee,It was definitely not one of my better experiences on Alaska.

Sitting on the ground for 2 hours waiting for a gate wasn't fun.

It was a great experience, friendly staff and good snacks

Online check in didn't work. Somehow ended up with 2 Alaska rewards numbers and 1 for Hawaiian. No one at check in could figure out what to do. No one at check in could help me confirm an upcoming flight on Hawaiian Airlines.

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.

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!

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

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.

The flight attendants were great, I joked with one I can’t remember her name, a blond, really sweet. I thought it was run well very professional. This was great i survived Spirit, I know for which I speak.

I was in first class. The outlets at my seat did not work. The plane was shabby and run down. I had prepurchsed a day subscription for internet that was not redeemable. I had to repurchase the internet for my flight and then it didn’t work anyway. Quite disappointed in what was supposed to be the launch of a great vacation.

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.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Friendly crew. Poor food service maybe due to full flight. All in all, you get what you pay for.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

very difficult boarding process - aggressive passengers not the friendliest crew

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.

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