$124 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 5/28. 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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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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Best Massachusetts Flight Deals from Oakland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Boston
Boston2 stops$202
Albany
Albany2 stops$284
Boston
Boston2 stops$202
Albany
Albany2 stops$284

Cheap Flights from Oakland to Massachusetts

 
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.

Recent round-trip flight deals from Oakland to Massachusetts

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Oakland to Massachusetts.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
11:51 am - 4:24 pmOAK-BOS
25h 33m2 stops
Spirit Airlines Logo
3:49 pm - 4:41 pmBOS-OAK
27h 52m3 stops
$202Spirit Airlines
Find Deal
Wed, May 28 - Fri, May 30
Spirit Airlines Logo
11:51 am - 4:24 pmOAK-BOS
25h 33m2 stops
Spirit Airlines Logo
10:04 am - 10:25 pmBOS-OAK
15h 21m2 stops
$214Spirit Airlines
Find Deal
Wed, May 28 - Fri, May 30
Alaska Airlines Logo
6:52 pm - 6:10 amOAK-BOS
8h 18m1 stop
Alaska Airlines Logo
7:30 am - 1:36 pmBOS-OAK
9h 06m1 stop
$257Alaska Airlines
Find Deal
Sat, May 24 - Wed, May 28
Hawaiian Airlines Logo
6:52 pm - 6:10 amOAK-BOS
8h 18m1 stop
Hawaiian Airlines Logo
7:30 am - 1:36 pmBOS-OAK
9h 06m1 stop
$260Hawaiian Airlines
Find Deal
Thu, May 29 - Wed, Jun 4
Alaska Airlines Logo
6:52 pm - 6:10 amOAK-BOS
8h 18m1 stop
Alaska Airlines Logo
6:00 am - 7:14 pmBOS-OAK
16h 14m1 stop
$277Alaska Airlines
Find Deal
Sat, May 24 - Sat, May 31
Southwest Logo
7:05 pm - 7:55 amOAK-ALB
9h 50m2 stops
Southwest Logo
1:55 pm - 8:40 pmALB-OAK
9h 45m1 stop
$284Southwest
Find Deal
Tue, Jul 15 - Tue, Sep 16
Southwest Logo
7:05 pm - 7:55 amOAK-ALB
9h 50m2 stops
Southwest Logo
1:55 pm - 8:45 pmALB-OAK
9h 50m2 stops
$289Southwest
Find Deal
Tue, Jul 15 - Tue, Sep 16
Delta Logo
5:15 pm - 6:09 amOAK-BOS
9h 54m1 stop
Delta Logo
6:00 am - 12:24 pmBOS-OAK
9h 24m1 stop
$297Delta
Find Deal
Wed, Sep 10 - Sat, Sep 13
Delta Logo
4:55 pm - 6:25 amOAK-BOS
10h 30m1 stop
Delta Logo
5:20 am - 11:56 amBOS-OAK
9h 36m2 stops
$302Delta
Find Deal
Sat, May 24 - Sat, May 31
Hawaiian Airlines Logo
7:58 pm - 8:00 amOAK-BOS
9h 02m1 stop
Hawaiian Airlines Logo
7:20 am - 1:36 pmBOS-OAK
9h 16m1 stop
$396Hawaiian Airlines
Find Deal
Tue, Sep 9 - Thu, Sep 18
Useful Info

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 August, when tickets cost $322 (return) on average. On the other hand, the most expensive months are April and March, when the average cost of round-trip tickets is $487 and $437 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.


Good to know

Low seasonJanuary
High seasonOctober
Cheapest flight$124
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 1% lower on average.
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.

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 9977 reviews
8.1Boarding
7.1Entertainment
7.9Comfort
8.5Crew
7.1Food
Airline reviews

Delayed flight due to mechanical issues. You only serve water or apple juice which is pathetic. To get to connecting flight you need to take a train so dumb. All in all it’s certainly not about the customer is it? You make that perfectly clear. It’s the last time I fly with you no matter how cheap your fares are!

