$133 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 8/5. 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$265
Albany
Albany1 stop$381
Boston
Boston1 stop$265
Albany
Albany1 stop$381

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

Wed, Aug 19 - Tue, Aug 25
Southwest Logo
12:45 pm - 12:25 am
OAK
-
BOS
8h 40m
1 stop
Southwest Logo
9:05 am - 4:35 pm
BOS
-
OAK
10h 30m
1 stop
$265Southwest
Wed, Aug 12 - Wed, Aug 19
Southwest Logo
12:45 pm - 12:25 am
OAK
-
BOS
8h 40m
1 stop
Southwest Logo
9:05 am - 4:35 pm
BOS
-
OAK
10h 30m
1 stop
$266Southwest
Wed, Aug 5 - Tue, Aug 11
Southwest Logo
12:45 pm - 12:25 am
OAK
-
BOS
8h 40m
1 stop
Southwest Logo
9:05 am - 4:35 pm
BOS
-
OAK
10h 30m
1 stop
$281Southwest
Wed, Aug 12 - Wed, Aug 19
Southwest Logo
12:45 pm - 12:25 am
OAK
-
BOS
8h 40m
1 stop
Southwest Logo
5:25 am - 12:40 pm
BOS
-
OAK
10h 15m
2 stops
$286Southwest
Wed, Nov 4 - Sat, Nov 7
Southwest Logo
7:10 am - 7:40 pm
OAK
-
BOS
9h 30m
1 stop
Southwest Logo
9:00 am - 4:55 pm
BOS
-
OAK
10h 55m
1 stop
$294Southwest
Mon, Aug 31 - Wed, Sep 2
Southwest Logo
12:30 pm - 12:25 am
OAK
-
BOS
8h 55m
1 stop
Southwest Logo
9:05 am - 4:35 pm
BOS
-
OAK
10h 30m
1 stop
$295Southwest
Tue, Aug 11 - Fri, Aug 14
Southwest Logo
12:45 pm - 12:25 am
OAK
-
BOS
8h 40m
1 stop
Southwest Logo
3:55 pm - 11:05 pm
BOS
-
OAK
10h 10m
1 stop
$296Southwest
Sat, Jul 18 - Tue, Jul 21
Delta Logo
5:30 pm - 6:05 am
OAK
-
BOS
9h 35m
1 stop
Delta Logo
6:05 am - 11:46 am
BOS
-
OAK
8h 41m
1 stop
$297Delta
Wed, Nov 4 - Sat, Nov 7
Southwest Logo
7:05 pm - 8:05 am
OAK
-
BOS
10h 00m
2 stops
Southwest Logo
9:00 am - 4:55 pm
BOS
-
OAK
10h 55m
1 stop
$300Southwest
Fri, Jul 3 - Mon, Jul 6
Multiple Airlines Logo
7:13 pm - 2:04 pm
OAK
-
MVY
15h 51m
2 stops
Multiple Airlines Logo
7:00 am - 7:33 pm
MVY
-
OAK
15h 33m
2 stops
$1,776Multiple 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 August.

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 December and April, when the average cost of round-trip tickets is $362 and $293 respectively.

Good to know

Low seasonSeptember
Cheapest flight$133
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 7% 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.
7.9
Alaska AirlinesOverall score based on 12521 reviews
7.0Entertainment
7.8Comfort
8.5Crew
7.1Food
8.1Boarding
Airline reviews

Never had so many staff members be rude and disrespectful. I had a staff member sarcastically call me “girly” after making me wait 20 minutes to be seen by her. I was able to print my luggage tag and she told me I was too late to check luggage I said the system obviously disagrees. And you had me wait way too long while you asked every single passenger ahead of me about their Disney vacations. She wasted so much time to then say “girly your bag won’t make it on the plane” I’m not her girly I’m a full grown adult. She needs to learn a hell of a lot of respect

2.0 MediocreBridget, Jun 2026
SNA - SEA
Read more Alaska Airlines reviews

Never had so many staff members be rude and disrespectful. I had a staff member sarcastically call me “girly” after making me wait 20 minutes to be seen by her. I was able to print my luggage tag and she told me I was too late to check luggage I said the system obviously disagrees. And you had me wait way too long while you asked every single passenger ahead of me about their Disney vacations. She wasted so much time to then say “girly your bag won’t make it on the plane” I’m not her girly I’m a full grown adult. She needs to learn a hell of a lot of respect

My flight was several times rescheduled and then finally canceled.

The flight itself was great. But we had to wait over an hour to deplane so I missed my train. Not the crews fault. They were wonderful!

Flying into PAE was so easy because it’s baggage claim is quick and accesible. I had a car rental and the counter is inside the baggage claim area, very convenient.

It was a very short flight so there really wasn’t any entertainment my. The little pretzels were good though and the cabin crew was awesome.

The first flight was fine, great crew, but the plane was delayed 45 minutes to go to Seattle because of they were missing a ramp. That would make sense if the plane was actually at the gate. Not if we’re still waiting for a plane. After we landed we waited 30-45 minutes on the tarmac just to get off the plane. Alaska made me miss my connecting flight, wasting my time, and my money. I should honestly be reimbursed, but hey, when does the airline ever actually take accountability? Never.

Over all it was great. My original flight was canceled but they quickly rebooked me. I was frustrated because I had to cancel my entire plans for the day but all considered, not bad. The crew tried to keep us calm while we sat in the plane for was felt was an hour or so but they could use a bit of a script. The seats were comfortable and I would give it another try.

Flight delayed Didn’t send second leg of trip itemerary First class was fair, but not great.

Short trip, was nice to have a drink on the short flight still.

Not able to get boarding pass for domestic connection flight when check in at international airport. I was told I need to get connection flight boarding pass after I entered US. It us very inconvenient.

Was fine, delayed and feels like southwest is always late

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

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.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

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.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Flight delayed four separate times. I’m now one hour hours late to landing.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

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

The tray table was broken and the food was terrible.

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

N Everything was perfect from boarding to assistance to baggage in Tampa

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

It was good. I’m very disappointed that they don’t give commentary ear pods for the movie. I forgot mine at home

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

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.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

Everything you need to know for your flight from Oakland to Massachusetts

Information on your arrival and departure airports