2.0 MediocreShura, May 2025BUR - SEA
Read more Alaska Airlines reviews

Delayed flight due to mechanical issues. You only serve water or apple juice which is pathetic. To get to connecting flight you need to take a train so dumb. All in all it’s certainly not about the customer is it? You make that perfectly clear. It’s the last time I fly with you no matter how cheap your fares are!

My youngest didn't have a assigned seat until we biard6the plane.

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

There was no seating at the gate, no where to charge your devices, super crowded. Boarding in group F meant all luggage space was taken when it was time for me to board. The boarding crew was short with everyone and seemed irritated. The luggage space was insufficient, the seat was too small for me (6'4") and very uncomfortable trip. I was in a middle seat between a person snoring the whole trip and a person with very strong body odor. The flight crew was terse and unfriendly, seemed irritated and impatient. Yelled a lot at people with earbuds in, understandable. Finally, we arrived 10 minutes early, only to sit on the tarmac for 20 minutes and wait for a gate. Worst flight experience I've had in years.

Check your emails that you sent me. 9 emails were sent telling me that my flight is Delayed. Each one with a different time 7:10, 7:55, 9:31, 9:09, 9:29, 9:44, 10:00, 9:49, and 10:10. That was how my experience went.

It was my first time flying Alaska Airlines and first time flying from Santa Rosa airport. The staff was very professional and friendly. Their instructions were clear and any question was answered satisfactorily. My seat was comfortable and the in-flight beverage service very adequate for the duration of the flight. We arrived ahead of the scheduled landing time and deplaning was simple. I look forward to flying with Alaska again.

Personal demeanor not good on flight returning to LAX..Great and superb on the way to Portland

No non-alcoholic drinks available except water and small apple juice cans.

Flight attendant took my carefully folded coat and flung it across the aisle to the bin across the way. Where one of the passengers rescued it for me, because that just wasn’t right!!

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

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.

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.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a hell hole of an airport. It is the new LaGuardia. Everything Cobbled together. Security gates closed. Terri directional signage

Delta flight was on time, seats were comfortable, and crew was nice.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

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

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

I actually received a notification from kayak on email but not one by text from Delta when my departure gait changed and I almost missed my flight

New boarding doesn't make sense. Filling front first is slow.

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.

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Love the mosaic program, being able to move to an extra space seat for free is awesome

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

I paid for the service of having the right to choose my seat and it was not like that, they put me where they wanted and I explained to one of the staff that they were before boarding and they were very rude. I am traveling with the family and they put us in separate seats.

Little snafu at boarding. Staff communicated with gate poorly. Flight attendant was rude making disembark early. This was an older mint class. Needs an overhaul for sure. Food was good. The male flight attendant was really nice.

Everything was great except for some reason crew and ground crew could not figure out how to deal with an electric wheelchair and it delayed us 20-30mins. Was pretty frustrating for passengers and the captain.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

It was fast but uncomfortable seats. Had to pay a bit extra not sure why? Maybe in selection of all my 4 tix together ? Just knew I had a balance before getting boarding pass online when departing from satx ? And flight was delayed..

Last minute 2-3 hr delay in flight schedule; no explanation Unexpected extra $52 charge What's the benefit of choosing a cheap airline if you trick people last minute and force them to pay extra last minute? Did not appreciate being cornered.

We had a 5 hour delay, which resulted in my arriving at my final destination at 2 am instead of 9 pm

Seats are uncomfortable and too close together. Also, you missed my connection in Vegas on the way back and I ended up sleeping in the airport, flying back to Burbank instead of LAX and I got home 12 hours late.

Surprising everything went well. Nice attendants and fast getting on and off the plane. Overall, was happy with the experience.

Non-professional acting crew, Very uncomfortable seats…!! Very bad pricing with all the add-ons for seat choice, luggage fees, etc….soon you’ll charge extra for oxygen. The ticket price means Nothing because in the end, the actual amount i paid, i could have and will in the future continue to fly on a real airline…

The flight took an extra 30 min to take off because we were waiting for crew to board then it took another 30 min to get off the plane because there was no parking. Just overall ridiculous also please add a head rest my neck was gonna snap off thanks.

With this price, I shouldn't complain on anything. I understand I have to pay for every services they provide. The plane could smell a little better. Advise them to use frebeeze to freshen up the interior a little bit.

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